          Case: 16-17390   Date Filed: 12/20/2017   Page: 1 of 14


                                                        [DO NOT PUBLISH]



            IN THE UNITED STATES COURT OF APPEALS

                    FOR THE ELEVENTH CIRCUIT
                      ________________________

                            No. 16-17390
                        Non-Argument Calendar
                      ________________________

               D.C. Docket Nos. 5:14-cv-00034-MW-CJK,
                      5:12-cr-00025-MW-CJK-1


BRENNON KYLE HOLLEY,

                                                         Petitioner-Appellant,

                                  versus

UNITED STATES OF AMERICA,

                                                        Respondent-Appellee.

                      ________________________

               Appeal from the United States District Court
                   for the Northern District of Florida
                     ________________________

                           (December 20, 2017)

Before MARTIN, ROSENBAUM, and ANDERSON, Circuit Judges.

PER CURIAM:
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      Brennon Holley, a federal prisoner, appeals from the district court’s denial

of his motion to vacate or correct sentence, 28 U.S.C. § 2255, which he filed after

pleading guilty to one count of attempting to persuade, induce, or entice a minor to

engage in sexual activity. In his motion to vacate, Holley alleged, among other

things, ineffective assistance of plea counsel. After an evidentiary hearing, the

district court denied Holley’s motion, concluding that counsel’s performance was

not deficient and that any errors did not prejudice Holley. The district court then

granted a certificate of appealability on whether plea counsel rendered ineffective

assistance such that Holley should be permitted to withdraw his guilty plea.

Because we conclude that the court did not address one of Holley’s claims of

ineffective assistance, we vacate and remand for further proceedings.

                                 I. Background

A.    Underlying Criminal Proceedings

      In October 2012, Holley pled guilty under a written plea agreement to one

count of attempting to persuade, induce, or entice a minor to engage in sexual

activity, in violation of 18 U.S.C. § 2422(b). The agreed Statement of Facts

explained that on June 13, 2012, a Bay County Sheriff’s Office investigator, posing

as a 13-year-old girl named “Rhea,” responded to a sexually explicit advertisement

Holley posted on Craigslist. The investigator and Holley communicated by email,

text message, and phone calls over the next few days, and Holley, believing Rhea


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was only 13 years old, agreed to travel from Pensacola to Rhea’s house in Panama

City on Friday, June 15, 2012, to engage in sexual activity with her.

      Holley’s presentence investigation report calculated an advisory guideline

range of 78 to 97 months of imprisonment based on a total offense level of 27 and

a criminal history category of II. Because of the ten-year statutory minimum,

however, Holley’s guideline range became 120 months. See 18 U.S.C. § 2422(b).

      At sentencing in January 2013, Holley personally addressed the district court

and claimed that he had just recently learned of the mandatory minimum. He

explained,

      I did not know of minimum mandatory looking at the points that I
      scored out to before, before October 18th when I pled guilty to this
      offense. I just—I really wanted to put this behind me, and I pled and
      thought that I would do that time that was allotted. I wasn’t aware of
      the minimum mandatory. Now that I am aware of it, once again, I
      would like to get this behind me.

The court replied that it would consider allowing him to withdraw his guilty plea if

he did not know of or was confused about the mandatory minimum. In response,

Holley elaborated on his reasoning in pleading guilty:

      At the same time, Your Honor, I was told offenses of this nature are
      looked down upon understandably, quite understandably, and trials
      usually end up with 25 years to life. That’s basically the option I was
      given, or the option I weighed, was do I want to take this to trial and
      possibly do 25 years to life, or do I pled [sic] guilty and do 87 months
      in prison? Actually, I pled.




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      When the district court explained that it likely could not sentence Holley

below the mandatory minimum, Holley asked for additional time to consider his

options. The government did not oppose Holley’s request. Based on Holley’s

statements, however, the government reiterated that “[t]here [was] no 25 to life in

this case” and that the “only mandatory minimum” that applied was 10 years. The

court continued the sentencing hearing for three weeks.

      When sentencing resumed in February 2013, Holley indicated that he was

ready to go forward. The district court sentenced him to the minimum term of 120

months of imprisonment. Holley did not file a direct appeal.

B.    Post-Conviction Proceedings

      In 2014, Holley filed a pro se 28 U.S.C. § 2255 motion, which he later

amended, raising, among other claims, allegations of ineffective assistance of plea

counsel. In pertinent part, Holley claimed that counsel provided constitutionally

ineffective assistance by (a) failing to conduct a meaningful investigation;

(b) failing to explain various matters, including the elements of the charge against

him, the strength of the government’s case, and any available defenses, such as an

entrapment defense; and (c) advising him that exercising his right to a jury trial

would inevitably result in at least 25 years in prison.

      In a supplemental pro se filing, Holley submitted an affidavit swearing that

plea counsel told him that he would “inevitably receive” a prison term of 25 years


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to life if he went to trial. Out of fear of a more severe sentence, Holley stated, he

pled guilty. He also submitted affidavits from his grandmother and sister, who

swore that counsel made the same sentencing prediction to them.

      Finding that Holley’s claims warranted greater scrutiny and development, a

magistrate judge appointed habeas counsel, who then filed a supplemental brief in

support of Holley’s amended § 2255 motion. The magistrate judge set the matter

for an evidentiary hearing.

      Before the hearing, the parties submitted a joint pre-hearing stipulation and

summary listing the issues to be resolved. Holley stated that the issues were

whether counsel was ineffective in the following ways: (1) failing to properly

advise him of the elements of the offense and the strength of the government’s

case; (2) failing to explore and advise him of an entrapment defense or other

defenses; (3) failing to reasonably investigate the case; (4) advising him that he

would receive a sentence in excess of 20 years if he went to trial and lost; and

(5) failing to advise him about his appellate rights. The government, by contrast,

believed that the issues were narrower and related to the failure to file a direct

appeal, the sufficiency of the evidence to support the plea, and the viability of an

entrapment defense.

      An evidentiary hearing was held on May 11, 2016. Plea counsel was the

only witness to testify.      Counsel testified that he discussed with Holley the


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evidence, the elements of the offense, and any potential defenses, but that he

advised Holley to plead guilty because he believed that Holley was likely to lose at

trial. Counsel also testified that he talked with Holley about the range of possible

sentences. According to counsel, he advised Holley that a sentence of more than

10 years was unlikely if he pled guilty, but that there was a possibility of a more

severe sentence if he went to trial and lost. However, counsel was not asked

whether he told Holley that going to trial and losing would inevitably result in a

prison sentence of at least 25 years.

      Following the evidentiary hearing, and after receiving additional briefing

from the parties, the magistrate judge issued a report and recommendation

(“R&R”) that Holley’s amended § 2255 motion be granted. Addressing Holley’s

claims of ineffective assistance as a whole, the magistrate judge concluded that, for

a variety of reasons, “Holley was deprived of the critical opportunity to make a

meaningful and informed decision whether to go to trial.”

      After receiving the government’s objections and Holley’s response to them,

the district court issued an exhaustive 92-page order rejecting the R&R and

denying Holley’s amended § 2255 motion. The court conducted its own review of

the record, Holley’s amended § 2255 motion, and the counseled supplemental brief

in support of that motion, among other filings, and found that plea counsel’s




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performance was not deficient and that any errors by counsel did not prejudice

Holley.

      In particular, the district court determined that it was reasonable for counsel

to advise Holley to plead guilty because the evidence was sufficient to prove his

guilt beyond a reasonable doubt and a jury likely would have rejected an

entrapment defense. The court further found that counsel reasonably decided not

to investigate Holley’s alleged preference for older women because it was unlikely

to sway a jury. Finally, the court concluded that the reasonableness of counsel’s

advice to plead guilty was supported by the benefits in doing so. The court noted

that Holley “literally faced life imprisonment for his offense,” that the government

promised not to seek more than the mandatory minimum if Holley pled, and that he

would have faced a guideline range of 120 to 135 months of imprisonment after

trial. As to that last point, the court stated, “pleading guilty had a real benefit to

him by reducing the risk that the Court would sentence him at the high end of the

Guidelines range and add over a year to what he actually received.” However, the

court did not expressly address Holley’s claim that he was advised by counsel that

going to trial increased his likely sentence by at least 15 years, not just 15 months.

      Upon denying Holley’s amended § 2255 motion, the district court granted a

certificate of appealability on two issues: (1) whether plea counsel rendered

ineffective assistance such that Holley should be permitted to withdraw his guilty


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plea; (2) whether plea counsel failed to properly advise Holley of his appellate

rights such that he should be permitted the opportunity to file a direct appeal. On

appeal, Holley expressly waives review of the second issue, so our discussion is

limited to the first.

                                 II. Standard of Review

       Whether counsel rendered constitutionally ineffective assistance is a mixed

question of law and fact that we review de novo. Hagins v. United States, 267 F.3d

1202, 1204 (11th Cir. 2001).

                                    III. Discussion

       Holley’s main contention on appeal is that plea counsel unreasonably

advised him that he would likely receive a prison sentence of 25 years to life if he

went to trial and lost. Had he been properly advised that he was unlikely to receive

a sentence substantially above the 10-year mandatory minimum, Holley maintains,

he would have insisted on taking his chances at trial. See, e.g., Lee v. United

States, 137 S. Ct. 1958, 1966–67 (2017) (stating that, when the respective

consequences of a conviction after trial and by plea are, “from the defendant’s

perspective, similarly dire, even the smallest chance of success at trial may look

attractive”).

       The government responds that there is no evidence that Holley was so

advised by counsel. But, in fact, Holley’s comments at the initial sentencing


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hearing in January 2013 strongly suggest that he did receive that advice and that it

affected his decision to plead guilty. At that hearing, he stated,

       I was told offenses of this nature are looked down upon
       understandably, quite understandably, and trials usually end up with
       25 years to life. That’s basically the option I was given, or the
       option I weighed, was do I want to take this to trial and possibly do 25
       years to life, or do I ple[a]d guilty and do 87 months in prison?

(emphasis added).

       The district court did not expressly address Holley’s claim of ineffective

assistance based on counsel’s allegedly unreasonable sentencing advice, however,

so it never resolved whether counsel’s advice as to the respective consequences of

a conviction after trial or by plea was deficient or whether Holley was prejudiced

by counsel’s advice, whatever it was.

       District courts must resolve all claims for relief raised in a § 2255 motion,

regardless of whether habeas relief is granted or denied.1 See Clisby v. Jones, 960

F.2d 936, 935–36 (11th Cir. 1992) (en banc); Rhode v. United States, 583 F.3d

1289, 1291 (11th Cir. 2009) (extending Clisby to § 2255 motions). A claim for

relief is “any allegation of a constitutional violation.” Clisby, 960 F.2d at 936. A


       1
          We recognize that appellate review is generally limited to the issues in the certificate of
appealability, which, in this case, did not mention error under the rule of Clisby. See Murray v.
United States, 145 F.3d 1249, 1250 (11th Cir. 1998). Nevertheless, we cannot meaningfully
review whether plea counsel rendered ineffective assistance such that Holley should be permitted
to withdraw his guilty plea—the substantive issue specified in the certificate of appealability—
—when a claim necessary to determine that question remains unresolved. Cf. Callahan v.
Campbell, 396 F.3d 1287, 1288–89 (11th Cir. 2005) (finding error under Clisby after the district
court granted a certificate of appealability on substantive claims that it failed to address).
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defendant alleges a constitutional violation, and therefore a claim for relief, when

he alleges that counsel provided ineffective assistance in violation of his Sixth

Amendment rights. See Strickland v. Washington, 466 U.S. 668, 685–86 (1984).

      We cannot consider claims that the district court has not resolved in the first

instance. See Clisby, 960 F.2d at 935 (“[R]espondent urged us to consider the

ineffective assistance claims not addressed by the district court. This we clearly

cannot do.”). Instead, when a district court does not address all claims in a motion

to vacate, we “will vacate the district court’s judgment without prejudice and

remand the case for consideration of all remaining claims.” Id. at 938.

      Generally, an unresolved claim constitutes a Clisby error regardless of the

reason the claim was not resolved. Puiatti v. McNeil, 626 F.3d 1283, 1307 (11th

Cir. 2010). But a claim must be raised in a way that the district court cannot

misunderstand it in order for the district court to resolve it. Smith v. Sec’y, Dep’t of

Corr., 572 F.3d 1327, 1352 (11th Cir. 2009). In Smith, we held that a petitioner

failed to fairly present a legal argument to the district court when that argument

was mentioned in only one sentence of a 116-page habeas petition, without citing

any authority, and it was not mentioned in a 123-page supporting memorandum of

law. Id. In Dupree v. Warden, 715 F.3d 1295, 1299 (11th Cir. 2013), however, we

held that “two sentences found in the middle of a fifteen-page memorandum

attached to [a § 2254] petition” sufficiently raised an ineffective-assistance-of-


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counsel claim. Because the district court did not resolve the claim, we vacated and

remanded as a violation of the Clisby rule. Id.

      After reviewing the record here, we conclude that Holley adequately

presented the ineffective-assistance-of-counsel claim based on counsel’s allegedly

unreasonable prediction of the likely consequences after a trial. In a 22-page typed

attachment to his amended § 2255 form, Holley claimed, under “GROUND

SEVEN: Ineffective Assistance of Counsel,” which covered four pages, that he

was told by counsel that if he did not plead guilty, he would get a prison sentence

of 25 years to life. He then asserted that counsel’s advice on this point was itself

constitutionally deficient and induced him to plead guilty out of fear of a more

severe sentence. Thereafter, Holley submitted affidavits attesting that counsel

gave that advice to him, his sister, and his grandmother. Then, in the pre-hearing

stipulation and summary, he included among five ineffective-assistance claims to

be resolved “[w]hether counsel was ineffective, in violation of the Sixth

Amendment, . . . for . . . advising the Petitioner that he would receive a sentence of

20 years if he went to trial and lost.” Holley’s three sentences in the attachment to

his amended § 2255 motion, combined with his actions later in the proceedings,

were sufficient to raise the specific claim in a way that that district court could

understand it. See Dupree, 715 F.3d at 1299.




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       Moreover, Holley did not abandon that claim during the course of

proceedings below. To be sure, it was not a focus of his filings after habeas

counsel was appointed. And for that reason, we can certainly understand why the

claim slipped through the cracks. However, the record shows that his counseled

filings merely supplemented, rather than superseded, his pro se amended § 2255

motion. After being appointed, habeas counsel was given the option of filing an

amended § 2255 motion or a supplemental brief, and counsel chose the latter.

Then, before the evidentiary hearing, habeas counsel included among the issues to

be resolved at the evidentiary hearing the claim based on plea counsel’s allegedly

unreasonable sentencing advice. Finally, after the hearing, habeas counsel’s brief,

which focused on issues of evidentiary sufficiency and the viability of an

entrapment defense, made clear that it was “intended to supplement the arguments

Mr. Holley raised in his Amended Motion,” and that Holley did not intend to

abandon the issues discussed therein, apart from limited exceptions not relevant

here.2 Nor did the district court make any finding that Holley had abandoned the

ineffective-assistance claim based on plea counsel’s allegedly unreasonably

sentencing advice.




       2
          In the pre-hearing stipulation and summary, Holley expressly waived his claims that
the presentence investigation was flawed and that 18 U.S.C. § 2422(b) violates the Commerce
Clause of the United States Constitution.
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      Despite the district court’s commendably thorough and probing treatment of

Holley’s claims, we nevertheless conclude that it did not address his specific claim

that plea counsel provided ineffective assistance by advising him that he would

likely be sentenced to at least 25 years in prison if he went to trial. The court’s

factual findings do not permit resolution of that specific claim, and, without a

resolution as to that claim, we cannot meaningfully review whether plea counsel

rendered ineffective assistance such that Holley should be permitted to withdraw

his guilty plea. See Long v. United States, 626 F.3d 1167, 1170 (11th Cir. 2010)

(“[W]e have long required the district courts . . . to facilitate meaningful appellate

review by developing adequate factual records and making sufficiently clear

findings as to the key issues.”).

      Accordingly, we conclude that the district court violated Clisby when it did

not address Holley’s claim that plea counsel provided ineffective assistance by

unreasonably advising him that he would likely be sentenced to at least 25 years in

prison if he went to trial. We therefore vacate the district court’s judgment without

prejudice and remand for consideration of this claim. See Rhode, 583 F.3d 1292;

Clisby, 960 F.2d at 938. We decline to consider the other arguments Holley

presents on appeal and instead leave these matters to be addressed, as appropriate,

following the district court’s disposition of Holley’s remaining claim. See Clisby,

960 F.2d at 936 (“Policy considerations clearly favor the contemporaneous


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consideration of allegations of constitutional violations grounded in the same

factual basis . . . .”).

       VACATED AND REMANDED.




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