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Jeffery W. CAIN, Appellant-Petitioner v. STATE of Indiana, Appellee-Respondent
MEMORANDUM DECISION
Case Summary
[1] In 2010, Jeffery Cain was convicted of felony murder and Class B felony robbery while armed with a deadly weapon. Cain was sentenced to life without parole (“LWOP”), and his convictions and sentence were affirmed on direct appeal. See Cain v. State, 955 N.E.2d 714 (Ind. 2011). Cain petitioned for post-conviction relief (“PCR”), claiming that he had received ineffective assistance of appellate counsel. Following an evidentiary hearing, the post-conviction court denied Cain's claim for relief. We affirm.
Facts and Procedural History
[2] The underlying facts relating to the instant appeal are as follows:
In early May 2009, Cain was unemployed and living in Florida when he met Matthu Sanders. Sanders convinced Cain that there were job opportunities in Indiana, and the two of them traveled by motorcycle to Orland, Indiana. At some point, either during the trip or after arrival, Cain's motorcycle broke down and he was left without money or transportation, unable to return to Florida on his own.
In Indiana, Cain and Sanders stayed at the mobile home of Matthew Nelson, a long-time family friend of Sanders. Cain was also introduced by Sanders to a childhood friend, Clinton Daniel Hess. Hess had a long-standing dispute with one Raymond Morrow, to whom Hess owed $4000. Morrow owned and operated a flea market in DeKalb County.
On the afternoon of May 15, 2009, Morrow was found dead in his flea market. He had been shot three times: once in the back, once in the chest, and once in the head. The lock of his cash register had also been shot and the contents scattered about. Another bullet was found nearby, having passed through several clocks on a shelf. Morrow's wallet had been taken, along with several money bags from the cash drawer and some collectible coins. A Ruger Super Red Hawk and a Meriden revolver were missing from a display, as was a 9mm pistol that Morrow was known to carry in a holster on his hip.
Detective Mark Heffelfinger of the Indiana State Police began to investigate Morrow's murder, but after several days he had few leads. Then, on May 18, 2009, police in DeKalb County conducted an unrelated controlled buy of methamphetamine from Sanders. The buy took place at Nelson's trailer. After Sanders was arrested, a subsequent search of the trailer revealed two guns: a .44–.40 Vaquero revolver and a Ruger Super Red Hawk. One of the officers at the scene was aware that a Ruger Super Red Hawk was missing from the Morrow murder and contacted Detective Heffelfinger.
Detective Heffelfinger confirmed that the Super Red Hawk found at Nelson's mobile home was the missing weapon, and ballistics tests later identified the .44–.40 Vaquero as the gun that killed Morrow and shot the cash register and clocks. Subsequent interviews with Sanders, Nelson, Hess, and others implicated Cain as Morrow's murderer. Detective Heffelfinger obtained an arrest warrant for Cain—who was now back in Florida—and traveled to Florida, where local police assisted in arresting Cain on May 23, 2009.
Detective Heffelfinger interviewed Cain three times, starting that same day. During these interviews, Cain confessed to killing Morrow and robbing the flea market.
The State charged Cain with felony murder and robbery while armed with a deadly weapon. It later added a charge of intentional murder and sought [LWOP], listing two statutory aggravators: first, that Cain intentionally killed Morrow while committing robbery and, second, that Cain was hired to kill Morrow. It charged Sanders, Nelson, and Hess with the same crimes. All four were set to be tried separately and all four were represented by different appointed counsel.
At Cain's trial, Detective Heffelfinger, Nelson, and Cain testified. Hess was also permitted to testify, over Cain's objection. The jury found Cain guilty on all three counts and, following a separate sentencing phase, found the first charged aggravator beyond a reasonable doubt but not the second. It further found that the aggravating circumstances outweighed any mitigating circumstances and recommended [LWOP]. The trial court imposed this sentence to run concurrently with a twenty-year sentence for the armed robbery.
Cain, 955 N.E.2d at 716–17 (footnotes and internal record citations omitted, bracketed material added).
[3] On direct appeal, Cain argued that “Hess's testimony should have been excluded” and that the prosecutor had “made prejudicial statements during her closing argument at the sentencing phase of his trial.” Id. at 717. With regard to Hess's testimony, the Indiana Supreme Court noted that Hess had long been listed as a potential witness but, until the day of trial, had refused to testify. Id. at 718. The Supreme Court concluded that the prosecutor had not engaged in misconduct in her manner of negotiating a plea agreement with Hess on the first day of Cain's trial and that Cain had failed to show evidence of unfair surprise or prejudice resulting from Hess's decision to testify. Id. at 719–20. In concluding that the trial court had not abused its discretion by allowing Hess to testify, the Indiana Supreme Court stated that “Hess's testimony was neither the smoking gun in this case nor a devastating blow to Cain's defense. To the extent that either of those were present, they were provided by Cain's own confession: I'm the one that did it.” Id. at 720 (internal quotations omitted).
[4] As for the prosecutor's statements during closing argument at the sentencing hearing, the Indiana Supreme Court noted the challenged statement that an individual could potentially be released from incarceration early if a term of years was imposed but not if Cain was sentenced to LWOP. Id. at 721. The Indiana Supreme Court noted that Cain had neither objected to the statement nor requested an admonition, meaning that Cain was only entitled to relief if he could prove fundamental error. Id. The Supreme Court noted that “[t]he prosecutor was correct that there are multiple grounds for sentencing credit available to offenders serving fixed terms” and “[i]naccurate as the prosecutor's portrayal of these programs was, it was apparent from the record that the intentionality of Cain's conduct” was “very high.” Id. at 721, 722 (emphasis in original). The Indiana Supreme Court concluded that a “single paragraph in a closing argument that ran to over seven pages of transcript was not fundamental error.” Id. at 722.
[5] Cain petitioned for PCR on February 15, 2012, and amended his petition on June 14, 2023. Cain argued that his appellate counsel had provided ineffective assistance by failing to challenge the appropriateness of his sentence on direct appeal.
[6] Cain's appellate counsel, now-Judge Adam Squiller, acknowledged at the PCR evidentiary hearing that he had not argued on direct appeal that Cain's LWOP sentence was inappropriate. Judge Squiller testified that he had practiced law for nineteen years and that the majority of his practice had involved criminal appeals. He had been very familiar with Cain's case because of his own appellate preparation, he had been law partners with Cain's trial attorney, and the two of them had frequently discussed the case. Judge Squiller had been aware that a jury had found Cain guilty, had found that the aggravating factors had outweighed the mitigating factors, and had recommended a sentence of LWOP. Judge Squiller indicated that his appellate challenge on direct appeal had
mostly dealt with a surprise witness where a plea agreement was negotiated by the prosecutor during the trial after jury selection. Uh, and in -- in my opinion, that was a substantially stronger issue than any of the other issues that could have been raised, including the appropriateness of [LWOP]. The -- the issue of mitigation was in the record, but the record of mitigation was not substantial, in my opinion. And it appeared to me that raising secondary or tertiary issues would have diluted the strength of the primary issue, which is why I didn't raise that.
PCR Tr. Vol. II p. 17. Judge Squiller had believed that Hess's negotiated plea deal, which had resulted in Hess's last-minute agreement to testify at Cain's trial, had “[b]y far” been the strongest issue in Cain's favor on appeal. PCR Tr. Vol. II p. 17. The appropriateness of Cain's sentence was, in Judge Squiller's view, a “substantially weaker” argument. PCR Tr. Vol. II p. 17. Judge Squiller acknowledged that he had raised the second issue of prosecutorial misconduct and clarified that his decision to challenge the admission of Hess's testimony and the alleged prosecutorial misconduct at sentencing had been aimed at overturning Cain's conviction and obtaining a new trial.
[7] On July 2, 2024, the post-conviction court denied Cain's PCR petition. In doing so, the post-conviction court found the following:
24. As previously noted, appellate counsel felt his strongest argument was the “surprise witness argument.” In addition, sentence review would only open the possibility that Cain would receive a sentence of a number of years, rather than, had appellate counsel been successful on his “surprise witness” argument, a new trial with the possibility of exoneration.
25. [Appellate] counsel made a strategic decision, based upon his lengthy experience as a criminal trial and appellate attorney, to present the issues that he believed to be the strongest for [Cain]. He testified that an appeal based on a surprise witness during trial, which was disclosed after jury selection, constituted “a substantially stronger issue than any of the other issues that could have been raised,” including the appropriateness of an appeal of the [LWOP] sentence.
26. As previously stated, [Cain] has a significant criminal history that included 12 prior felony offenses, including two armed robbery convictions for which he was sentenced to concurrent sentences of 50 years each.
27. [Appellate] counsel's strategy for [Cain's] appeal, if successful, would have mandated a new trial for the murder charge. Mr. Cain was 52 years old at the time of his murder conviction in this case. Even if [Judge] Squiller challenged the sentence of [LWOP] and was successful under Appellate Rule 7(B), Mr. Cain was likely to spend much of the remainder of his life in prison. The Court does not find fault with this strategy and does not find that [Judge] Squiller's performance fell below an objective standard of reasonableness.
28. Further, even assuming [Judge] Squiller's performance was deficient, [Cain] has not shown that he was prejudiced. [Cain] must show that, but for [Judge] Squiller's alleged error, the result of the outcome would have been different. [Cain's] arguments place a large emphasis on Wilson v. State 157 N.E.3d 1163 (Ind. 2020) and similar cases. However, there are clearly stark contrasts between [Cain's] case and Wilson, the age of [Cain] and his criminal history being the most obvious of the many distinctions. Notably, the final paragraphs of the Indiana Supreme Court decision in Mr. Cain's case are instructive. The Court noted: “․ it seems apparent that the level intentionality in Cain's conduct (that being the charged aggravator) was very high[.]” Emphasis in original. “Accordingly, we affirm Cain's conviction and sentence.” Emphasis added. [Cain, 955 N.E.2d at 721].
Appellant's App. Vol. II pp. 74–75 (italics and underlining in original).
Discussion and Decision
[8] “Post-conviction procedures do not afford the petitioner with a super-appeal.” Williams v. State, 706 N.E.2d 149, 153 (Ind. 1999). “Instead, they create a narrow remedy for subsequent collateral challenges to convictions, challenges which must be based on grounds enumerated in the post-conviction rules.” Id. A petitioner who has been denied post-conviction relief appeals from a negative judgment and as a result, faces a rigorous standard of review on appeal. Dewitt v. State, 755 N.E.2d 167, 169 (Ind. 2001); Collier v. State, 715 N.E.2d 940, 942 (Ind. Ct. App. 1999), trans. denied.
[9] Post-conviction proceedings are civil in nature. Stevens v. State, 770 N.E.2d 739, 745 (Ind. 2002). Therefore, in order to prevail, a petitioner must establish his claims by a preponderance of the evidence. Ind. Post-Conviction Rule 1(5); Stevens, 770 N.E.2d at 745. When appealing from the denial of a PCR petition, a petitioner must convince this court that the evidence, taken as a whole, “leads unerringly and unmistakably to a decision opposite that reached by the post-conviction court.” Stevens, 770 N.E.2d at 745. “In other words, the defendant must convince this Court that there is no way within the law that the court below could have reached the decision it did.” Id. (emphasis in original). “It is only where the evidence is without conflict and leads to but one conclusion, and the post-conviction court has reached the opposite conclusion, that its decision will be disturbed as contrary to law.” Godby v. State, 809 N.E.2d 480, 482 (Ind. Ct. App. 2004), trans. denied. “The post-conviction court is the sole judge of the weight of the evidence and the credibility of witnesses.” Fisher v. State, 810 N.E.2d 674, 679 (Ind. 2004).
[10] Cain contends that the post-conviction court erred in rejecting his claim that his appellate counsel had rendered ineffective assistance. “The right to effective counsel is rooted in the Sixth Amendment of the United States Constitution.” Taylor v. State, 840 N.E.2d 324, 331 (Ind. 2006). “ ‘The Sixth Amendment recognizes the right to the assistance of counsel because it envisions counsel's playing a role that is critical to the ability of the adversarial system to produce just results.’ ” Id. (quoting Strickland v. Washington, 466 U.S. 668, 685 (1984)). “ ‘The benchmark for judging any claim of ineffectiveness must be whether counsel's conduct so undermined the proper functioning of the adversarial process that the trial cannot be relied on as having produced a just result.’ ” Id. (quoting Strickland, 466 U.S. at 686).
[11] A successful claim for ineffective assistance of counsel must satisfy two components. Reed v. State, 866 N.E.2d 767, 769 (Ind. 2007). Under the first prong, the petitioner must establish that counsel's performance was deficient by demonstrating that counsel's representation “fell below an objective standard of reasonableness, committing errors so serious that the defendant did not have the ‘counsel’ guaranteed by the Sixth Amendment.” Id. (internal quotation omitted). “We recognize that even the finest, most experienced criminal defense attorneys may not agree on the ideal strategy or the most effective way to represent a client,” and therefore, under this prong, we will assume that counsel performed adequately and defer to counsel's strategic and tactical decisions. Smith v. State, 765 N.E.2d 578, 585 (Ind. 2002). “Isolated mistakes, poor strategy, inexperience, and instances of bad judgment do not necessarily render representation ineffective.” Id.
[12] Under the second prong, the petitioner must show that the deficient performance resulted in prejudice. Reed, 866 N.E.2d at 769. A petitioner may show prejudice by demonstrating that there is “a reasonable probability (i.e. a probability sufficient to undermine confidence in the outcome) that, but for counsel's errors, the result of the proceeding would have been different.” Id. (italics added, internal quotation omitted).
[13] A petitioner's failure to satisfy either prong will cause the ineffective assistance of counsel claim to fail. See Williams, 706 N.E.2d at 154. Stated differently, “[a]lthough the two parts of the Strickland test are separate inquires, a claim may be disposed of on either prong.” Grinstead v. State, 845 N.E.2d 1027, 1031 (Ind. 2006) (citing Williams, 706 N.E.2d at 154). The post-conviction court determined that Cain failed to demonstrate either deficient performance or prejudice. We agree.
[14] The PCR record establishes that appellate counsel had made the strategic decision to challenge Cain's conviction and sentence in a manner that, if successful, would have resulted in a new trial or a new sentencing hearing. As the post-conviction court noted, Cain was fifty-two years old at the time he was convicted of murder and Class B felony robbery, meaning that it was likely that Cain would spend most, if not the rest, of his life in prison even if his sentence was reduced from LWOP to a term of years typical for a murder conviction. Cain's appellate counsel testified that he had believed that Hess's negotiated plea deal, which had resulted in Hess's last-minute agreement to testify at Cain's trial, had “[b]y far” been the strongest issue in Cain's favor on appeal. PCR Tr. Vol. II p. 17. Moreover, counsel had believed that the appropriateness of Cain's sentence was, given the facts and circumstances of the case, a “substantially weaker” argument. PCR Tr. Vol. II p. 17. Though appellate counsel's approach was ultimately unsuccessful, we will not second-guess counsel's reasonable professional judgment and tactical decisions regarding the strengths and weaknesses of the potential claims available on direct appeal. See Strickland, 466 U.S. at 690 (“[S]trategic choices made after thorough investigation of law and facts relevant to plausible options are virtually unchallengeable[.]”); Danks v. State, 733 N.E.2d 474, 486 (Ind. Ct. App. 2000) (“[W]e do not second-guess strategic decisions requiring reasonable professional judgment even if the strategy or tactic, in hindsight, did not best serve the defendant's interests.”), trans. denied. As the post-conviction court found, Cain has failed to establish that his appellate counsel provided deficient performance on direct appeal.
[15] Furthermore, while a post-conviction claim is appropriately denied if the petitioner fails to establish either deficient performance or prejudice, we briefly note that Cain has also failed to establish prejudice. Again, in order to show prejudice, a petitioner must demonstrate that there is a reasonable probability that the outcome of the proceeding would have been different “but for” the alleged error. Reed, 866 N.E.2d at 769. In this case, both the jury and the trial court had been aware of the proffered mitigating circumstances but had found that such circumstances had been outweighed by the aggravating factors. Cain had helped plan the robbery of Morrow before robbing and murdering him. Morrow had been shot three times, and three firearms and money had been stolen from Morrow's flea market. In addition, Cain had a significant criminal history, including prior convictions for robbery and other violent offenses, and had fled the jurisdiction after the robbery and murder in an apparent attempt to avoid arrest. Based on these facts, we believe that it is unlikely that the Indiana Supreme Court, on direct appeal, would have overturned these determinations upon review. Cain has failed to establish a reasonable probability that “but for” his counsel's alleged error, the result of his trial would have been different. See id.
[16] The judgment of the post-conviction court is affirmed.
Bradford, Judge.
Pyle, J., and Kenworthy, J., concur.
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Docket No: Court of Appeals Case No. 24A-PC-1802
Decided: December 02, 2025
Court: Court of Appeals of Indiana.
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