Dwayne E. Sheppard v. Secretary, Florida Department of Corrections

• Court: Court of Appeals for the Eleventh Circuit
• Decided: January 22, 2026
• Docket: 24-10118
• Status: Unpublished

Opinion

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NOT FOR PUBLICATION

In the United States Court of Appeals For the Eleventh Circuit ____________________ No. 24-10118 Non-Argument Calendar ____________________

DWAYNE E. SHEPPARD, Petitioner-Appellant, versus

SECRETARY, FLORIDA DEPARTMENT OF CORRECTIONS, ATTORNEY GENERAL, STATE OF FLORIDA, Respondents-Appellees. ____________________ Appeal from the United States District Court for the Middle District of Florida D.C. Docket No. 8:12-cv-01127-SDM-AEP ____________________

Before WILLIAM PRYOR, Chief Judge, and LUCK and LAGOA, Circuit Judges. PER CURIAM: USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 2 of 10

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Dwayne Sheppard, a Florida prisoner serving a life sentence for sexual battery with a deadly weapon, appeals pro se the denial of his petition for a writ of habeas corpus. 28 U.S.C. § 2254. We granted Sheppard a certificate of appealability to address whether his sentence violates the Sixth Amendment. See Apprendi v. New Jer- sey, 530 U.S. 466 (2000); Blakely v. Washington, 542 U.S. 296 (2004). Because the state court reasonably concluded that the Apprendi er- ror was harmless, we affirm. I. BACKGROUND One night in June 1985 in Oldsmar, Florida, a naked intruder awoke J.J.F. as she slept with her then five-year-old daughter, held a sharp object to her as he forced her into the living room, raped her, and then forced her to shower off the evidence. It was not until 20 years later, in 2005, that J.J.F. identified Sheppard and another individual as suspects. Authorities charged Sheppard with sexual battery with a deadly weapon. See Fla. Stat. § 794.011(3). Sheppard proceeded to trial in 2008. At trial, J.J.F. testified that, on June 22, 1985, a naked intruder awoke her in the middle of the night. She was in bed with her five-year-old daughter. The man held a sharp object to her, told her to “be quiet,” “to come into the living room,” and not to “wake [her] daughter.” J.J.F. complied because she “didn’t want him to hurt her [daughter],” and “didn’t want her [daughter] to see any of this.” In the living room, the man told J.J.F. that he had just gotten out of jail and that some individuals were “willing to pay him [$500] to do this.” During this time, the man repeatedly sniffed USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 3 of 10

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from a canister. He touched J.J.F.’s breasts and vagina, placed his mouth on her vagina, engaged in vaginal sex, and ejaculated on her stomach. He then directed her to clean off in the shower. Authorities responded to J.J.F.’s home in the early morning hours of June 22, 1985. Detective Timothy Szmuigala testified that he and several other officers concluded that an intruder had re- moved a screen from the back window of J.J.F.’s home to gain en- try. Authorities recovered two fingerprints from the screen but could not identify a match. J.J.F.’s neighbor, Bernard Garele, testified that, on the even- ing of the crime, he heard a car door close and saw a man exit a blue “muscle car” with a white vinyl top. Other evidence estab- lished that, two weeks after the crime, Sheppard reported to au- thorities that someone had stolen his blue Mercury Cougar with a white vinyl top. And still other evidence established that, in Febru- ary 1986, police detained Sheppard while he was walking down a residential street near J.J.F.’s home at 1:00 a.m. Officers recovered a woman’s stockings, a knife, and a container for inhalants. Shep- pard told authorities that he intended to “scare some girls at a party.” Because Szmuigala could not develop any leads, he closed the case. It was not until 20 years later, in 2005, that Carol Beau- champ, a latent print examiner, began comparing fingerprints from cold cases to fingerprints in a computer database and discovered a match with Sheppard’s fingerprints. After determining that the fin- gerprints belonged to Sheppard, Detective Michael Bailey USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 4 of 10

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contacted J.J.F., who identified Sheppard and another individual as suspects. Bailey learned that Sheppard had ties to the Oldsmar area and contacted him in September 2005. Sheppard voluntarily agreed to come to the police station. During the interview, Sheppard told authorities that, in 1985, he lived in Clearwater, Florida, and worked as a painter. He admitted to being close friends with an individual who lived across the street from J.J.F., but he otherwise denied recognizing J.J.F.’s home and could not explain why his fingerprints were found on the screen. For his defense, Sheppard called a records custodian for the City of Oldsmar, who testified that, in June 1985, Sheppard was employed in the City’s water department. Sheppard also called Dwayne Milligan, who testified that, on June 21, 1985, he, Shep- pard, and other friends were out late celebrating the birth of Milli- gan’s daughter, and that they did not return to Milligan’s home un- til the early morning hours of June 22, 1985. Sheppard also testified that the City’s water department employed him in June 1985 and that, on June 21, 1985, he was with Milligan and slept at Milligan’s home. He testified that he may have touched the screen in J.J.F.’s backyard as part of his duties for the City, explaining that he often picked up items in residents’ yards when he checked their water meters. During the state’s rebuttal, J.J.F. testified that her water meter was in front of her home. The jury convicted Sheppard of sexual battery with a deadly weapon, and the court sentenced him to life imprisonment. The court departed upward from Sheppard’s sentencing-guideline USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 5 of 10

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range based, in part, on its findings of heightened premeditation and victim vulnerability. The Second District Court of Appeal af- firmed. Sheppard v. State, 31 So. 3d 183 (Fla. Dist. Ct. App. 2010). Sheppard challenged his life sentence under Apprendi and Blakley in various pro se postconviction motions and argued that the upward departure factors of heightened premeditation and victim vulnerability were never proved beyond a reasonable doubt to a jury. See Fla. R. Crim. P. 3.850; Fla. R. Crim. P. 3.800(a). The state postconviction court denied his Rule 3.850 motion and ruled that the claim had “no merit” because the trial court had articulated its reasons for departing from the guidelines, which was all that was required under Florida law. The Second District Court of Appeal affirmed. Sheppard v. State, 96 So. 3d 898 (Fla. Dist. Ct. App. 2012). The state postconviction court denied his Rule 3.800(a) motion as meritless and explained that any error was harmless because the trial record supported beyond a reasonable doubt that Sheppard acted with heightened premeditation and that J.J.F. was vulnerable. The Second District Court of Appeal affirmed. Sheppard v. State, 190 So. 3d 73 (Fla. Dist. Ct. App. 2016). In August 2019, Sheppard petitioned pro se for a writ of ha- beas corpus in the district court. See 28 U.S.C. § 2254. He alleged that, in imposing an upward departure at sentencing, the trial court violated his federal right to a jury under Apprendi by relying on facts not proved to a jury beyond a reasonable doubt. The district court denied his petition and ruled that the state postconviction court reasonably concluded that any Apprendi error was harmless. USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 6 of 10

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We granted a certificate of appealability on the following is- sue: “Whether Sheppard’s life sentence violates the rule announced in Apprendi v. New Jersey, 530 U.S. 466 (2000), Blakely v. Washington, 542 U.S. 296 (2004), and their progeny.” II. STANDARD OF REVIEW When a state court has adjudicated a constitutional error as harmless, a federal court may not grant habeas relief unless the pe- titioner clears two separate hurdles. See Brown v. Davenport, 596 U.S. 118, 134 (2022). First, he must establish that the error had a “sub- stantial and injurious effect or influence in determining the jury’s verdict” under Brecht v. Abrahamson, 507 U.S. 619 (1993). Id. at 133. Second, he must, under the Antiterrorism and Effective Death Pen- alty Act, establish that the state court’s harmlessness ruling was contrary to, or involved an unreasonable application of, clearly es- tablished federal law, or was based on an unreasonable determina- tion of the facts of his case. Id. at 127; see also 28 U.S.C. § 2254(d). This second test is a formidable barrier that permits relief only if the state court’s decision was “so lacking in justification that there was an error well understood and comprehended in existing law beyond any possibility for fairminded disagreement.” Harrington v. Richter, 562 U.S. 86, 103 (2011). Because a petitioner must satisfy both tests, “a federal court must deny relief to a state habeas peti- tioner who fails to satisfy [either test].” Brown, 596 U.S. at 134. III. DISCUSSION “Other than the fact of a prior conviction, any fact that in- creases the penalty for a crime beyond the prescribed statutory USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 7 of 10

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maximum must be submitted to a jury, and proved beyond a rea- sonable doubt.” Apprendi, 530 U.S. at 490. “[T]he ‘statutory maxi- mum’ for Apprendi purposes is the maximum sentence a judge may impose solely on the basis of the facts reflected in the jury verdict or ad- mitted by the defendant.” Blakely, 542 U.S. at 303. Under Apprendi and Blakley, Sheppard’s life sentence is un- constitutional because it is based on judicial findings—heightened premeditation and victim vulnerability—instead of findings made by a jury. Id. at 303-04. Although the statutory maximum for sexual battery in 1985 was life imprisonment, Fla. Stat. § 775.082(3) (1985), Sheppard was sentenced under Florida’s 1983 guidelines, which capped his permitted sentencing range at 12 years. Because any de- parture above that range required additional factual findings, the 12-year cap constituted the “statutory maximum” for Apprendi pur- poses. See Plott v. State, 148 So. 3d 90, 95 (Fla. 2014). By imposing a life sentence based on its own findings instead of those made by a jury, the trial court exceeded its authority and violated the Sixth Amendment. Yet Apprendi and Blakely violations are subject to harmless error review. Washington v. Recuenco, 548 U.S. 212 (2006). The state postconviction court, applying the standard in Chapman v. California, 386 U.S. 18, 24 (1967), ruled that any error under Apprendi and Blakely was harmless beyond a reasonable doubt. It ruled that any rational jury would have also found both heightened premeditation and that J.J.F. was vulnerable. Because this harmlessness determination is an adjudication on the merits of USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 8 of 10

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Sheppard’s claim, we review it under both section 2254(d) and Brecht. We conclude that the state court neither unreasonably ap- plied Chapman nor made an unreasonable determination of the facts under Florida law. We start with the state postconviction court’s determination that any rational jury would have also found that Sheppard’s actions established heightened premeditation. We then turn to its determination as to J.J.F.’s vulnerability. The state court reasonably determined that Sheppard’s con- duct established heightened premeditation. Under Florida law, pre- meditation supports a sentencing departure only if it consists of a “careful plan or prearranged design formulated with cold fore- thought.” State v. Obojes, 604 So. 2d 474, 475 (Fla. 1992). The Florida Supreme Court has distinguished between mere opportunity and deliberate planning. For example, stalking a victim for two weeks constitutes heightened premeditation, id., while taking a victim on a camping trip and committing a lewd act does not, see Marcott v. State, 650 So. 2d 977, 979 (Fla. 1995); see also Audano v. State, 641 So. 2d 1356, 1361 (Fla. Dist. Ct. App. 1994) (holding that heightened premeditation standard was not met where the defendant “built the trust of the victim over several months and then preyed on her unusual vulnerability”). Unlike the impulsive crimes of opportunity in Marcott and Audano, Sheppard’s brazen actions align with the “prearranged de- sign” in Obojes. See Obojes, 604 So. 2d at 475; cf. Marcott, 650 So. 2d at 1361; Audano, 641 So. 2d at 1361. Sheppard’s $500 bet USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 9 of 10

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transformed the assault from an impulse into a goal-oriented mis- sion with a financial incentive. His calculated approach—exploiting his knowledge of the neighborhood, parking down the street to avoid detection, and striking in the middle of the night—reveals a deliberate strategy to reduce his risk of criminal exposure. And this cold forethought extended to the assault. Sheppard armed himself in advance to ensure J.J.F.’s compliance and stripped naked to avoid leaving fiber evidence. His command to J.J.F. to shower off the evidence after the assault also establishes a degree of rehearsal and calculation that exceeds mere opportunity. The state court also reasonably determined that J.J.F. was particularly vulnerable. A victim’s vulnerability supports a depar- ture only when the offender is aware of a specific weakness that makes the victim “particularly” vulnerable. Hawkins v. State, 522 So. 2d 488, 490 (Fla. Dist. Ct. App. 1988). Florida courts have held that general helplessness or being asleep does not warrant a depar- ture. See Williams v. State, 492 So. 2d 1308, 1309 (Fla. 1986) (holding that the victim’s sleep at the time of a stabbing was insufficient); Grant v. State, 547 So. 2d 952, 953 (Fla. Dist. Ct. App. 1989) (same as to robbery). Likewise, defenselessness or gender is not a valid basis for departure because such factors are “common to nearly any” sexual battery or armed robbery. Wemett v. State, 567 So. 2d 882, 887 (Fla. 1990); Mathis v. State, 515 So. 2d 214, 216 (Fla. 1987). J.J.F. was targeted within a unique, situational trap that made her particularly vulnerable. See Hawkins, 522 So. 2d at 490; cf. Williams, 492 So. 2d at 1309; Grant, 547 So. 2d at 953. By USCA11 Case: 24-10118 Document: 33-1 Date Filed: 01/22/2026 Page: 10 of 10

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confronting her in the middle of the night as she lay beside her daughter, Sheppard leveraged J.J.F.’s maternal instincts against her. J.J.F.’s focus on the safety of her child paralyzed her ability to resist and created a vulnerability that exceeded mere gender or sleep. See Williams, 492 So. 2d at 1309; Wemett, 567 So. 2d at 887. Sheppard was aware of this dilemma and exploited it to ensure J.J.F.’s com- pliance. See Hawkins, 522 So. 2d at 490. Because the state court’s harmlessness ruling was not unreasonable under the Antiterrorism and Effective Death Penalty Act, Sheppard is ineligible for federal habeas relief regardless of whether he could satisfy Brecht. See Brown, 596 U.S. at 134. IV. CONCLUSION We AFFIRM the denial of Sheppard’s petition.