THEODORE SIMPSON v. SUPERINTENDENT LEONARD PORTUONDO (2026)

REPORT AND RECOMMENDATION TO HON. VERNON S. BRODERICK: MOTION TO REOPEN (DKT. 33)

In 1998, after a jury trial in New York State Supreme Court, Bronx County, the petitioner, Theodore Simpson (“Simpson”), was convicted for attempted murder and robbery. The Appellate Division denied his direct appeal, and the New York Court of Appeals denied leave to appeal. Simpson then filed a petition for habeas corpus in this Court, which the Court denied. (Dkt. 25.) See also Simpson v. Portuondo, No. 01-CV-8744, 2002 WL 31045862, at *12 (S.D.N.Y. June 4, 2002) (Report and Recommendation). Simpson, proceeding pro se, now moves pursuant to Federal Rule of Civil Procedure 60(b)(6) (“Rule 60(b)(6)”) seeking relief from the earlier denial of his petition. For the reasons set forth below, the motion should be DENIED as an improperly filed second habeas petition.

Background

On November 27, 1995, Simpson, Juan Carlos Francos, and Cesar Martinez were indicted for the attempted murder and robbery of Michael Smith. Simpson, 2002 WL 31045862 at *2. During trial, the court permitted a witness, Nelson Camacho, to testify to a conversation Camacho had had with Franco, during which Franco had implicitly incriminated Simpson. Id. at *3. Franco did not testify and was not subject to any cross-examination. Id. The trial court also allowed the prosecutor to display the disabled victim to the jury. Id. at *5. Following trial, on March 2, 1998, Simpson was convicted of Attempted Murder in the Second Degree, N.Y. Penal Law §§ 110 and 125.25(1); two counts of Robbery in the First Degree, N.Y. Penal Law § 160.15(1) and (3); and Robbery in the Second Degree, N.Y. Penal Law § 160.10(1). Id. at *2.

Simpson appealed his conviction to the Appellate Division, First Department, on the basis that: “(1) the convictions were contrary to the weight of the evidence; (2) his constitutional right to confrontation was violated when the trial court allowed a witness to testify to [Franco's] statements implicating Simpson; (3) it was error to allow the victim to be displayed to the jury; and (4) all the sentences should have been imposed to run concurrently.” Id. On June 6, 2000, the Appellate Division affirmed the entirety of Simpson's conviction, finding that (1) the verdict was based on legally sufficient evidence; (2) the trial court did not err in allowing the victim to be shown to the jury; (3) Simpson's right to confrontation claim was unpreserved and without merit, and; (4) the sentence was properly imposed. People v. Simpson, 273 A.D.2d 40, 40-41, 710 N.Y.S.2d 820 (1st Dep't 2000). On August 28, 2000, the New York Court of Appeals denied Simpson's application for leave to appeal. People v. Simpson, 95 N.Y.2d 871, 715 N.Y.S.2d 226 (2000).

Simpson then petitioned this Court for a writ of habeas corpus pursuant to 28 U.S.C. § 2254. Simpson, 2002 WL 31045862, at *3. Simpson raised the same claims in his petition as he did in his direct appeal. See id. at *3-11. On June 4, 2002, Judge Francis recommended that the petition be denied (Dkt. 14), and on March 31, 2003, the District Judge adopted Judge Francis's report and recommendation and denied Simpson's petition. (Dkt. 25.) First, the Court found that Simpson's right-to-confrontation argument was procedurally barred and could not be reviewed. Simpson, 2002 WL 31045862, at *3-5. Second, the Court found that Simpson's due process rights were not violated by the trial court permitting the prosecutor to display the victim to the jury, because the victim's injuries were relevant, and “the challenged procedure, even if erroneous, was not sufficiently material to constitute a due process violation.” Id. at *7. Third, the Court found that Simpson's challenge to the sufficiency of the evidence did not provide a basis to disturb the jury's verdict. Id. at *8-10. Fourth, the Court concluded that Simpson's challenge to his consecutive sentences was without merit because the “consecutive sentences for the attempted murder conviction and the robbery convictions were permissible under New York law.” Id. at *10-11. On June 2, 2003, Simpson filed his notice of appeal. (Dkt. 27.) On April 22, 2004, the Second Circuit dismissed Simpson's appeal as untimely. (Dkt. 30.)

Over sixteen years later, on July 29, 2020, Simpson filed a motion to vacate pursuant to Rule 60(b). (Dkt. 31.) On July 31, 2020, the Court summarily ordered the motion stricken because the case was closed in 2003, and the affidavit submitted in support of the motion referenced a different civil action number. (Dkt. 32.) More than five and a half years after the motion was stricken, Simpson filed the instant motion pursuant to Rule 60(b)(6), asking the Court to reopen the case. (Dkt. 33.) Simpson argues that recent Supreme Court decisions represent a change in the law requiring a different outcome than his prior habeas petition. (Id. at 3.)

Legal Standards

Rule 60(b) provides relief “from a final judgment, order, or proceeding.” Fed. R. Civ. P. 60(b). Subdivision (b)(6) is a “catchall category,” which “permits a court to reopen a judgment for any other reason that justifies relief.” Buck v. Davis, 580 U.S. 100, 123 (2017) (internal quotation marks omitted). Rule 60(b) may also be invoked to reopen a habeas proceeding. Gonzalez v. Crosby, 545 U.S. 524, 534 (2005) (“Rule 60(b) has an unquestionably valid role to play in habeas cases”). But “a Rule 60(b) motion has a different objective than a habeas petition.” Silva v. Keyser, No. 16-CV-7609, 2025 WL 3237889, at *2 (S.D.N.Y. Nov. 20, 2025) (quoting Carbone v. Cunningham, 857 F. Supp.2d 486, 488 (S.D.N.Y. 2012)), certificate of appealability denied, No. 25-3087, 2026 WL 1644033 (2d Cir. Apr. 24, 2026). “A motion challenges the integrity of the federal habeas proceedings – and is thus properly brought under Rule 60(b) – when, for example, it asserts that a court erroneously avoided deciding the merits of a claim for reasons such as failure to exhaust, procedural default, or statute-of-limitations bar.” Rodriguez v. United States, No. 00-CR-0761, 2018 WL 4091069, at *3 (S.D.N.Y. Aug. 28, 2018) (internal quotation marks omitted), R&R adopted, 2018 WL 4387552 (S.D.N.Y. Sept. 14, 2018). “Intervening developments in the law,” however, “by themselves rarely constitute the extraordinary circumstances required for relief under Rule 60(b)(6).” Agostini v. Felton, 521 U.S. 203, 239 (1997).

Where a Rule 60(b) motion attacks “the underlying [state court] conviction” rather than directly challenging the previous habeas proceeding, the motion “may be properly characterized as a successive habeas petition.” Harris v. United States, 367 F.3d 74, 82 (2d Cir. 2004) (emphasis omitted). For instance, a motion “contend[ing] that a subsequent change in substantive law is a ‘reason justifying relief’ ” under Rule 60(b)(6) “is in substance a successive habeas petition and should be treated accordingly.” Gonzalez, 545 U.S. at 531.

“Before a federal court can address a petitioner's second or successive federal habeas filing on the merits, the incarcerated filer must clear strict procedural hurdles that the Antiterrorism and Effective Death Penalty Act of 1996 (AEDPA) erects.” Rivers v. Guerrero, 605 U.S. 443, 446 (2025) (citing 28 U.S.C. § 2244(b)). “Specifically, before a district court may even entertain a successive habeas petition, the Second Circuit must certify that the petition (1) does not raise a ‘claim that has already been adjudicated in a previous petition’ and (2) that it ‘relies on either a new and retroactive rule of constitutional law or new facts showing a high probability of actual innocence.’ ” Robles v. Lempke, No. 09-CV-2636, 2018 WL 1320657, at *4 (E.D.N.Y. Mar. 14, 2018) (quoting Gonzalez, 545 U.S. at 529-30). Without authorization from the Court of Appeals, “district courts lack jurisdiction to consider the merits of a successive habeas petition.” Silva, 2025 WL 32327889, at *2 (citing Torres v. Senkowski, 316 F.3d 147, 151-52 (2d Cir. 2003)).

“If the court determines that a Rule 60(b) motion actually asserts claims of error in the underlying conviction or sentence and is therefore a successive [habeas] petition, the court has two procedural options.” Rodriguez v. United States, 164 F. Supp.3d 561, 566 (S.D.N.Y. 2016). First, “the court may treat the Rule 60(b) motion as a second or successive habeas petition, in which case it should be transferred to [the Court of Appeals] for possible certification ․” Harris, 367 F.3d at 82 (internal quotation marks omitted). Alternatively, “the court may simply deny the portion of the motion attacking the underlying conviction as beyond the scope of Rule 60(b).” Id. (internal quotation marks omitted). The Court of Appeals has cautioned district courts “not to recharacterize a portion of the 60(b) motion as a second or successive collateral attack and transfer it to [the Second Circuit] until the prisoner has been informed of the district court's intent to transfer and afforded a sufficient opportunity to avoid the transfer by withdrawing ․ the portion of his 60(b) motion that the district court believes presents new challenges to the underlying conviction.” Gitten v. United States, 311 F.3d 529, 534 (2d Cir. 2002). “[P]remature treatment of the converted portion of the 60(b) motion as a second collateral attack risks subjecting the prisoner not only to summary denial of that challenge but also to summary denial of any subsequent ․ challenge as an abuse of the writ.” Id. at 533.

Discussion

The entirety of Simpson's motion is properly characterized as a successive habeas petition, not a Rule 60(b) motion. The motion “does not identify any defect in the integrity of [Simpson's] prior federal habeas proceeding.” Silva, 2025 WL 3237889, at *3. Instead, the motion is predicated on the argument that recent Supreme Court decisions have changed the law governing the constitutionality of Simpson's state court conviction. (Dkt. 33 at 1-3.) For example, Simpson argues that the Supreme Court's decisions in Smith v. Arizona, 602 U.S. 779 (2024), and in Glossip v. Oklahoma, 604 U.S. 226 (2025), support Simpson's arguments that his right to confrontation was violated and that the victim should not have been displayed during the trial.¹ (Dkt. 33 at 1, 7-10.) Simpson also reiterates his insufficiency of the evidence claims. (Id. at 11-12.)

A Rule 60(b) motion like Simpson's – “based on a purported change in the substantive law governing the claim” – is properly characterized as a successive habeas petition; otherwise, Rule 60(b) “could be used to circumvent [§] 2244(b)(2)(A)’s dictate that the only new law on which a successive petition may rely is a new rule of constitutional law, made retroactive to cases on collateral review by the Supreme Court, that was previously unavailable.” Gonzalez, 545 U.S. at 531-32 (internal quotation marks omitted). Inasmuch as Simpson is “seek[ing] relief based on recent decisional law issued by the Supreme Court ․ rather than on the basis of errors that had affected the integrity of his prior habeas proceedings,” he can seek relief “in a successive habeas proceeding.” Rodriguez v. United States, No. 09-CV-2063, 2018 WL 4091069, at *5 (S.D.N.Y. Aug. 28, 2018).

As discussed above, the Court may either transfer the motion to the Court of Appeals for potential certification, or deny it as “beyond the scope of Rule 60(b).” Gitten, 311 F.3d at 533. To ensure that Simpson receives proper notice prior to transfer, and to give effect to the Second Circuit's stated preference, Harris, 367 F.3d at 82, the motion should be denied as beyond the scope of Rule 60(b). See Silva, 2025 WL 3237889, at *4 (dismissing, instead of transferring, a Rule 60(b) motion that was properly deemed a successive habeas motion); Rodriguez, 2018 WL 4091069, at *5 (same).

Conclusion

For the foregoing reasons, I recommend that Simpson's motion be DENIED. To the extent not discussed above, the Court has considered Simpson's arguments and found them to be either moot or without merit.

Deadline For Filing Objections And Preserving Appeal

Pursuant to 28 U.S.C. § 636(b)(1) and Rules 72, 6(a), and 6(d) of the Federal Rules of Civil Procedure, the parties shall have fourteen (14) days to file written objections to this Report and Recommendation. Any party shall have fourteen (14) days to file a written response to the other party's objections. Any such objections and responses shall be filed with the Clerk of the Court, with courtesy copies delivered to the Chambers of the Honorable Vernon S. Broderick, United States Courthouse, 40 Foley Square, New York, New York 10007, and to the Chambers of the undersigned, at United States Courthouse, 500 Pearl Street, New York, New York 10007. Any request for an extension of time for filing objections must be addressed to Judge Broderick. Failure to file timely objections will result in a waiver of the right to object and will preclude appellate review.

Copies transmitted this date to all parties of record. The Court respectfully requests the Clerk of Court to mail a copy of this Report and Recommendation to the pro se Petitioner:

Theodore Simpson

96A3862

Eastern Correctional Facility

30 Institution Road

P.O. Box 338

Napanoch, NY 12458-0338

FOOTNOTES

1.   Simpson also “bring[s] to this Court's attention the decisions,” among others, of BLOM Bank SAL v. Honickman, 605 U.S. 204 (2025) and Andrew v. White, 604 U.S. 86 (2025), arguing that they “readily justif[y] reopening [Simpson's] Federal Habeas proceeding under [Rule 60(b)].” (Dkt. 33 at 1-2.) To the contrary, in BLOM, a non-habeas case, the Supreme Court explained that “[o]ur more recent cases have consistently reaffirmed that Rule 60(b)(6) should only be applied in extraordinary circumstances,” and that the “Rule 60(b)(6) standard does not change when a party seeks to reopen his case to amend his complaint.” 605 U.S. at 212-213 (internal quotation marks and citations omitted). BLOM does not represent any significant change in applicable law, and it involved an inapt set of facts. In Andrew, the Supreme Court reaffirmed the principle that when a trial court permits introduction of evidence “that is so unduly prejudicial that it renders the trial fundamentally unfair, the Due Process Clause of the Fourteenth Amendment provides a mechanism for relief.” 604 U.S. at 88 (quoting Payne v. Tennessee, 501 U.S. 808, 825 (1991)). Andrew introduced no new applicable legal principles and concerns arguments directed to the merits of Simpson's state proceedings, not a purported defect in his prior habeas proceeding before this Court.

ROBERT W. LEHRBURGER UNITED STATES MAGISTRATE JUDGE