[DO NOT PUBLISH]

In the

United States Court of Appeals

For the Eleventh Circuit

____________________

No. 21-12955

Non-Argument Calendar

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RAYMOND HAILE, 

Petitioner-Appellant,

versus

UNITED STATES OF AMERICA, 

Respondent-Appellee.

____________________

Appeal from the United States District Court

for the Southern District of Florida

D.C. Docket No. 1:19-cv-22161-JLK

____________________

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Before WILSON, ROSENBAUM, and GRANT, Circuit Judges.

PER CURIAM:

Raymond Haile, a federal prisoner proceeding pro se, appeals the district court’s denial of his 28 U.S.C. § 2255 motion. We 

granted a certificate of appealability (COA) on whether Haile’s trial 

counsel was ineffective for misadvising him during plea negotiations that he had three qualifying convictions for the purposes of

the Armed Career Criminal Act (ACCA). After review, we find that 

Haile’s trial counsel properly considered the current case law at the 

time of Haile’s plea negotiations and thus was not ineffective for 

advising Haile that he had three qualifying convictions under 

ACCA. 

When faced with the denial of a § 2255 motion, we review 

legal conclusions de novo and factual findings for clear error. 

Brown v. United States, 942 F.3d 1069, 1072 (11th Cir. 2019) (per 

curiam). Section 2255 allows federal prisoners to obtain post-conviction relief and set aside prior convictions when a sentence “was 

imposed in violation of the Constitution or laws of the United 

States.” 28 U.S.C. § 2255(a). We review de novo a claim of ineffective assistance of counsel. Hagins v. United States, 267 F.3d 

1202, 1204 (11th Cir. 2001). 

To succeed on a claim of ineffective assistance of counsel, a 

movant must show that counsel’s performance was deficient and 

prejudiced him. Strickland v. Washington, 466 U.S. 668, 

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21-12955 Opinion of the Court 3

687 (1984). Counsel has a right to form strategies that are reasonable at the time of trial and to balance limited resources in accordance with effective tactics and strategies. Harrington v. Richter, 

562 U.S. 86, 107 (2011). An attorney does not render ineffective 

assistance by failing to make an argument that depends on a future 

development of law. Brewster v. Hetzel, 913 F.3d 1042, 1057 (11th 

Cir. 2019).

Under the ACCA, a defendant convicted of being a felon in 

possession of a firearm is subject to a mandatory minimum sentence of 15 years’ imprisonment if he has 3 prior convictions for a 

serious drug offense or violent felony “committed on occasions different from one another.” 18 U.S.C. § 924(e). 

In Wooden v. United States, the Supreme Court rejected the 

Sixth Circuit’s holding that the different-occasions provision was 

satisfied whenever crimes occurred sequentially instead of simultaneously. 142 S. Ct. 1063, 1068 (2022). Rather, the Supreme Court 

held that an inquiry into whether offenses occurred on separate occasions is multi-factored and requires considering the timing, location, character, and relationship of the offenses. Id. at 1070–71.

First, Haile’s argument that his counsel should have had anticipated the Supreme Court’s opinion in Wooden would affect 

whether his prior offense would serve as predicate offenses under 

ACCA lacks merit. As the Supreme Court stated in Strickland, 

courts must try to “eliminate the distorting effects of hindsight,” 

and must “evaluate the conduct from counsel’s perspective at the 

time.” 466 U.S. at 689. Haile pleaded guilty in November 2017 and 

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was sentenced in February 2018, over three years before the Supreme Court granted certiorari in Wooden. See 141 S. Ct. 1370 

(2021). Thus, Haile’s counsel cannot be ineffective for failing to 

anticipate any future development about how Supreme Court 

cases, like Wooden, would have on our different-occasions analysis. 

Second, before Wooden, we held that two crimes occurred 

on a different occasion because they were “successive rather than 

simultaneous.” United States v. Longoria, 874 F.3d 1278, 1281 

(11th Cir. 2017) (per curiam). We also stated that occasions separated by a week “constituted sufficient temporal distinctness under 

the ACCA.” Id. at 1283.1 Haile’s two serious drug offenses occurred over a year apart, and thus occurred on different occasions 

for the purposes of ACCA. Thus, under our precedent at the time 

of Haile’s guilty plea and sentencing, he had three qualifying convictions, and thus his counsel properly advised him that he was subject to the 15-year mandatory minimum under the ACCA. 

1 Although we have not specifically addressed how Wooden impacts our prior 

precedent, our decision in Longoria appears to follow Wooden’s reasoning 

that “a single factor—especially of time or place—can decisively differentiate 

occasions.” 142 S. Ct. at 1071. Thus, considering Wooden and the facts of 

Haile’s drug offenses, he would still have three qualifying offenses. 

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Thus, the district court did not err by finding that Haile’s 

counsel did not render ineffective assistance and denying his § 2255 

motion. 2 

AFFIRMED.

2 Because Haile’s claim lacks merit, we deny his motion to appoint counsel.

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