RAYMOND v. UNITED STATES (2024)

DECISION & ORDER

I. INTRODUCTION

On June 10, 2022, petitioner-defendants Andrew Raymond (“Raymond”) and Brian Requena (“Requena”), jointly represented by the same attorney, moved separately under 28 U.S.C. § 2255 to vacate, set aside or correct their sentences. Dkt. Nos. 356, 357. Because Raymond and Requena asserted ineffective-assistance claims against their former trial counsel, respondent United States of America (the “Government”) obtained Orders from Senior U.S. District Judge Norman A. Mordue finding that Raymond and Requena had waived their attorney-client privilege as to those claims. Dkt. Nos. 371, 373. Thereafter, the Government opposed both motions in a consolidated brief. Dkt. No. 386. Raymond and Requena filed a joint reply. Dkt. No. 391.

Both motions have been fully briefed and will be considered on the basis of the submissions without oral argument.¹

II. BACKGROUND

On March 12, 2015, a federal grand jury returned a two-count indictment that charged Raymond, Requena, and a man named Zefren Michael with a “synthetic” drug trafficking conspiracy (Count One) and with a promotional and international money laundering conspiracy (Count Two).

After the third man pleaded out, Dkt. No. 44, the Government obtained a two-count first superseding indictment that charged Raymond and Requena (collectively “defendants”) with the same synthetic drug trafficking (Count One) and money laundering (Count Two) crimes. Dkt. No. 63.

The Government's theory of the case against Raymond and Requena was somewhat complex. Dkt. No. 38. Briefly stated, defendants operated “Real Feel Products,” a company that manufactured and then distributed synthetic marijuana using chemical and pharmacological compounds sourced primarily from China. Real Feel employees would spray these “synthetic cannabinoids” onto leaf material that they would dry, package, and then ship out to smoke shops, including stores in the Northern District of New York.

The first superseding indictment identified six “synthetics” allegedly used in defendants’ operation: XLR11, PB-22, 5F-PB-22, AB-PINACA, 5-Fluoro-AB-PINACA, and APP-CHMINACA.² Although these six chemicals were not listed on the federal controlled substances Schedules maintained by the Drug Enforcement Administration (“DEA”), the Government alleged that these six compounds were “controlled substances analogues” within the meaning of the Controlled Substances Analogue Enforcement Act of 1986 (the “Analogue Act”), which criminalizes any substances with chemical and pharmacological properties that are “substantially similar” to a controlled substance listed on Schedule I or II.

The Government planned to use expert testimony from a chemist and a pharmacologist to prove that the six chemical compounds identified in the first superseding indictment were “substantially similar” to certain listed controlled substances on Schedule I.

The Government designated two DEA scientists Dr. Michael Van Linn, a chemist, and Dr. Jordan Trecki, a pharmacologist, as their experts. Between them, they had testified as Government witnesses in dozens of trials across the country. See Dkt. No. 131 at 31–35 (Dr. Van Linn); 35–37 (Dr. Trecki).

Defendants, for their part, also prepared for an expert battle. Raymond retained a team of lawyers for his defense. This included, as relevant here, attorneys Anthony Brooklier ³ and Donald Marks. Dkt. No. 357-3. Requena, for his part, only retained solo attorney Mark McBride. Dkt. No. 356-3.

The defense teams coordinated strategy. In advance of trial, they jointly moved to dismiss the synthetic drug trafficking conspiracy charge alleged in Count One on constitutional grounds. Dkt. No. 80. This motion to dismiss articulated a fairly technical argument about conflicting statutory definitions under the Analogue Act. Id. But after briefing, Dkt. Nos. 87, 90, Judge Mordue denied that motion on the papers, Dkt. No. 96.

Later, Raymond and Requena also filed separate-but-coordinated motions to preclude the testimony of the Government's experts or, in the alternative, for a hearing pursuant to Daubert v. Merrell Dow Pharms., Inc., 509 U.S. 579, 113 S.Ct. 2786, 125 L.Ed.2d 469 (1993). Dkt. Nos. 121, 123. But after briefing, Dkt. Nos. 131, 175, Judge Mordue denied both Daubert motions without a hearing, too.⁴ Dkt. No. 184.

The case finally went to trial on July 12, 2017. There, the Government's expert chemist Dr. Van Linn opined that the six chemical compounds named in the first superseding indictment were “unscheduled” during at least some of the relevant time period, and that each compound has a chemical or molecular structure that is “substantially similar” to a controlled substance listed in Schedule I.⁵ Tr. at 1500–31.⁶ Likewise, the Government’ expert pharmacologist Dr. Trecki opined that the six chemical compounds also have a hallucinogenic effect on the human nervous system that is “substantially similar” to that of the same corresponding set of controlled substances listed in Schedule I. Id. at 1631–62.

To rebut these Government experts, Raymond and Requena put on their own experts: Dr. Anthony DeCaprio (pharmacology) and Dr. Mark Erickson (chemistry). Dkt. No. 183. During the defense's case, Dr. DeCaprio opined that it is not possible to reach any scientifically sound conclusion as to the pharmacological effects of the synthetic substances named in the indictment without human testing. Tr. at 1830–32. Likewise, Dr. Erickson opined that there is no good scientific basis on which to determine whether one substance has a chemical structure that is in fact “substantially similar” to that of a listed controlled substance. Id. at 1887–89. To the contrary, Dr. Erickson opined that the chemical structure of at least some of the compounds named in the indictment were dissimilar to the Schedule I controlled substances identified by the Government's experts. Id. at 1889–91.

On July 26, 2017, after hearing two weeks of evidence, the jury returned guilty verdicts against Raymond and Requena on both counts alleged in the first superseding indictment. Dkt. Nos. 198, 199. Thereafter, Judge Mordue sentenced Raymond principally to a total of 300 months’ imprisonment and Requena principally to a total of 240 months’ imprisonment. Dkt. No. 294.

Both defendants took a direct appeal. Dkt. Nos. 297, 300. But a panel of the Second Circuit affirmed their convictions and sentences on November 4, 2020, United States v. Requena, 980 F.3d 30 (2d Cir. 2020), and the U.S. Supreme Court denied their petition for a writ of certiorari on June 14, 2021, Raymond v. United States, ––– U.S. ––––, 141 S. Ct. 2761, 210 L.Ed.2d 908 (2021) (Mem.). Defendants filed these separate counseled § 2255 motions on June 10, 2022. Dkt. Nos. 356, 357.

III. LEGAL STANDARD

Congress enacted § 2255 in 1948 to alleviate a practical problem: federal courts in certain judicial districts were getting swamped with habeas corpus petitions. United States v. Hayman, 342 U.S. 205, 213–14, 72 S.Ct. 263, 96 L.Ed. 232 (1952). This was something of a self-inflicted judicial injury. The Supreme Court had been aggressively expanding the habeas corpus remedy, which meant that a growing number of prisoners were filing post-conviction petitions. Id.

Because the traditional writ of habeas corpus acts against the prisoner's warden, federal courts in the small number of judicial districts where federal prisons were located soon became overwhelmed. Hayman, 342 U.S. at 214 & n.18, 72 S.Ct. 263. So Congress created a broad, habeas-type statutory remedy that would spread out this seemingly ever-growing workload by returning jurisdiction over challenges to federal convictions to the sentencing court. United States v. Addonizio, 442 U.S. 178, 185, 99 S.Ct. 2235, 60 L.Ed.2d 805 (1979).

Section 2255 provides that a “prisoner in custody under sentence of a [federal] court ․ claiming the right to be released ․ may move the court which imposed the sentence to vacate, set aside or correct the sentence.” But the statute does not operate as a substitute for a direct appeal. United States v. Frady, 456 U.S. 152, 165, 102 S.Ct. 1584, 71 L.Ed.2d 816 (1982). Indeed, the kind of legal or factual errors that might warrant relief on a direct appeal are ordinarily not sufficient to justify collateral relief under § 2255. Addonizio, 442 U.S. at 184, 99 S.Ct. 2235.

Instead, the statute strikes a balance between the value of error-correction and the need for finality in criminal cases. United States v. Bokun, 73 F.3d 8, 12 (2d Cir. 1995). Thus, § 2255 relief is available “only for a constitutional error, a lack of jurisdiction in the sentencing court, or an error of law or fact that constitutes ‘a fundamental defect which inherently results in a complete miscarriage of justice.’ ” Id. (quoting Hill v. United States, 368 U.S. 424, 428, 82 S.Ct. 468, 7 L.Ed.2d 417 (1962)).

A sentencing court presented with a § 2255 motion must follow the Rules Governing § 2255 Proceedings for the United States District Courts. Under those Rules, the court can decide meritless claims on the basis of the papers, with or without a response from the Government. Rule 4(b); Rule 7(a). If a claim requires factual development, the court can order discovery or expand the paper record. Rule 6; Rule 7. Thereafter, the court is expected to hold an evidentiary hearing “unless the motion and the files and records of the case conclusively show that the prisoner is entitled to no relief.” § 2255(b). As the Second Circuit has explained:

The procedure for determining whether a hearing is necessary is in part analogous to, but in part different from, a summary judgment proceeding. The petitioner's motion sets forth his or her legal and factual claims, accompanied by relevant exhibits: e.g., an affidavit from the petitioner or others asserting relevant facts within their personal knowledge and/or identifying other sources of relevant evidence. The district court reviews those materials and relevant portions of the record in the underlying criminal proceeding. The court then determines whether, viewing the evidentiary proffers, where credible, and record in the light most favorable to the petition, the petitioner, who has the burden, may be able to establish at a hearing a prima facie case for relief. If material facts are in dispute, a hearing should usually be held, and relevant findings of fact made.

Puglisi v. United States, 586 F.3d 209, 213 (2d Cir. 2009) (cleaned up).

IV. DISCUSSION

Raymond and Requena each argue that their former trial attorneys; i.e., Attorney Marks and Attorney McBride, failed to adequately prepare for the technical aspects of the trial, particularly with regard to the expert witness testimony. In addition, Raymond argues that Attorney Brooklier (the man who led Raymond's defense team until his unexpected death) gave him bad advice during the plea-bargaining stage.

The Sixth Amendment guarantees a criminal defendant the right to effective assistance from his attorney. Gonzalez v. United States, 722 F.3d 118, 130 (2d Cir. 2013). To prove ineffective assistance, a petitioner must show that (1) “counsel's representation fell below an objective standard of reasonableness” and that (2) “there is a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different.” Strickland v. Washington, 466 U.S. 668, 688, 694, 104 S.Ct. 2052, 80 L.Ed.2d 674 (1984).

Under the first prong of Strickland, courts apply a “strong presumption that counsel's conduct falls within the wide range of reasonable professional assistance.” 466 U.S. at 689, 104 S.Ct. 2052. To overcome this presumption, the petitioner bears the burden of showing “that counsel's representation was unreasonable under prevailing professional norms and that the challenged action was not sound strategy.” Kimmelman v. Morrison, 477 U.S. 365, 381, 106 S.Ct. 2574, 91 L.Ed.2d 305 (1986).

Under the second prong of Strickland, a petitioner must “affirmatively prove prejudice” by showing that “there is a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different.” 466 U.S. at 693–94, 104 S.Ct. 2052. A reasonable probability is defined as “a probability sufficient to undermine confidence in the outcome.” Id. at 694, 104 S.Ct. 2052.

A. Attorney Brooklier

Raymond argues that Attorney Brooklier (who led Raymond's team of lawyers until his unexpected death) misadvised him about two issues during the plea-bargaining stage. Dkt. No. 357-2 at 11–17.⁷

First, Raymond claims that he rejected the Government's fourteen-year plea offer because Attorney Brooklier mistakenly told him that the jury would have to make a unanimous finding about which of the six chemical compounds named in the first superseding indictment were “substantially similar” to the controlled substances listed on Schedule I. Dkt. No. 357-2 at 12 (emphasis added). Second, Raymond argues that Attorney Brooklier misadvised him about the statutory maximum penalties he would face if he took the case to trial. Id. at 14. According to Raymond, the Court should vacate [his] 25-year sentence and compel the Government to re-offer the same plea deal for [him] to accept now (with credit for time served).” Id. at 17.

1. Juror Unanimity

First, Raymond argues that Attorney Brooklier misstated the law when he advised him that the jury would be required to decide unanimously which of the chemical compounds named in the first superseding indictment qualified as a controlled substance analogue.

As relevant here, Raymond avers in his supporting affidavit that Attorney Brooklier “explained to [him] that a jury must decide unanimously which substance listed in the [first superseding indictment] qualified as a controlled substance analogue” and “told [him they] needed ‘one juror to agree with [them] that a substance is not an analogue’ while the government ‘needs all 12.’ ” Raymond Aff., Dkt. No. 357-3 ¶¶ 7–8.

Although Raymond acknowledges that Attorney Brooklier advised him to accept the Government's plea offer rather than go to trial, Raymond insists that he “rejected the plea offer because [he] believed, based on Mr. Brooklier's advice, the government would not be able to prove beyond a reasonable doubt to a unanimous jury that any single substance listed in the indictment was a controlled substance analogue.” Raymond Aff. ¶ 9.

The Sixth Amendment right to effective assistance of counsel extends to the plea-bargaining process. Lafler v. Cooper, 566 U.S. 156, 162, 132 S.Ct. 1376, 182 L.Ed.2d 398 (2012). “To provide constitutionally adequate representation during plea negotiations, a lawyer must generally advise the client of any offer that the government extends, outline the strengths and weaknesses of the case against him, and provide an estimate of the defendant's sentencing exposure at trial.” Siraj v. United States, 999 F. Supp. 2d 367, 370 (E.D.N.Y. 2013) (cleaned up).

Upon review, Attorney Brooklier's advice about jury unanimity under the Analogue Act does not amount to a plausible claim of ineffective assistance that might warrant further proceedings on an expanded record.⁸ To be sure, Raymond is correct that a lawyer's advice to a client during plea negotiations is constitutionally deficient when it is “contrary to the applicable law.” Dkt. No. 357-2 at 12 (emphasis added).

The problem for Raymond is that Attorney Brooklier's legal advice on this unanimity issue was not contrary to the then-applicable law in the Second Circuit. Instead, as Raymond concedes, the question of whether a unanimous jury finding was required was still a so-called “open question” in the Second Circuit at the time of his prosecution. Raymond Aff. ¶ 10.

Unfortunately for Raymond, the Second Circuit finally elected to resolve this “open question” in connection with his direct appeal. There, apparently for the first time, the appeals court held in a published opinion that “a substance's analogue status is nothing more than a means of fulfilling the element that the defendant's conduct involved a ‘controlled substance’ ” and, that therefore, a jury “need not unanimously agree on any more specific description of that substance.” Requena, 980 F.3d at 50–51.

In other words, Attorney Brooklier's advice about jury unanimity was not “incorrect” at the time it was rendered. Instead, it was a legal opinion about the application of an unsettled issue. In fact, even after Attorney Brooklier's death, other members of Raymond's defense team still elected to propose a jury instruction on unanimity. See Dkt. No. 169. Ultimately, Judge Mordue rejected that proposal and instead charged the jury in relevant part that:

Now in order to convict a defendant on Count 1, you must unanimously agree that the government has proven that at least one of the substances identified in Count 1 of the indictment qualifies as a controlled substance analogue. You need not, however, unanimously agree on which of the substance or substances qualify as a controlled substance analogue.

Tr. at 2107–08 (emphasis added).

Importantly, though, because “[w]e evaluate ineffective assistance of counsel using a freeze frame—when the alleged poor performance occurred, not sometime later when the law finally gets settled,” Deck v. Jennings, 978 F.3d 578, 583 (8th Cir. 2020), the fact that Attorney Brooklier's legal opinion on juror unanimity turned out to be wrong does not itself render his advice during the plea-bargaining stage constitutionally deficient. See, e.g., Smith v. Singletary, 170 F.3d 1051, 1054 (11th Cir. 1999) (“The giving of legal advice that later is proven to be incorrect ․ does not necessarily fall below the objective standard of reasonableness.”).

Instead, the relevant question is whether Attorney Brooklier's legal advice on this topic was unreasonable based on the state of the law at the time. See, e.g., Cisneros v. United States, 2020 WL 9934484, at *16 (S.D. Tex. Sept. 23, 2020) (holding counsel “cannot be found to be ineffective for giving [his client] a reasoned legal opinion of how the Court would resolve an unsettled legal issue”). After all, a constitutionally adequate attorney must “be a reasonably competent legal historian.” Cooks v. United States, 461 F.2d 530, 533 (5th Cir. 1972). “Though he need not see into the future, he must reasonably recall (or at least research) the past.” Id.

The parties seem to agree that this jury unanimity issue was not resolved in connection with the Analogue Act until after Raymond and Requena were convicted. With that in mind, it might have been possible to formulate an argument that pulls together contemporary lower court precedent from at or around the time of Attorney Brooklier's allegedly bad advice to show how it might have been unreasonable at the time it was rendered.

But Raymond has not developed any such argument. Instead, Raymond's only argument on this point is that Attorney Brooklier's advice was deficient within the meaning of Strickland because it turned out to be wrong on an unsettled issue of law. Taken as true, that is not constitutionally deficient attorney performance. Accordingly, this argument will be rejected.

2. Statutory Maximum Penalties

Second, Raymond argues that Attorney Brooklier failed to correctly advise him about the statutory maximum penalties he would actually face if he took the case to a trial. According to him, Attorney Brooklier “did not correct the government's assertion in its February 26, 2016, email that if Mr. Raymond were found guilty at trial, he would face more than the ‘statutory maximum’ of ‘20 years.’ ” Dkt. No. 357-2 at 14.

On February 26, 2016, during plea negotiations, the Government sent to Raymond's defense team an e-mail in which she explained that “there is no statutory mandatory minimum” in play; that any sentence would be “driven by the advisory guidelines”; and that, based on an “extremely conservative estimate” of drug weights that did not account for the weight of additional compounds that also very likely applied, there was some “good news”: “if convicted, the defendants will only be facing 20 years.” Ex. D, Dkt. No. 357-6 (emphasis added).

Several weeks later, on March 21, 2016, Attorney Brooklier sent Raymond a letter in which he cautioned his client that “I speak for your defense team when I tell you that we consider the likelihood for success in this case as being extremely slim.” Ex. E, Dkt. No. 357-7. There, Attorney Brooklier also explained that, if plea negotiations fell apart, the Government would be likely to add substantial drug weights, and possibly even more charges, that “will vastly increase” his sentencing exposure. Id.

Further, Attorney Brooklier explained, if Raymond were convicted at trial the impact of certain sentencing guidelines adjustments would permit Judge Mordue to impose a sentence that would “most likely far exceed the 20 year statutory maximum” on Count One. Ex. E. Accordingly, Attorney Brooklier cautioned Raymond that “proceeding in this matter would very likely subject you to a potential sentence of several decades in custody.” Id. (emphasis added).

Upon review, Raymond has not plausibly established any constitutionally deficient performance in connection with this exchange. First, to the extent that Raymond's § 2255 claim is based on his assertion that the Government's letter might have been confusing or misleading to him, he has not identified any legal authority that would support a grant of habeas relief on that basis.

Second, even assuming the representations in the Government's February 26 letter were (a) sufficiently confusing or misleading; and (b) chargeable to Attorney Brooklier as a matter of Strickland and § 2255, it would not justify any further habeas inquiry. “Because counsel must avoid both failing to give advice and coercing a plea, counsel's conclusion as to how best to advise a client enjoys a wide range of reasonableness.” Fulton v. Graham, 802 F.3d 257, 265 (2d Cir. 2015) (cleaned up).

Attorney Brooklier's follow-up letter to Raymond fell well within this wide range of reasonable advice. There, Attorney Brooklier made it clear that the 240-month sentence forecasted by the Government was actually extremely conservative, failed to account for certain discretionary sentencing factors that would “most likely far exceed the 20 year statutory maximum” on Count One, and would almost certainly expose Raymond to “several decades” of prison time. “Several” is, by definition, more than two.

Third, as the Government points out, Raymond's supporting affidavit does not actually claim that this alleged confusion about his maximum sentencing exposure affected his decision to take the matter to trial (contrast this with his earlier claim about the jury unanimity issue, where he did claim that this alleged confusion caused him to proceed to trial).⁹ See Ex. A, Dkt. No. 357-3.

Fourth, in addition to Attorney Brooklier's March 21 letter, Raymond also received further explanation and warnings about the serious nature of his sentencing exposure from Attorney Marks, who took over the defense after Attorney Brooklier's unexpected death. Ex. 1, Dkt. No. 386-1 ¶¶ 20–21. In his affidavit, Attorney Marks avers that he “never informed [Raymond] that 20 years was the maximum sentence”; instead, he specifically remember[s] telling [him] that he would likely go to prison for most of the rest of his life” if he did not take a plea deal. Id.

In sum, Raymond has not plausibly identified constitutionally deficient performance that might be attributed to Attorney Brooklier in connection with the plea-bargaining process. Accordingly, his arguments about Attorney Brooklier will be rejected.

B. Attorney Marks & Attorney McBride

Next, Raymond and Requena argue that their former trial attorneys (i.e., Attorney Marks for Raymond and Attorney McBride for Requena) failed to adequately prepare and mount an expert defense at the trial. As defendants explain, the Analogue Act is a very technical, fact-intensive law—the statute requires the jury to determine “[w]hether a substance's chemical structure is sufficiently similar to the chemical structure of a controlled substance to be considered an analog.” United States v. Long, 15 F. Supp. 3d 936, 939 (D.S.D. 2014).

Importantly, however, because this “substantial similarity” requirement does not have a generally accepted scientific definition, see United States v. Makkar, 810 F.3d 1139, 1143 (10th Cir. 2015), Analogue Act prosecutions “inevitably involve[ ] a degree of uncertainty,” United States v. Demott, 906 F.3d 231, 237 (2d Cir. 2018). Accordingly, these cases typically boil down to a “battle of the experts,” in which the Government and the defense put on competing scientific experts to try to persuade the jury to adopt opposing views of the technical proof. See, e.g., United States v. Forbes, 806 F. Supp. 232, 238 (D. Colo. 1992).

1. Battle of the Experts

Defendants argue that their attorneys failed to adequately prepare for this “battle of the experts.” Raymond, for his part, argues that “[t]he trial record and the exhibits attached to [his] motion to vacate establish that [Attorney Marks's] representation was unconstitutionally ineffective because he did not adequately prepare for trial with [ ] Raymond's expert witnesses.” Dkt. No. 357-2 at 17–18. Likewise, Requena argues that Attorney McBride failed to adequately prepare for trial by failing to retain separate experts in chemistry or pharmacology. Dkt. No. 356-2 at 11–12. According to Requena, disputes with Attorney McBride over expenses and payment led his counsel to skip out on the due diligence that this complex prosecution demanded. Id. at 12–15.

To provide constitutionally adequate representation, “counsel has a duty to make reasonable investigations or to make a reasonable decision that makes particular investigations unnecessary.” Lindstadt v. Keane, 239 F.3d 191, 200 (2d Cir. 2001) (quoting Strickland, 466 U.S. at 691, 104 S.Ct. 2052); United States v. Tucker, 716 F.2d 576, 581 (9th Cir. 1983) (“Pretrial investigation and preparation are the keys to effective representation of counsel.”).

Importantly, however, this duty to investigate does not “compel defense counsel to investigate comprehensively every lead or possible defense or to scour the globe on the off-chance something will turn up.” Greiner v. Wells, 417 F.3d 305, 321 (2d Cir. 2005) (cleaned up). Instead, “[t]he reasonableness of an investigation is obviously a reflection of the facts of a case.” Id.

Defendants’ expert-preparation arguments are based in substantial part on affidavits from Dr. Erickson and Dr. DeCaprio, the expert witnesses they used at trial. In both affidavits, these former witnesses opine that neither Attorney Marks nor Attorney McBride “meaningfully engage[d]” with them in preparation for the trial. Dkt. Nos. 356-4, 356-5, 357-4, 357-5. In response, the Government has offered declarations from Attorney Marks and Attorney McBride. Dkt. No. 386-1 (Marks); 386-24 (McBride).

Because the question of whether one or both defendants might have raised a plausible claim of ineffective assistance on this basis involves a careful review of these filings, the parties’ offerings are worth recounting at length.

a. Raymond's Filings

Raymond has offered an affidavit from Dr. Erickson. There, Dr. Erickson avers that Attorney Brooklier hired him in July of 2015 “to assess whether certain synthetic cannabinoids qualified as controlled substance analogues because the synthetic cannabinoid was substantially similar in chemical structure to a controlled substance.” Erickson Aff., Dkt. No. 356-4 ¶ 2. As Dr. Erickson explains, he believes that these Analogue Act prosecutions “are especially challenging because the chemistry and pharmacology involved go well beyond the training of most attorneys.” Id. ¶ 4.

On July 29 through August 2, 2015, Dr. Erickson met with Raymond and Attorney Brooklier, Attorney Marks, and another member of their defense team in Los Angeles, California. Erickson Aff. ¶ 5. These meetings took up “about eight hours over the course of three days.” Id. There, Dr. Erickson “explained to [Raymond's] counsel the unique scientific challenges posed in Analogue Act prosecutions.” Id. In Dr. Erickson's view, Attorney Brooklier “was not experienced in defense of Analogue Act prosecutions or other similar cases.” Id. at ¶ 6.

Thereafter, Dr. Erickson avers that he had “four conference calls with Mr. Raymond's counsel on January 15, 2016, January 22, 2016, January 29, 2016, and February 22, 2016.” Erickson Aff. ¶ 7. Dr. Erickson states that he also met briefly with Attorney Brooklier on March 17, 2016, when Brooklier and Raymond came to Syracuse, New York for a “reverse proffer” session with the United States Attorney's Office. Id. ¶ 8.

Later, Dr. Erickson spoke with Attorney Marks for “less than an hour” on April 7, 2017. Erickson Aff. ¶ 9. Dr. Erickson states that he had three more calls with Attorney Marks on April 21, 2017, June 8, 2017, and July 5, 2017. Id. ¶ 10. According to Dr. Erickson, these calls “were mostly about the case status and other Analogue Act prosecutions.” Id.

Dr. Erickson states that he does not “recall any serious discussion of chemistry during those three additional calls” and could not recall “discussing in detail” with Attorney Marks the reports he had prepared. Erickson Aff. ¶¶ 10–11. Dr. Erickson states that he also “prepared questions for Mr. Marks to assist him with his cross-examination of” the Government's expert chemist, Dr. Van Linn. Id. ¶ 11.

Dr. Erickson further avers that he testified at Raymond's trial on July 21, 2017. Erickson Aff. ¶ 12. But Dr. Erickson does not offer any details about his testimony at trial or the questions that Attorney Marks did or did not ask of him. See id. Instead, in his affidavit Dr. Erickson offers his “opinion” that Attorney Marks “failed to meaningfully engage with me in preparation for trial.” Id. ¶ 13. In Dr. Erickson's view, Attorney Marks failed to “ask for my assistance with understanding the chemistry involved in my testimony or a proposed cross.” Id. According to Dr. Erickson, Attorney Marks “should have devoted additional time and resources to better understand the subject matter that was the crux of [Raymond's] ․ prosecution.” Id.

Raymond has offered a similar affidavit from Dr. DeCaprio. There, Dr. DeCaprio avers that Raymond's defense attorneys hired him on April 4, 2016, “to assess whether certain synthetic cannabinoids qualified as controlled substance analogues because the synthetic cannabinoid was substantially similar in pharmacological effect to a controlled substance.” DeCaprio Aff., Dkt. No. 357-5 ¶ 2. Like Dr. Erickson, Dr. DeCaprio believes that “Analogue Act prosecutions are very complex” and that “attorneys defending such cases require guidance and assistance from scientific experts to effectively prepare for trial.” Id. ¶ 4.

Dr. DeCaprio avers that he “spent the first year of [his] engagement speaking” directly with Raymond instead of the attorneys on his defense team. DeCaprio Aff.¶ 4. In Dr. DeCaprio's view, this was “unlike” any of the other cases on which he had consulted. Id. ¶ 6. However, after Dr. DeCaprio “express[ed] [his] concern about the performance of [Raymond's] counsel,” he had two conference calls with Raymond's attorneys on June 28, 2017 and July 5, 2017. Id. ¶¶ 6–7.

Dr. DeCaprio does not “recall having any further calls or meetings with” Raymond's counsel. DeCaprio Aff. ¶ 7. During the trial, Dr. DeCaprio recalls that he “spent about 20 minutes” with Attorney Marks to prepare for his own testimony, id. ¶ 8, and that he prepared some questions for Attorney Marks to assist him in the cross-examination of Dr. Trecki, the Government's expert pharmacologist, id. ¶ 9.

Dr. DeCaprio further avers that he testified at Raymond's trial on July 21, 2017. DeCaprio Aff. ¶ 10. But Dr. DeCaprio does not offer any allegations about Attorney Marks's direct examination of him at trial, nor does he offer any critique of Attorney Marks's cross-examination of Dr. Trecki. Instead, Dr. DeCaprio claims that Attorney Marks did not “meaningfully engage with [him] in preparation for trial.” Id. ¶ 11. According to Dr. DeCaprio, Attorney Marks “should have devoted additional time and resources” to help him “to better understand the subject matter” and to better “prepare for the direct examinations and cross-examinations of expert witnesses.” Id.

The Government, for its part, has offered a declaration from Attorney Marks. Marks Decl., Dkt. No. 386-1. There, Attorney Marks explains that he took over the role of lead counsel after Attorney Brooklier's death. Id. ¶¶ 4–5. According to Attorney Marks, because of the “small size of [the law firm] and the nature of [his] law partnership, he “was aware of and directly involved in the representation of [Raymond] even before” Brooklier's unexpected death. Id. ¶ 5. For instance, Attorney Marks asserts that he “attended meetings” with Raymond and Brooklier “in which we discussed factual and legal issues,” and “was generally familiar with the facts and the relevant law pertaining to the case.” Id.

Attorneys Marks further avers that he attended some meetings with Dr. Erickson over several days “and was able to meet, speak with, and ask questions.” Marks Decl. ¶ 6. Attorney Marks asserts that he spoke with Dr. Erickson and “frequently received emails from him related to the case.” Id. According to Attorney Marks, although he was not initially lead counsel, he still “looked at discovery material and had many lengthy discussions with [Attorney] Brooklier about the evidence and the trial strategy.” Id. ¶ 7. Attorney Marks also asserts that he was already “familiar with the file and with [Raymond] and Dr. Erickson” when Attorney Brooklier died. Id.

After Attorney Brooklier's death, Attorney Marks avers that he “began spending more time on the case.” Marks Decl. ¶ 7. For instance, another member of the defense team, an attorney named Darren Kavinoky “became less involved as trial approached.” Id. ¶ 8. Although Mr. Kavinoky helped in various areas in preparing for trial, “it was not anticipated that he would be at counsel table during the trial.” Id. Instead, an attorney named Pamela Tower became part of the trial team and worked “to assist with legal research and writing and” served as “the second-chair attorney at trial.” Id.

Attorney Marks avers that, throughout the course of his representation of Raymond, he “found him to be an extremely intelligent individual.” Marks Decl. ¶ 9. As Attorney Marks explains, Raymond had “years of experience” in this area of science and chemistry and had done his own, extensive research that caused him to be “uniquely well informed about and had a firm grasp of the chemical makeup of the various substances at issue in the case and of other issues relating to the expert testimony.” Id.

For instance, Attorney Marks avers that “[i]t was important” to Raymond “to be in direct contact with Dr. Erickson and, later, with ․ [Dr.] DeCaprio,” too. Marks Decl. ¶ 9. Attorney Marks avers that Raymond “was frequently the first point of contact with the expert witnesses, and he frequently asked questions of them and passed along to me their answers.” Id. Attorney Marks states that he “also had multiple phone calls with the experts in preparation for trial in addition to ․ many frequent meetings, phone calls, and email exchanges with [ ] Raymond about expert-related issues.” Id.

As Attorney Marks explains, he “understood from the beginning of the case that any trial involving alleged controlled substance analogues would involve competing expert testimony that would be central to the issue of criminal liability.” Marks Decl. ¶ 10. According to Attorney Marks, he “read and analyzed voluminous documentation sent to me by the experts and by [ ] Raymond himself” and “became significantly more knowledgeable about the expert issues in the case.” Id. ¶¶ 10–11.

Further, because Raymond was on pre-trial release, Attorney Marks asserts that “he would often spend two or three days a week” at Attorney Marks's “office discussing the case and reviewing factual and legal issues with [him].” Marks Decl. ¶ 11. According to Attorney Marks, “[h]e and I were very focused on the expert issues and had many hours of discussions about issues relating to the defense expert and the Government's experts.” Id.

Attorney Marks asserts that he “spent hundreds of hours preparing for trial” and that Raymond “was aware of and consented to” his trial strategy, “including generally what [he] planned to present through the expert testimony of Dr. Erickson and Dr. DeCaprio.” Marks Decl. ¶ 12. According to Attorney Marks, he spent “many hours preparing for the direct examinations of these experts and was aided by materials they sent, including prior transcripts and court decisions” as well as “many hours preparing to cross-examine the Government's designated experts and had many lengthy and substantive conversations” with Raymond about these issues. Id.

Attorney Marks asserts that he exchanged “many, many” e-mails with Dr. Erickson that contained substantive information about his anticipated testimony. Marks Decl. ¶ 14. For instance, on July 20, 2017, Dr. Erickson sent to Attorney Marks a PowerPoint presentation—this sixth iteration of this document—that he planned to use in court the next day. Id. Likewise, Dr. Erickson also sent to Attorney Marks “draft versions of the questions he wanted me to ask him at trial.” Id. Attorney Marks claims that he “reviewed and considered all of this material” and discussed with Raymond his general plan for trial. Id. According to Attorney Marks, he and Raymond “were both generally in agreement with the approach Dr. Erickson recommended that [Attorney Marks] take with respect to his testimony.” Id.

Attorney Marks asserts that he also spent considerable time with the material that Dr. DeCaprio sent to help him “prepare to address the pharmacological effects of the substances at issue.” Marks Decl. ¶ 15. This material included proposed questions for direct examination as well as cross-examination questions for the Government's competing expert. Id. In addition, Attorney Marks notes that he received from Raymond an outline of Dr. DeCaprio's anticipated testimony. Id.

Attorney Marks denies that he did not engage with the materials sent him by Dr. Erickson and/or Dr. DeCaprio and denies that he somehow failed to adequately prepare for trial. Marks Decl. ¶ 16. Further, according to Attorney Marks, “[a]t no time did anyone associated with the trial—including Dr. Erickson, Dr. DeCaprio, or [ ] Raymond—ever suggest that I was not sufficiently knowledgeable about the expert issues or that I was not adequately prepared for trial.” Id.

To the contrary, Attorney Marks claims that he had a “cordial working relationship” with these experts, “and even during our final pretrial preparations neither of the experts expressed to me any reservations about my preparation, strategy, or the substance of my anticipated questions, which we communicated about in advance of testifying.” Marks Decl. ¶ 16.

Finally, Attorney Marks avers that he was aware that expert witnesses for defendants in Analogue Act prosecutions—including Dr. Erickson and Dr. DeCaprio—had not had very much success in convincing juries that designer substances were not unlawful analogues. Marks Decl. ¶ 18. According to Attorney Marks, this “poor track record” and his own understanding of the “uphill battle faced by the defense” is the reason he “spent so much time preparing and attempting to streamline [his] points and arguments in a way that the jury could understand and follow and that would be persuasive.” Id.

Upon review of these filings, the record does not reveal any plausible claim of ineffective assistance of counsel that might warrant further proceedings on an expanded record. To be sure, a counsel's failure to adequately prepare for trial can constitute constitutionally deficient representation. But Raymond's filings do not establish anything even approaching constitutionally deficient expert preparation by Attorney Marks.

For instance, Raymond argues that Attorney Marks failed to adequately prepare for the expert testimony because he did not spend enough time with the expert witnesses and did not develop a sufficient understanding of their conclusions and their proposed testimony. But the available record indicates that Attorney Marks spent time conferencing with both experts, obtained their reports, and studied them in preparation for trial. Notably, neither expert contends that Attorney Marks failed to meet with them or failed to engage with them in preparation for trial. Instead, the experts merely opine that Attorney Marks should have spent more time with them.

That kind of subjective, conclusory value judgment is hardly enough to trigger a more expansive inquiry. Walters v. United States, 2022 WL 890906, at *5 (S.D.N.Y. Mar. 25, 2022) (“Counsel's alleged failure to more exactingly prepare or supervise an otherwise competent expert does not fall outside the wide range of professionally competent assistance to which [defendant] was entitled.”).

Importantly, nothing in either expert affidavit: (1) indicates that Attorney Marks labored under any particular misunderstanding about the scientific evidence; (2) identifies any necessary questions that Attorney Marks might have failed to ask on direct examination; or (3) points out any specific errors Attorney Marks might have made in putting on their expert opinions.

Nor is there anything in the available record, including this Court's own review of the trial transcript, that indicates that Attorney Marks made some specific error, or combination of errors, in connection with this preparation. Accordingly, Raymond's arguments about trial preparation will be rejected.

b. Requena's Filings

Requena has offered an affidavit in which he avers that he hired Attorney McBride after being indicted on March 12, 2015. Requena Aff., Dkt. No. 356-3 ¶ 2. According to Requena, the engagement letter he signed with Attorney McBride “did not provide for the payment of fees, or a budget, to retain an expert witness as part of [his] defense.” Id. ¶ 2. Requena avers that, after the indictment was superseded, he signed an amended fee agreement with Attorney McBride. Id. ¶ 4. However, Requena does not discuss any of the terms of that agreement or provide any more information about the nature of his relationship with counsel. See id.

Instead, Requena has offered the same affidavit from Dr. Erickson that has already been discussed at length. Dkt. No. 356-4. As relevant here, Dr. Erickson avers that Requena did not retain him “directly,” but acknowledges that Attorney McBride was “present” for his meeting with Attorney Brooklier and was “present” with during his testimony at trial. Erickson Aff. ¶ 14.

Requena has also offered the same affidavit from Dr. DeCaprio that has already been discussed at length, too. Dkt. No. 356-5. As relevant here, Dr. DeCaprio avers that Requena did not retain him “directly” and does not recall “preparing for trial” with Attorney McBride, but acknowledges that Attorney McBride was “present” with Raymond and Attorney Marks during his expert testimony at trial. DeCaprio Aff. ¶ 12.

Requena has also offered a series of e-mails he exchanged with Attorney McBride in advance of trial. Ex. D, Dkt. No. 356-6. For instance, in an e-mail dated September 8, 2016, Requena noted that Attorney McBride had mentioned trying to meet with Raymond's counsel to discuss “meeting with the chemist and how we can being to put together our defense[.]” Id. at 3.

The next day, Attorney McBride responded that Raymond's counsel “has been hard to reach. Very hard.” Ex. D at 3. However, Attorney McBride told Requena that he and Raymond's counsel were scheduled to speak later that evening. Id. In closing, Attorney McBride promised to update Requena the next morning. Id.

The next e-mail offered by Requena is dated March 2, 2016. Ex. D at 5. In this e-mail, Attorney McBride explains to Requena that a certain Supreme Court case “is the law which the jury is given in deciding your case.” Id. As Attorney McBride's letter explained, a conviction required proof of “two things: (1) that, in your case, for example, you knew that, say, AB PINACA could be a controlled substance; and (2) that it was substantially similar—an analogue to—a controlled substance.” Id. Attorney McBride explained that, in his view, the prosecution's case against Requena would “come down to point two: ‘substantially similar’.” Id. Thus, the trial would be “a battle of the experts.” Id.

Attorney McBride further explained to Requena that “[w]e are having a significant amount of trouble finding an expert who will say that AB PINACANA is not substantially similar. They have experts on this topic who will most assuredly say it was an analog.” Ex. D at 5 (emphases in original). Attorney McBride suggested to Requena that he should read the attached case. Id. He further promised to be “in touch” about “going out to New York just as soon as I find out anything.” Id.

The third e-mail offered by Requena is also dated March 3, 2016. There, Attorney McBride e-mailed Requena and stated: “[a]s we discussed Monday, please do your best to get expert witness fees together.” Ex. D at 7. Attorney McBride had discussed the matter with Raymond's counsel, and “passed on” information to Requena that “the expert fees for this case, putting aside more legal fees in the event she returns a new indictment with the tax charges (which would be the first superseding indictment—i.e. ‘superseding’ the current straight indictment) could be anywhere from 30-60k. You and Drew [Raymond] would be splitting this.” Id. Attorney McBride explained that this money “would not be touched by us. This would be in our trust accounts, with anything left over of course going back to you guys.” Id.

The next e-mail offered by Requena is dated March 14, 2016. That day, Attorney McBride forwarded Requena an ECF notice in which the Court set some additional conditions for pre-trial release. Ex. D at 9. At that time, Attorney McBride asked Requena to “kindly advise on expert witness fees” because they “are meeting with one of [the] experts” in a few days. Id.

Attorney McBride e-mailed Requena again on May 31, 2016 to ask about the expert fees. Ex. D at 12. At that time, Attorney McBride reminded Requena that he'd promised Raymond's attorneys to help them with the expert fees on this case. Id. Attorney McBride states that: “I know money doesn't grow on trees—but having said that, do you know when you can pay the rest [of the fee]? In terms of at least decent concrete dates?” Id.

Requena replied to Attorney McBride later that day. Ex. D at 14. At that time, Requena told Attorney McBride: “I don't have concrete dates but I'm doing everything in my control to generate money to the point where I'm searching for a job to where my mom is assisting in refinancing to pull equity out of her property.” Id. Requena also asked Attorney McBride “when are we going to work on the details of the case.” Id. According to Requena, he was “lost with little information on strategy” and only knew about “one meeting with an expert” in Syracuse. Id. In response, Attorney McBride stated “Let's get to work then. What's [your] schedule in June?” Id. Requena responded to that by stating: “Ok. Let's talk about getting together next week. Will call you tomorrow.” Id. at 17.

Additional e-mails show that Attorney McBride kept Requena informed about filings being made in the case. For instance, on June 8, 2016, Attorney McBride sent Requena a copy of the motion to dismiss that he had filed. Ex. D at 20. At that time, Attorney McBride suggested meeting up the next day. Id. A few weeks later, on June 28, 2016, Attorney McBride e-mailed Requena about another meeting the next day and noted that “[t]here's much work to be done.” Id. at 22. At that time, Attorney McBride stated that “[w]e start basically a life trial in three months” and, as a result of the high stakes, he was “concerned about funds, and this is apart from the fact that I'd like to contribute, in good faith and to strengthen the cohesiveness, of the defense team re: our expensive experts.” Id.

The next e-mail exchange is from October 14th and 15th, 2016. Ex. D at 24–25. First, Requena e-mailed Attorney McBride to “voice concerns” he had about the handling of his case. Id. at 24. For example, Requena stated that he doubted Attorney McBride had put in a sufficient amount of effort on the matter and “wanted to find out if the key reason for not putting in the effort needed is because of my current inability to raise the funds to pay the remaining balance?” Id. Requena also noted that Attorney McBride had sent him a text message on May 17, 2016, expressing a need for the two to meet and go through the discovery the government had produced. Id. However, Requena noted that they had not yet met to do so. Id. According to Requena, he and Attorney McBride had only met twice in recent months. Id.

Attorney McBride e-mailed a few hours later and stated that he had just tried to call and text Requena. Ex. D at 27. At that time, Attorney McBride stated that he had “sent [Requena] every single document filed by the government” as well as a “briefing” that was “required reading in terms of giving you an overall structure of how your trial will go.” Id. Although they would certainly continue going over discovery, Attorney McBride cautioned Requena that “a great majority of [the Government's] case, if not all, will be the documents they showed you at the reverse proffer.” Id.

Requena and Attorney McBride exchanged more e-mails about motions in limine and trial strategy in October and November of 2016. Ex. D at 30–41. For instance, on November 1, 2016, Attorney McBride explained to Requena that motions needed to be filed by each defendant separately and agreed that a meeting to discuss shared strategy might be good. Id. Later, on December 14, 2016, Attorney McBride e-mailed Requena to let him know that Attorney Brooklier's death would delay the trial date. Ex. D at 44.

Later e-mail exchanges show that Requena became increasingly frustrated with these delays and with Attorney McBride. On April 16, 2017, Requena e-mailed Attorney McBride to unload his accumulated grievances. Ex. D at 50. There, Requena complained that:

Mark,

This will be my last attempt to communicate with you.

I do not understand why you have decided to ignore my phone calls, emails, and text messages asking for an update on my case.

There is 12 days left until all pre-trial motions are due and I am completely in the dark with where we are. The last time I had any communication with anyone with respects to my case was on February 17, 2017 exactly 58 days ago from the date of the email.

Mark, personally I do not understand what I have done to you to deserve the actions which you have displayed, business wise it is completely unprofessional; however, you once looked me in my face and told me “you cared,” believing your words is why I stuck with you and believed in you and now I feel as if you betrayed my trust. When I ran into financial hardships and was turned upside down financially I was upfront with you and wanted to make sure that if you wanted to continue to represent me, which you agreed to, therefore, I do not understand what the problem is, especially since you will not use any method available to communicate with me.

I am feeling discouraged and let down Mark, because it was you on June 29, 2016 that said we are “starting a life trial” and a lot of work needs to be done where you will not be taking any new cases. I still have yet to see what work has been done? Above and beyond that Mark, tell me if the roles were reversed how would you feel? Would your confidence in the individual that is to represent and fight for you tank like mine has? Or how about when you tell me that your going to get me the rest of the discovery, where back on October 20, 2016 your assistant was supposed to hand it off to me because you had to leave town that evening then telling me February 9, 2017 that you are copying the CD's and by Saturday you will be giving me copies. In all Mark I can go on and on with why I feel completely let down by your actions.

I would like to have a face to face meeting with you to discuss your actions with respect to my case and figure out what has been completed as to the strategies discussed February 9, 2017.

Ex. D at 50. Attorney McBride responded the next day, promising to call back and set up a meeting for later that week. Id. The record shows that Attorney McBride filed pre-trial motions on April 28, 2017. Dkt. No. 123.

The Government, for its part, has offered a responsive declaration from Attorney McBride. McBride Decl. Dkt. No. 386-24. There, Attorney McBride avers that “[f]rom the beginning of our association, [ ] Requena made it clear that he and [ ] Raymond were close friends and that they intended to coordinate their defense as much as possible.” Id. ¶ 5.

According to Attorney McBride, Raymond and Requena “agreed to hire one set of defense experts for trial, rather than to present separate sets of experts.” McBride Decl. ¶ 5. In Attorney McBride's view, this was a good strategic decision: “it was in the best interest of my client to present a unified defense on the expert front rather than risking hiring a separate set of experts who might have different opinions or bases for their opinions which could confuse the jury and provide prosecution with more opportunities to present their view of the evidence through cross-examination.” Id.

Attorney McBride avers that he believes Raymond and/or Attorney Marks paid the expert fees even though Requena “told [him] specifically that he would help cover the expert expenses.” McBride Decl. ¶ 6. According to Attorney McBride, he is not aware of any payments that Requena made “to offset the expert witness fees.” Id.

Attorney McBride acknowledges that Requena failed to pay in full the flat fee they negotiated for the representation. McBride Decl. ¶ 7. “Consistent with [his] professional responsibility obligations and ethical duties, however,” Attorney McBride did his “best to represent [Requena] at all pretrial stages and throughout the jury trial itself, regardless of the unpaid retainer fee.” Id.

Attorney McBride further avers that he “did not knowingly or purposefully avoid preparing for trial or otherwise cut corners in [his] defense of [ ] Requena because of our fee dispute (or for any other reason).” McBride Decl. ¶ 7. According to Attorney McBride, he would “frequently” call Requena on the phone in response to his e-mails. Id. Because they negotiated a flat fee, Attorney McBride states that he did not record billable hours. Id. ¶ 8. Even so, Attorney McBride states that he believes he dedicated “hundreds of hours” to preparing for trial. Id.

As for the expert witnesses, Attorney McBride avers that “Mr. Raymond and Mr. Marks took the lead in coordinating with the experts[.]” McBride Decl. ¶ 8. According to Attorney McBride, he “knew and understood that at trial Mr. Marks would do the principal direct examinations of the two defense experts.” Id. Therefore, his own examinations of those experts would be “more limited in scope[.]” Id. As Attorney McBride explains, his examination would instead “focus on a few key issues rather than attempting to re-state all the points Mr. Marks was going to make in his direct examinations.” Id.

In March of 2016, Attorney McBride asserts that he and Requena traveled to Syracuse. McBride Decl. ¶ 9. There, they met with the Government and had a “reverse proffer” session, where they reviewed the evidence that would be presented at trial. Id. According to Attorney McBride, Requena was not interested in a plea deal despite the strength of the evidence against him. Id.

During this trip, Attorney McBride also met with Dr. Erickson “to learn more about the chemical structures of various substances charged in the indictment and to prepare for trial.” McBride Decl. ¶ 10. Later that month, Attorney Marks and Attorney McBride received a draft of an affidavit from a professor of chemistry and biochemistry at Florida State University. Id. ¶ 11.

Attorney McBride reviewed this affidavit and concluded the defense could not call the expert as a witness. McBride Decl. ¶ 11. As Attorney McBride explains, this proposed expert opined that AB-PINACA, one of the analogues charged in the indictment, was substantially similar to a listed controlled substance. Id. Attorney McBride knew such an admission was “fatal to the defense.” Id. “Ultimately, the defendants did not use this individual at trial, even though defense expert [Dr.] Erickson had given this chemist his ‘highest recommendation.’ ” Id.

Thereafter, Attorney McBride prepared for trial by speaking to both of the defense experts, “review[ing] everything [he] received that was circulated by the experts (some of which was forwarded to [him] by Mr. Marks), including expert reports and summaries and other helpful scientific information that helped [him] get up to speed on issues relating to their testimony.” McBride Decl. ¶ 12.

By the time of trial, Attorney McBride “felt [he] understood the relevant issues of chemistry and pharmacology sufficient to elicit the testimony [he] wanted from the defense experts, cross-examine the Government's experts, and argue and explain the chemical structures and pharmacological effects of the various substances to the jury.” McBride Decl. ¶ 13. Attorney McBride notes that he maintained a good working relationship with Attorney Marks and the experts before trial. Id. ¶ 14.

Finally, Attorney McBride states that while the experts now claim that he was unprepared, neither witness expressed any concerns to him before trial or during trial. McBride Decl. ¶ 14. Instead, according to Attorney McBride, “the experts were always positive and optimistic about the case.” Id. In his view, “all the principal points they flagged and communicated in advance of trial came out during their testimony and cross-examination of the Government's experts.” Id.

Upon review of these filings, the record does not reveal any plausible claim of ineffective assistance of counsel that might warrant further proceedings on an expanded record. Requena's cherry-picked e-mails do not tend to establish any constitutionally deficient conduct by Attorney McBride. Although these e-mails reflect tension over payment of fees, the rest of the record evidence shows that defendants continued to work together to prepare the same two experts and to present a unified defense at trial. United States v. Griffin, 324 F.3d 330, 364 (5th Cir. 2003) (“A decision by co-defendants to proceed with a unified defense is one of trial strategy, and not a basis for an ineffective assistance claim.”).

This unified defense is the kind of strategy choice that, absent good reason to think otherwise, should be left to trial counsel. Harrington v. Richter, 562 U.S. 86, 107, 131 S.Ct. 770, 178 L.Ed.2d 624 (2011) (“Counsel was entitled to formulate a strategy that was reasonable at the time and to balance limited resources in accord with effective trial tactics and strategies.”); see also Eze v. Senkowski, 321 F.3d 110, 132 (2d Cir. 2003) (abrogated on other grounds) (refusing to second-guess counsel's decision not to call a particular witness where the strategy advance client's interests).

In reply, Requena tries to cast doubt on this obvious historical fact despite it being manifest in the record. According to Requena, the filings show that there is a “genuine issue of material fact” regarding whether or not Attorney McBride prepared for trial with the two experts and, relatedly, whether his decision-making was driven by financial concerns rather than valid tactical ones. Dkt. No. 391 at 14–15.

These arguments will be rejected. First, neither expert affirmatively avers that Attorney McBride failed to prepare with them; instead, each expert says he was “not retained directly” by Attorney McBride and “[does] not recall” preparing with him. Even taken as true, this would not establish a plausible claim for ineffectiveness because Attorney McBride undisputedly undertook other forms of preparatory conduct that were constitutionally adequate.

Further, in addition to what has been discussed, the most compelling bit of evidence demonstrating that Attorney McBride adequately prepared for the technical aspects of this trial might come from an e-mail exchange between Raymond, members of Raymond's defense team, Dr. Erickson, and Attorney McBride.

There, the attorneys were discussing a scientific report from a chemistry professor named Gregory Dudley, a possible expert witness who proposed to opine on the chemical structures of the compounds named in the indictment. Although Dr. Erickson responded to this e-mail by offering his opinion that Professor Dudley's analysis was “outstanding” and “quite persuasive,” Ex. 18, Dkt. No. 386-26, Attorney McBride disagreed forcefully: “I don't think, as we have been discussing, this guy can come close to our case. The concern I have is an obvious one: page 9 and then running into 10 where our hopes would be essentially dashed vis a vis AB-Pinaca and ADB-Pinaca.” Ex. 19, Dkt. No. 386-27.

Obvious, indeed. Professor Dudley's written report is fairly technical, but the reason for Attorney McBride's objection becomes clear if you take a closer look at it: Professor Dudley opined that “AB-PINACA,” one of the chemical compounds allegedly used in defendants’ operation, was “substantially similar” to “ADB-PINACA,” a DEA-listed controlled substance. Ex. 19A, Dkt. No. 386-28. In other words, despite being a “solo” practitioner rather than part of Raymond's more sophisticated legal defense team, Attorney McBride appropriately reviewed Professor Dudley's technical report (after having read it even more closely than Dr. Erickson) and understood that Professor Dudley would be harmful to his client's defense of the charges.

Notably, neither expert affidavit claims that Attorney McBride failed to ask them appropriate questions at trial or that he failed to understand the science at the core of the prosecution. Instead, both of these affidavits neglect to acknowledge the obvious: the trial transcript shows that Attorney McBride conducted a reasonable, focused direct examination of both experts. Indeed, nothing offered in this record undermines Attorney McBride's assertion that he adequately prepared for the trial by reading the expert reports and other materials circulated to him as part of the defense team. Cf. Lindstadt, 239 F.3d at 202 (finding counsel's conduct inadequate where he failed to consult an expert, conduct relevant research, or request copies of underlying studies). Accordingly, this argument will be rejected.

2. Cross-examination

Defendants go on to argue that their former attorneys failed to adequately cross-examine the Government's experts. Broadly speaking, each defendant argues that their respective counsel failed to engage in the minutiae of the scientific issues in favor of more general lines of cross-examination. Dkt. No. 356-2 at 15–16; Dkt. No. 357-2 at 20–21.

“[T]he conduct of examination and cross-examination is entrusted to the judgment of the lawyer, and an appellate court on a cold record should not second-guess such decisions unless there is no strategic or tactical justification for the course taken.” United States v. Luciano, 158 F.3d 655, 660 (2d Cir. 1998); see also Walters v. United States, 2022 WL 890906, at *3 (S.D.N.Y. Mar. 25, 2022) (“Typically encompassed within the ambit of trial counsel's strategic discretion is ‘whether to call any witnesses on behalf of the defendant, and if so which witnesses to call.’ ”). “How to cross-examine an expert witness and whether to obtain one's own expert are ‘paradigmatic’ strategic choices traditionally reserved to trial counsel.” Walters, 2022 WL 890906, at *3 (citing Hinton v. Alabama, 571 U.S. 263, 274–275, 134 S.Ct. 1081, 188 L.Ed.2d 1 (2014) (per curiam)).

a. Raymond's Filings

Raymond contends that Attorney Marks failed to properly cross-examine Dr. Vann Linn. Dkt. No. 357-2 at 20–21. According to Raymond, Attorney Marks “failed to use the bulk of the questions Dr. Erickson prepared for him in his cross-examination” and instead “focused on Dr. Van Linn's general definition of ‘substantially similar,’ and the dissent within the DEA” that related to only one of the six substances at issue. Id. at 20.

Upon review, Raymond's argument does not amount to a plausible claim of ineffective assistance of counsel. A review of the trial transcript shows that Attorney Marks cross-examined Dr. Van Linn by attempting to undermine his assertions that the chemical structures of the analogues in question were “substantially similar” to those of DEA-scheduled substances. In doing so, Attorney Marks identified potential bias arising from Dr. Van Linn's DEA employment and attempted to demonstrate to the jury that Dr. Van Linn's conclusions were arbitrary and unfair and, in one case, even disputed by one of his own colleagues at the DEA.

Attorney Marks's approach to cross-examination was not constitutionally deficient. As Attorney Marks explained in his declaration, this prosecution involved difficult scientific issues that might seem hopelessly complex to an ordinary juror. It was completely reasonable for Attorney Marks to avoid quibbling with the Government's chemistry expert over chemical minutiae (using Dr. Erickson's proposed questions) in favor of a strategy more likely to be digested by the average juror: a line of cross-examination that attempted to undermine Dr. Van Linn's credibility by showing his bias.

Absent some far more compelling showing by Raymond, a seasoned lawyer like Attorney Marks who has otherwise acted diligently is not required to defer to the trial strategy and questions proposed by a non-attorney, even an expert witness. Ogundipe v. United States, 1997 WL 470371, at *1 (E.D.N.Y. July 2, 1997) (“Counsel's decisions regarding the calling of witnesses and the extent to which witnesses are to be cross-examined should not be second-guessed and do not, as a general rule, provide a basis for an ineffective assistance claim.”). Accordingly, this argument will be rejected.

b. Requena's Filings

Requena also contends that Attorney McBride failed to properly cross-examine Dr. Vann Linn. Dkt. No. 356-2 at 15–16. According to Requena, Attorney McBride “failed to challenge Dr. Van Linn's underlying scientific opinions regarding the substantial similarity in chemical structure[s]” in favor of “a single topic—the subjectivity of the term ‘substantially similar’ under the Analogue Act.” Id. at 15.

Upon review, Requena's argument does not amount to a plausible claim of ineffective assistance of counsel, either. As with Raymond's counsel, a review of the trial transcript shows that Attorney McBride's cross-examination of Dr. Van Linn attempted to undermine the idea at the core of the Government's prosecution; i.e., that a credentialed expert could render a credible, objective opinion on the “substantial similarity” issue. This was a reasonable strategic choice: if the jury rejected that premise, the Government would be unable to prove an element of the crime. Accordingly, this argument will be rejected.

3. Closing Arguments

Finally, defendants argue that there is a “substantial likelihood” that the outcome of trial would have been different for each of them if their former trial lawyers had “focused on the weaknesses in the government's assertions of substantial similarity.” Dkt. No. 356-2 at 15; Dkt. No. 357-2 at 12.

The Supreme Court has held that the right to effective assistance extends to closing arguments. Yarborough v. Gentry, 540 U.S. 1, 5, 124 S.Ct. 1, 157 L.Ed.2d 1 (2003). Although “[c]losing arguments should sharpen and clarify the issues for resolution by the trier of fact,” the tactical choice of “which issues to sharpen and how best to clarify them are questions with many reasonable answers.” Id. (cleaned up). Accordingly, “[j]udicial review of a defense attorney's summation is [ ] highly deferential.” Id.

a. Raymond's filings

Raymond contends that Attorney Marks failed to adequately address the expert testimony in his closing. But this does not amount to a plausible claim of ineffective assistance of counsel. A review of the transcript shows that Attorney Marks addressed the expert opinions in an adequate fashion.

For instance, Attorney Marks explained to the jury that they would be required to find that a substance involved had “a chemical structure that's substantially similar to a schedule I or II controlled substance, and then has to have a pharmacological effect, depressant, stimulant, or hallucinogenic effect that's similar to a I or II schedule.” Trial Tr. at 2043. Attorney Marks also argued that only a qualified expert chemist could even testify to whether the substances in question qualified as analogues. Id. On that question, Attorney Marks argued that the Government “can't prove it's a controlled substance analogue, because of the testimony in this case.” Id. Thereafter, Attorney Marks walked the jury through various reasons to discredit the testimony of the Government's expert witnesses, id. at 2043–2045 (Van Linn), 2046–2047 (Trecki), and described reasons to credit the defense's expert witnesses instead, id. at 2047–2048.

In short, Raymond's brief misstates the record by claiming that Attorney Marks made only a “passing mention” of the experts and their testimony. To the contrary, Attorney Marks argued that the jury should not credit the Government's experts for various reasons (e.g., bias, lack of explanation, lack of testing). The mere fact that these arguments failed to persuade the jury to acquit him does not make those arguments unreasonable strategic or tactical choices. See, e.g., Yarborough, 540 U.S. at 6, 124 S.Ct. 1 (“[D]eference to counsel's tactical decisions in his closing presentation is particularly importance because of the broad range of legitimate defense strategy at that stage.”). Accordingly, this argument will be rejected.

b. Requena's Filings

Requena also contends that Attorney McBride failed to adequately address the expert witnesses in his summation. This argument will be rejected for substantially the same reasons set forth supra: a review of the transcript shows that Attorney McBride provided a constitutionally adequate closing argument that offered the jury reasons to discredit the Government's expert witnesses while identifying several reasons to credit Dr. Erickson and/or Dr. DeCaprio. Trial Tr. at 2049–2056. As with Raymond's argument on this point, the mere fact that Attorney McBride failed to persuade the jury to acquit him does not somehow make his closing an unreasonable strategic or tactical choice. Yarborough, 540 U.S. at 6, 124 S.Ct. 1 (“[D]eference to counsel's tactical decisions in his closing presentation is particularly importance because of the broad range of legitimate defense strategy at that stage.”). Accordingly, this argument will also be rejected.

V. CONCLUSION

Defendants have not identified any conduct by their former attorneys that might amount to a viable claim of ineffective assistance of counsel.¹⁰ Instead, their arguments boil down to the kind of “Monday-morning quarterbacking” that our habeas cases discourage. United States v. Caracappa, 614 F.3d 30, 48 (2d Cir. 2010) (cleaned up).

The available record shows that Attorney Brooklier, Attorney Marks, and Attorney McBride acted “within the wide range of reasonable professional assistance” that this body of law is intended to police. Strickland, 466 U.S. at 689, 104 S.Ct. 2052. Contrary to defendants’ assertions, there was nothing even approaching a “breakdown in the adversarial process.” Id. at 687, 104 S.Ct. 2052.

With the benefit of hindsight, could one or both defendants have mounted a “better” or “more perfect” defense? Perhaps. But as Attorney Marks noted in advising Raymond to take the plea deal, “the consensus of opinion is that the juries disfavor these cases because they believe that the defendants are attempting to flout the drug laws with technical arguments.”

The record shows that, despite both defendants’ attorneys offering them a series of stern and repeated warnings that their chances at trial were “slim,” both men chose to put the Government to its burden of proof. That decision was theirs to make. But where, as here, defense counsel was constitutionally adequate, getting convicted by a jury on the basis of strong evidence is not a violation of the Sixth Amendment. It is due process at work.

Therefore, it is

ORDERED that

1. Petitioner-defendant Andrew Raymond's 28 U.S.C. § 2255 motion (Dkt. No. 357) is DENIED;

2. Petitioner-defendant Brian Requena's 28 U.S.C. § 2255 motion (Dkt. 356) is DENIED; and

3. No Certificate of Appealability ¹¹ shall be issued as to any of petitioners’ 28 U.S.C. § 2255 claims.

IT IS SO ORDERED.

FOOTNOTES

1.   This was Judge Mordue's criminal case. He handled the pre-trial motions, presided over the trial, and pronounced defendants’ sentences. The matter was initially given to Senior U.S. District Judge Thomas J. McAvoy following Judge Mordue's untimely passing, Dkt. No. 383, but has been reassigned to this Court for a decision on the pending § 2255 motions, Dkt. No. 392.

2.   These are novel chemical compounds with complex identifiers. For the readers’ sake, only the shorthand or abbreviated names will be used in this opinion.

3.   Attorney Brooklier led Raymond's defense until his unexpected death. At that time, his law partner, Attorney Marks, took over the case.

4.   Defendants sought other pre-trial relief, Dkt. Nos. 122, 123, that Judge Mordue denied in a separate opinion on July 5, 2017, Dkt. No. 179.

5.   In fact, by the time of trial, four of the chemical compounds named in the indictment had been added to Schedule I. Tr. at 1497–98.

6.   The eleven-volume trial transcript is cited by its consecutive pagination. Dkt. Nos. 311–328.

7.   Pagination of the briefing corresponds to CM/ECF.

8.   Elsewhere, Raymond contends that Attorney Brooklier's advice about the risks of a trial was not sufficiently detailed. Dkt. No. 357-2 at 14. But a review of the existing record confirms that Attorney Brooklier adequately discharged his legal obligations in connection with plea-bargaining when he: (1) told him about the Government's fourteen-year plea offer; (2) “advised [him] on the risks in proceeding to trial”; and (3) “suggested that [he] accept the plea deal.” Raymond Aff. ¶¶ 5, 7.

9.   Absent that kind of affirmative representation, a § 2255 petitioner is generally not entitled to habeas relief in this area of law. Lafler, 566 U.S. at 163, 132 S.Ct. 1376.

10.   Neither Raymond nor Requena have identified any conduct that might establish ineffective assistance. Accordingly, defendants’ request for an evidentiary hearing must be denied. Puglisi, 586 F.3d at 213. To the extent that any argument raised by either defendant has not been specifically discussed in this opinion, it has been considered and determined to be meritless.

11.   “A court may issue a certificate of appealability ‘only if the applicant has made a substantial showing of the denial of a constitutional right.’ ” Gray v. United States, 980 F.3d 264, 265 (2d Cir. 2020). “That standard is met when ‘reasonable jurists could debate whether (or for that matter, agree that) the petition should have been resolved in a different manner.’ ” Welch v. United States, 578 U.S. 120, 127, 136 S.Ct. 1257, 194 L.Ed.2d 387 (2016) (quoting Slack v. McDaniel, 529 U.S. 473, 484, 120 S.Ct. 1595, 146 L.Ed.2d 542 (2000)).

DAVID N. HURD, United States District Judge