Roscoe v. United States of America

Filing 11

MEMORANDUM OPINION. Signed by Judge James H Hancock on 10/16/2013. (JLC)

FILED
2013 Oct-16 AM 09:45
U.S. DISTRICT COURT
N.D. OF ALABAMA

IN THE UNITED STATES DISTRICT COURT
FOR THE NORTHERN DISTRICT OF ALABAMA
SOUTHERN DIVISION

RONALD ROSCOE,

)

Movant/Defendant,

)

v.

)

UNITED STATES OF AMERICA,

)

Respondent.

2:11-cr-37-JHH-RRA
2:13-cv-8006-JHH

)

MEMORANDUM OPINION
The court has before it Movant Ronald Roscoe’s Motion (Doc. #1) to Vacate,
Set Aside, or Correct Sentence Pursuant to 28 U.S.C. § 2255, filed on March 21,
2013. Pursuant to the court’s orders of March 28, 2013 (Doc. # 2) and April 15, 2013
(Doc. # 4), the United States Government filed a Response (Doc. #5) in opposition
to Roscoe’s Section 2255 Motion on May 15, 2013. In its response, the Government
seeks to have the Motion to Vacate (Doc. #1) dismissed in its entirety, without an
evidentiary hearing.1 (See Doc. #5 at 2, 33.)
Movant responded to the Government’s opposition on June 7, 2013. (Doc. #6.)
1

The Government attached the following exhibits to its response: Affidavit of Randy
Dempsey; Transcript of the Plea Hearing; Transcript of the Sentencing Hearing; Roscoe’s
opening brief on appeal; United States of America’s Motion to Dismiss the Appeal; Roscoe’s
Reply brief on appeal; final order on appeal of the Eleventh Circuit.

Additionally, on July 8, 2013 Movant filed a Motion (Doc. #7) to Take Judicial
Notice of the Supreme Court’s Decision in Descamps v. United States. The
Government filed a Response (Doc. #8) to the Motion and Movant filed a Reply
(Doc. #9). The court granted the Motion (Doc. #7) to Take Judicial Notice, stating
that it would address the additional argument made by Roscoe when the court
addressed Roscoe’s § 2255 petition. (See Doc. #10.)
After careful consideration of all the argument presented by Roscoe and the
Government, as well as the applicable law in this Circuit, the court concludes that
Roscoe’s Motion (Doc. #1) to Vacate, Set Aside, or Correct Sentence Pursuant to 28
U.S.C. § 2255 is due to be dismissed in its entirety for the following reasons.
I. Background
On February 2, 2011, A federal grand jury returned a one-count indictment
against Ronald Roscoe, changing him with being a felon in possession of a firearm
in violation of 18 U.S.C. § 922(g)(1). On February 16, 2011 Roscoe appeared with
defense counsel Scott Brower before United States Magistrate Judge Robert R.
Armstrong, Jr., pleaded not guilty, and was remanded to the custody of the United
States Marshall. Later that month, Roscoe retained defense attorney Randy Dempsey
to represent him.

2

A. Plea of Guilty
After Roscoe retained Dempsey as his attorney, Dempsey investigated
Roscoe’s criminal history and determined that he had one “adjudication” and two
criminal convictions that potentially qualified as “crimes of violence” or “serious
drug offenses” that could trigger the ACCA enhancement found in 18 U.S.C. §
924(e)(1). (See Aff. of Randy Dempsey ¶ 3.) Those three offenses were as follows:
(1) a November 5, 1999 youthful-offender adjudication by the Jefferson
County, Alabama Circuit Court arising out of a first-degree robbery charge;
(2) a June 13, 2005 first-degree unlawful-possession-of marijuana conviction
in the Jefferson County Circuit Court; and
(3) a June 13, 2005 murder conviction in the Jefferson County Circuit Court.
(Id.) Dempsey reviewed the government’s evidence against Roscoe. (Id. ¶ 4.) He
determined that the government expected to present evidence at trial showing that,
while Roscoe was being questioned by officers of the Birmingham, Alabama Police
Department in December 2010, Roscoe shoved one of them and tried to flee. (Id.)
Subsequently, while wrestling with Roscoe, the officers found a semiautomatic pistol
that the defendant had concealed in his clothing. (See id.)
Dempsey met with Roscoe on several occasions and reviewed the case
evidence and Roscoe’s criminal history, including the adjudication and convictions
described above. (Id. ¶ 5.) Dempsey and Roscoe discussed the advantages and
3

disadvantages of a plea agreement. (Id.) Dempsey advised Roscoe that portions of
his criminal history (i.e., the youthful-offender adjudication arising from the
first-degree robbery charge, the marijuana conviction, and the murder conviction)
could, if he was found guilty of the felon-in-possession charge through plea or at trial,
qualify him for the ACCA enhancement. (Id. ¶ 6.) This, in turn, would result in
prison sentence that could be as long as life in prison, and no less than 15 years. (Id.)
Sometime later, Dempsey received a proposed plea agreement from the
government. (Id. ¶ 7.) Dempsey discussed the entire proposed agreement with
Roscoe and reviewed all of its terms with him. (Id.) Section I of the proposed
agreement informed Roscoe that he could be imprisoned for no less than 15 years if
he was determined to be an Armed Career Criminal:
I. MAXIMUM PUNISHMENT
The defendant understands that the maximum
statutory punishment that may be imposed for the crime of
being a felon in possession of a firearm, in violation of
Title 18, United States Code, Section 922(g)(1), as charged
in COUNT ONE, is:
a.

Imprisonment for not more than 10
years (**Subject to provisions of the
Armed Career Criminal Act, 18 U.S.C.
§ 924(e) - In the event that the
defendant is determined to be an
Armed Career Criminal, per 18 U.S.C.
§ 924(e), he shall be imprisoned for not
4

less that 15 years, and could be
imprisoned for life)
(Plea Agreement at 1-2.) Section IV contained language expressly limiting Roscoe’s
right to appeal his conviction and sentence unless it was in excess of the applicable
statutory or guidelines maximum terms. (Id. at 6-7.) The plea agreement specifically
states as follows as it relates to this waiver:
IV.

WAIVER OF RIGHT TO APPEAL AND POSTCONVICTION RELIEF

In consideration of the recommended disposition
of this case, I, RONALD ROSCOE, hereby waive and
give up my right to appeal my conviction and/or
sentence in this case, as well as any fines, restitution,
and forfeiture orders, the Court might impose.
Further, I waive and give up the right to challenge my
conviction and/or sentence, any fines, restitution,
forfeiture orders imposed or the manner in which my
conviction and/or sentence, any fine, restitution, and
forfeiture orders were determined in any postconviction proceeding, including, but not limited to, a
motion brought under 28 U.S.C. § 2255.
The defendant reserves the right to contest in an
appeal or post-conviction proceeding either or both of
the following:
(a)

(b)

Any sentence imposed in excess of
the applicable statutory maximum
sentence(s); and
Any sentence imposted in excess of
the guideline sentencing range
determined by the Court at the time
5

sentence is imposed.
The defendant acknowledges that before giving
up these rights, the defendant discussed the Federal
Sentencing Guidelines and their application to the
defendant’s case with the defendant’s attorney, who
explained them to the defendant’s satisfaction. The
defendant further acknowledges and understands that
the government retains its right to appeal where
authorized by statute.
I, RONALD ROSCOE, hereby place my
signature on the line directly below to signify that I
fully understand the foregoing paragraphs, and that I
am knowingly and voluntarily entering into this waiver.
(Id.) (emphasis in original.) Dempsey informed Roscoe that there was a chance that
the appeal waiver could bar any appeal of the ACCA enhancement. (Dempsey Aff.
¶ 7.)
Dempsey told Roscoe that, after reviewing the government’s evidence, he
believed that entering into the plea agreement would be in Roscoe’s best interest. (Id.
¶ 8.) That being said, Dempsey also counseled Roscoe that only Roscoe could make
the decision whether to take the plea offer, enter a blind plea, or proceed to trial. (Id.)
Roscoe accepted the plea offer. (Id. ¶ 9.) Roscoe signed and initialed the plea
agreement in Dempsey’s presence, and Dempsey returned it to the government.2 (Id.)
2

Roscoe initialed the two pages of the agreement that contained the language regarding
maximum punishment. (Plea Agreement at 1-2.) He also initialed the two pages that contained
the language regarding the waiver of his right to appeal and post-conviction relief. (Id. at 6-7.)

6

The government’s attorney signed the agreement and then filed it into Court on
March 25, 2011.
The plea hearing was help on March 29, 2011 before the court. At the
beginning of the hearing, the court placed Roscoe under oath. (Plea Transcr. at 2-3.)
The court then told Roscoe to interrupt the proceedings to ask questions if anything
occurred during the hearing that he did not fully understand:
The Court: Mr. Roscoe, if anything is said here today that you do not
fully understand or if anything takes place in this
courtroom this morning that you do not fully understand,
I want you to interrupt the proceedings. Just ask me to stop
the proceedings and ask me to clear the matter up for you
or ask me to give you the opportunity to talk privately with
Mr. Dempsey, your attorney, so that he can answer
your questions and clear the matter up. Do you understand
that?
Roscoe:

Yes, sir.

(Id. at 3.)
The court first addressed Dempsey regarding the plea agreement and Roscoe’s
understanding of that agreement. Dempsey confirmed that the following: (1) that the
agreement set forth “everything that [Dempsey was] aware of that [Roscoe was]
relying upon at [that] time by way of a plea bargain or plea agreement”; (2) that
Dempsey had ample time to fully discuss the plea agreement with Roscoe prior to
Roscoe also placed his signature directly below the language regarding the waiver. (Id. at 7.)

7

Roscoe signing the agreement; (3) that Roscoe did not have any questions for
Dempsey that he was unable to answer about the agreement’s meaning or the way in
which it would function; and (4) that Dempsey had fully discussed the agreement’s
appeal-waiver provision with Roscoe. (Id. at 5-6.) Roscoe did not interrupt the court
or dispute Dempsey’s representations while he was speaking to the court about the
plea agreement. (See id.)
The court next addressed Roscoe, who confirmed that Dempsey had thoroughly
discussed the terms of the plea agreement with him:
The Court: . . . . I have here and you have there a written
plea agreement that bears your signature on page 13. It also
bears your signature on page 4 stipulating to certain facts
that are set forth thereon that page, and also signed by you
on page 7 waiving with certain limited exceptions your
right to appeal the conviction and sentence that may be
imposed in this case.
Does that document which has been filed with the Court set
forth everything that you are relying upon at this time by
way of a plea bargain or plea agreement with the
Government?
Roscoe:

Yes, sir.

The Court: Before you signed the agreement, did you have
sufficient opportunity to fully discuss it with Mr.
Dempsey?
Roscoe:

Yes, sir.

8

The Court: Did you have any questions of him with regard
to the meaning of the agreement or how it might function
that Mr. Dempsey was not able to answer to your
satisfaction?
Roscoe:

No, sir.

....
The Court: Has anyone promised you anything or
threatened you in any way to encourage you to enter this
plea of guilty?
Roscoe:

No, sir.

(Id. at 6-7.) The court continued speaking to Roscoe and described the maximum
criminal penalties that he could face by pleading guilty, and Roscoe stated that he
understood those penalties:
The Court: Mr. Roscoe, I am obligated at the time that I
take a plea of guilty from any defendant to set forth or
outline for the defendant the absolute maximum penalty
that could be imposed for the offense, and I’m about to do
that. I’m about to do that not to intimidate you or to
suggest that I’m thinking in terms of anything like that. I
have no idea what sentence is going to be appropriate. But
I do have the obligation to at least inform you of that fact.
Do you understand?
Roscoe:

Yes, sir.

The Court: The maximum sentence that could be imposed
as reflected in the plea agreement would be a fine of not
more than $250,000 and a custodial sentence of not more
than 10 years, any custodial sentence to be followed by a
9

term of not more that [sic] three years supervised release.
Now, that’s the normal maximum penalty. However, if you
have what they refer to as two qualifying convictions
committed at the same time of aggravated offenses or
heavy drug matters or what have you – I’m sure you have
talked that over with him – but if you have had two or more
of those, then the maximum penalty changes materially as
set out there in the plea agreement.
In other words, the custodial sentence would be not less
than 15 years and not more than life, with a not-more-than
5-year term of supervised release, with the fine staying the
same. Do you understand that?
Roscoe:

Yes, sir.

The Court: And that’s fully set forth in the plea
agreement. Did you understand that when you discussed
it with Mr. Dempsey?
Roscoe:

Yes, sir.

The Court: Is there anything that prevents you from
understanding anything that I’m saying to you at this time
or that prevents you from understanding anything that Mr.
Dempsey says to you when he discusses this matter with
you or that prevents you from understanding the nature of
the proceedings here today or the charges preferred [sic]
against you? Is there anything that prevents you from
understanding any of that?3
Roscoe: No, sir.
(Id. at 7-9.)
3

The court asked Roscoe whether he had taken any drugs or medication within the past
72 hours - he had only taken medication for his eye. (Plea Transcr. at 9.)

10

At this point, the court explained the indictment to Roscoe and ensured that
Dempsey had been given ample time to fully investigate the charges and generally
counsel Roscoe. (Id. at 9-10.) The court also explained the elements of the section
922(g)(1) charge. (Id. at 10-11.) The court then had the government outline the facts
that it expected to prove if there was a trial of the case. (Id. at 11-13.) When the
government finished outlining the facts, Roscoe agreed that they were substantially
correct. (Id. at 13.) Roscoe acknowledged that he was not required to plead guilty
to the 922(g)(1) charge, and understood that he was free to withdraw his plea and
maintain his innocence. (Id.) However, he stated that he still wanted to plead guilty,
and the court accepted his guilty plea and set the matter for sentencing. (Id. at 13-14.)
B. Sentencing
Before the sentencing hearing, the Probation Office issued a Presentence
Investigation Report (“PSR”) on May 17, 2011. The PSR listed Roscoe’s three prior
adjudications/convictions that qualified him as an Armed Career Criminal under 18
U.S.C. § 924(e). The PSR concluded that Roscoe was due to receive a sentence of
between 15 years and life in prison.
Roscoe remained represented by Dempsey during the sentencing phase, and
Roscoe objected to the PSR for a variety of reasons. Specifically, Roscoe argued that
the youthful-offender adjudication and the marijuana conviction were not felonies
11

that qualified him for the ACCA enhancement. The government opposed these
objections.
A sentencing hearing was held before the court on June 30, 2011. At
sentencing, the court overruled Roscoe’s objections to the PSR, applied the ACCA
enhancement, and sentenced Roscoe to 180 months imprisonment.4 (Sentencing
Trans.) After the hearing, the court entered a final judgment memorializing the 180month sentence.
C. Direct Appeal
Dempsey represented Roscoe on the direct appeal of his sentence to the
Eleventh Circuit. Roscoe specifically argued that the court should not have applied
of the ACCA enhancement. (See Govt Exh. 4.) The government responded with a
motion to dismiss, arguing that Roscoe’s appeal was barred by the appeal-waiver
provision in his plea agreement. (See Govt Exh. 5.)
Roscoe replied by arguing that he had not knowingly and voluntarily waived
his right to appeal the application of the ACCA enhancement because the trial court
had not discussed with him the “full implications” of the waiver provision. (See Govt

4

Although the court stated during the sentencing hearing that it believed that Roscoe
could raise the application of the ACCA enhancement on appeal notwithstanding the waiver
provision, (Sentencing Transcr. at 7-8, 14-15), the Eleventh Circuit clearly disagreed and
overruled the court’s interpretation of the appeal waiver when it dismissed Roscoe’s appeal of
the ACCA enhancement based on the appeal waiver alone. (See Govt Exh. 7.)

12

Exh. 6 at 8.) Roscoe also argued that, because both Dempsey and the trial court
believed that he had not waived his right to appeal his sentence, it was clear that
Roscoe had believed the same, and therefore had not knowingly and voluntarily
waived his appellate rights. (Id. at 9-11.)
The Eleventh Circuit granted the government’s motion to dismiss pursuant to
the appeal waiver. United States v. Roscoe, No. 11-13233-BB (11th Cir. Jan. 18,
2012). (Govt Exh. 7.)

Roscoe moved to reconsider this order, but the Eleventh

Circuit denied his motion.
D. Section 2255 Petition
On March 21, 2013, Roscoe timely filed a petition for relief under 28 U.S.C.
§ 2255. (Doc. #1.) Roscoe’s petition raises four arguments. The first three are
claims of ineffective assistance of counsel: (1) that the appeal waiver in the plea
agreement was entered into “unknowingly, involuntarily, and unintelligently due to
counsel’s ineffective assistance during the plea stage”; (2) that Dempsey’s
ineffectiveness in allowing Roscoe to unknowingly agree to the appeal waiver created
a conflict of interest, and that Dempsey was ineffective for failing to withdraw as
counsel after sentencing so that new, conflict-free counsel could have been appointed;
and (3) that Dempsey was ineffective on appeal for “failing to raise the ‘miscarriage
of justice,’ ‘jurisdictional,’ and ‘ineffective assistance’ exceptions to the appeal
13

waivers in his opening brief or otherwise.” (Id. at 2.) The fourth argument raised by
Roscoe is a one substantive claim of his actual innocence: that Roscoe was “actually
innocent of the ACCA enhancement and because the government failed to meet its
burden in proving that there was three qualifying predicate offenses the court lacked
jurisdiction to impose the statutory enhancement.” (Id.) Additionally, Roscoe added
a fifth argument to his petition regarding his claim of “actual innocence” in a Motion
to Take Judicial Notice of the Supreme Court’s Decision in Descamps v. United
States. (See Docs. # 7 & 10.) The government responded to each argument and
argues that Roscoe’s petition (Doc. #1) is due to be dismissed in its entirety. (See
Docs. 5 & 8.)
II. Discussion
A federal prisoner may file a motion to vacate his or her sentence “upon the
ground that the sentence was imposed in violation of the Constitution or laws of the
United States, or that the court was without jurisdiction to impose such sentence, or
that the sentence was in excess of the maximum authorized by law, or is otherwise
subject to collateral attack.” 28 U.S.C. § 2255 ¶ 1. It is well settled that “to obtain
collateral relief, a prisoner must clear a significantly higher hurdle than would exist
on direct appeal.” United States v. Frady, 456 U.S. 152, 166 (1982).

14

A. Roscoe’s Claims of Ineffective Assistance of Counsel Fail.
Ineffective assistance of counsel claims are governed by the standard set forth
in Strickland v. Washington, 466 U.S. 668 (1984). In Strickland, the Supreme Court
established a two-prong test for adjudicating ineffective assistance of counsel claims.
Both prongs of the test must be met for the petitioner to succeed. Id. at 687. First,
Roscoe must show that counsel’s performance was deficient, i.e., outside the range
of professionally competent assistance. Id. The proper measure of an attorney’s
performance is “reasonableness under prevailing professional norms.” Id. at 688.
Unless the petitioner can rebut the “strong presumption that counsel's conduct falls
within the wide range of reasonable professional assistance,” he cannot show that
counsel's performance was constitutionally deficient. Id. at 689. “The test has
nothing to do with what the best lawyers would have done. Nor is the test even what
most good lawyers would have done. [The court asks] only whether some reasonable
lawyer at the trial could have acted, in the circumstances, as defense counsel acted at
trial.” White v. Singletary, 972 F.2d 1218, 1220 (11th Cir. 1992); see also Waters
v. Thomas, 46 F.3d 1506, 1514 (11th Cir. 1995) (stating that “perfection is not the
standard of effective assistance”).5

5

In fact, the Supreme Court has warned against second-guessing professional judgments
made by counsel: “Judicial scrutiny of counsel’s performance must be highly deferential,” and
court should make every effort to “eliminate the distorting effects of hindsight, to reconstruct hte

15

Second, Roscoe must establish prejudice, such that there is a reasonable
probability that, absent counsel’s errors, the outcome of the proceeding would have
been different. Strickland, 466 U.S. at 687; Chandler v. United States, 218 F.3d
1305, 1312-13 (11th Cir. 2000). “A reasonable probability is a probability sufficient
to undermine confidence in the outcome.” Strickland, 466 U.S. at 694. Because the
petitioner must meet both parts of the test, the court does not need to address the
performance prong if the petitioner cannot meet the prejudice prong, and vice versa.
Holladay v. Haley, 209 F.3d 1243, 1248 (11th Cir. 2000).
The Supreme Court has held that Strickland’s two-part test also applies to
“challenges to guilty pleas based on ineffective assistance of counsel.” Hill v.
Lockhart, 474 U.S. 52, 58 (1985). Hill held that to establish prejudice, “the defendant
must show that there is a reasonable probability that, but for counsel’s errors, he
would not have pleaded guilty and would have insisted on going to trial.” Hill, 474
U.S. at 59. The Eleventh Circuit has held that “counsel owes a lesser duty to a client
who pleads guilty than to one who decides to go to trial, and in the former case
counsel need only provide his client with an understanding of the law in relation to
the facts, so that the accused may make an informed and conscious choice between

circumstances of counsel’s challenged conduct, and to evaluate the conduct from counsel’s
perspective at the time.” Strickland, 466 U.S. at 689.

16

accepting the prosecution’s offer and going to trial.” Wofford v. Wainwright, 748
F.2d 1505, 1508 (11th Cir.1984). “To impart such an understanding to the accused,
counsel must, after making an independent examination of the facts, circumstances,
pleadings and laws involved, offer his informed opinion as to the best course to be
followed in protecting the interests of his client.” Id.
1. Roscoe’s Plea was Knowing and Voluntary.
Roscoe contends that he did not knowingly, voluntarily and intelligently agree
to the plea agreement’s waiver provision because Dempsey did not advise him that
the waiver would foreclose an appeal of the ACCA enhancement. (Doc. #1 at 4-5.)
Instead, Roscoe swears that Dempsey told him, as he was executing the plea
agreement, that the waiver provision would not prevent him from appealing the
enhancement.6 (Id. at 5.) Roscoe maintains that had he known he was waiving his
right to appeal the application of the ACCA enhancement, he would have insisted on
going to trial or renegotiated another agreement “that clearly reserved his right to
appeal the ACCA enhancement if applied at sentencing.” (Id. at 7.) He admits that
he “would have most likely received the same exact 15-year sentence had he went to
trial, but would have preserved his right to appeal the ACCA enhancement, and

6

Demsey’s affidavit states that he told Roscoe that there was a chance that the appeal
waiver could bar any appeal of the ACCA enhancement. (Depmsey Aff. ¶ 7.)

17

would have had a chance of winning the case, because you never know what a jury
will do.” (Id. at 8.) (emphasis omitted). He also theorizes that the government would
have agreed to a plea agreement permitting an appeal of an ACCA enhancement.
(Id.)
Dempsey’s alleged incorrect advice does not necessarily amount to ineffective
assistance of counsel under Strickland.

First, Roscoe failed to establish that

Dempsey’s performance was deficient as a matter of law in that his representation did
not fall below an objective standard of reasonableness. Hill, 474 U.S. at 57. As
explained above, in a plea situation, counsel must provide advice “within the range
of competence demanded of attorneys in criminal cases.” Id. at 56–57 (quoting
McMann v. Richardson, 397 U.S. 759, 771 (1970)).

Under this standard,

representation is ineffective only if counsel commits “serious derelictions” of his duty
when advising the accused. Stano v. Dugger, 921 F.2d 1125, 1150–51 (11th Cir.
1991). Absent such blatant errors, however, the court should “indulge a strong
presumption that counsel’s conduct fell within the wide range of reasonably
professional assistance.” Yordan v. Dugger, 909 F.2d 474, 477 (11th Cir. 1990).
Here, the record confirms that Roscoe was well aware of the potential
application of the ACCA enhancement, as well as the waiver provision contained in
the plea agreement. After investigating Roscoe’s case and before any presentation
18

of a plea agreement, Dempsey advised Roscoe that if he was found guilty of the
felon-in-possession charge through a plea or a trial, his criminal history could qualify
him for the ACCA enhancement with a 15 year mandatory minimum prison sentence.
(Roscoe Aff. ¶ 6.) Once the government gave Roscoe a plea agreement, Dempsey
discussed the waiver provision with Roscoe, and although Dempsey claims that he
informed Roscoe that there was a chance it could bar any appeal of the ACCA
enhancement, Roscoe contends that Dempsey told him that he could still appeal the
enhancement. (Id. ¶ 7; Doc. #1 at 5.)
With regard to the plea agreement, Roscoe initialed the portion of the plea
agreement disclosing that he was facing potential application of the enhancement, and
signed and initialed the portion of the plea agreement setting out the waiver. The
waiver did have two exceptions – neither of which clearly set out a specific exception
for an appeal of the ACCA enhancement, although Roscoe contends he was operating
under the misconception that he could. With regard to the plea hearing, the court
expressly informed Roscoe about the existence of the waiver and the potential for a
15-year maximum mandatory sentence. (Plea Transcr. at 6, 8.) Roscoe agreed, under
oath, that the written plea agreement “set forth everything that [he was] relying upon
at this time by way of a plea bargain or plea agreement with the Government.” (Id.
at 6.) Roscoe did not volunteer any understanding that he believed that he could
19

appeal the application of the ACCA enhancement, although the plain language of the
appeal waiver did not include an explicit exception regarding any enhancement. He
also acknowledged that he was not required to plead guilty, but nevertheless wanted
to do so. (Id. at 13.)
Additionally, although Dempsey’s alleged advice regarding the appeal waiver
turned out to be incorrect, that advice was not outside the range of competent advice.
See Hill, 474 U.S. at 56-57. Indeed, even the court opined that the exceptions to the
appeal waiver most likely applied to the application of the ACCA enhancement.
(Sentencing Transcr. at 7-8, 14-15.) However, the Eleventh Circuit disagreed with
this interpretation and held that the appeal waiver applied to the ACCA enhancement.
Dempsey’s incorrect advice did not render his performance deficient as a matter of
law under Strickland.
In the alternative, regardless of whether Dempsey’s performance in advising
Roscoe was deficient, Roscoe cannot show that he was prejudiced under Strickland.
Roscoe’s allegation of prejudice is simply a self-serving, speculative assertions made
with the benefit of 20/20 hindsight. Such allegations are insufficient in this circuit
to establish prejudice under Strickland. See Diaz v. United States, 930 F.2d 832, 835
(11th Cir. 1991). Given Roscoe’s admissions at the plea hearing, his awareness of
the appeal waiver and the potential applicability of the ACCA enhancement, and the
20

risks of going to trial, all of which were discussed with him by Dempsey before he
pled guilty, Roscoe’s after-the-fact allegation of his desire to go to trial, enter a blind
plea, or negotiate a different plea agreement with the government, without more, is
insufficient to establish that but for Dempsey’s alleged advice, he would have not
accepted the plea offer. Id.; see also Cook v. United States, 189 Fed. Appx. 927, 931
(11th Cir. 2006).
2. Dempsey did not operate under a conflict of interest.
Roscoe argues that because Dempsey gave him incorrect advice regarding the
appeal waiver, Dempsey was operating under a conflict of interest when he litigated
Roscoe’s appeal. (Doc. #1 at 10.) To obtain relief on the grounds that his attorney
operated under a conflict of interest, Roscoe must show two things: (1) that his
attorney had an actual conflict of interest and (2) that the conflict “adversely affected”
his attorney’s performance. Pegg v. United States, 253 F.3d 1274, 1277 (11th Cir.
2001). Roscoe failed to establish either element.
First, there is no evidence in the record that Dempsey operated under a conflict
of interest. Roscoe’s premise for his entire conflict of interest argument is based on
the assumption that Dempsey’s performance was somehow deficient. (Doc. #1 at 10.)
However, the court has already found that Dempsey’s performance, although
allegedly not perfect, was not deficient under Strickland. See supra at 18-20. As
21

such his argument that Dempsey somehow operated under a conflict of interest on
appeal necessarily fails. And even if he did, as recounted above, Roscoe was not
“adversely affected” or prejudiced by any alleged deficient performance. See supra
at 20-21.
3. Dempsey did not provide ineffective assistance on appeal.
Roscoe argues that Dempsey was ineffective for not addressing the viability
of the plea agreement’s waiver provision in his opening brief on appeal. (Doc. #1 at
11.) Roscoe contends that this alleged mistake prejudices him by allowing the
government to move “straight away for dismissal.”7 (Id.)

More substantively,

Roscoe also argues that the government did not prove that he had three predicate
felonies needed to qualify him for the ACCA enhancement, and that Dempsey was
deficient by not arguing the “miscarriage-of-justice” and “jurisdictional” exceptions
to the appeal wavier. (Id. at 13-14.) Both arguments fail.
The first argument fails for obvious reasons. Most glaringly, it is totally
speculative whether the Eleventh Circuit would have considered his ACCA argument
on the merits had Dempsey argued that the appeal waiver did not apply in his opening
brief. Dempsey competently argued such in his reply brief, after the government filed

7

He surmises that had Dempsey addressed the waiver in his opening brief, “it is likely
that this alone would have been sufficient to have the petitioner’s ACCA argument heard on its
merits.” (Doc. #1 at 12.)

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its motion to dismiss the appeal based on the waiver. The Eleventh Circuit
necessarily considered this argument and clearly rejected it when it found that the
waiver applied to Roscoe’s appeal of his sentence. The court affords Dempsey’s
performance deference, as an experienced trial and appellate attorney, and indulges
a strong presumption that his performance was reasonable. See Strickland, 466 U.S.
at 689; Chandler, 218 F.3d at 1316. Dempsey’s performance on appeal was not
deficient based upon the order of his arguments.
Even if Dempsey had been deficient in the ordering of the arguments (Which
he was not), Roscoe did not suffer any prejudice. Dempsey argued, at length, that the
appeal waiver did not apply in Roscoe’s reply brief, and the Eleventh Circuit had
ample opportunity to consider the argument. Roscoe’s speculation that the order of
the arguments somehow affected the way the Eleventh Circuit viewed the arguments
is a far cry from the evidence required to establish that he suffered any prejudice.
Roscoe’s second argument similarly fails. Dempsey’s performance on appeal
was not deficient because he failed to argue the “miscarriage-of-justice” and
“jurisdiction” exceptions to the appeal waiver. Any argument that they did apply
would have been meritless. See United States v. Steed, 548 F.3d 961, 979 (11th Cir.
2008); United States v. Bennett, 472 F.3d 825, 833-34 (11th Cir. 2006). Dempsey’s
performance cannot be found deficient for failing to argue a meritless argument.
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Again, even if Dempsey had been deficient in not making these arguments,
Roscoe did not establish that he suffered any prejudice. Roscoe does not dispute the
existence of the youthful-offender adjudication and the marijuana conviction, and he
admitted to those facts for purposes of sentencing. Thus, this argument would not
have invalidated the appeal waiver and Roscoe cannot establish prejudice.
B. Roscoe’s Claim of Actual Innocence Fails.
Roscoe makes two arguments of “actual innocence.” Roscoe argues that the
ACCA enhancement was incorrectly applied to him and that, because the government
did not prove that he committed three predicate offenses that could qualify him for
the enhancement, the court lacked jurisdiction to impose it. (Doc. 1 at 15.) Roscoe
also argues that under Descamps v. United States , 133 S. Ct. 2276 (2013), he is
“actually innocent of the Armed Career Criminal Act” and its 15-year minimum
mandatory sentence because his youthful offender adjudication does not qualify as
an ACCA predicate.8 (Doc. # 7 at 1-4; Doc. #9 at 1-3.) Both arguments fail.

8

In Descamps, the defendant was convicted of possession of a firearm by a convicted
felony and sentenced under the ACCA, based in part upon his prior burglary conviction under
California law. Descamps involved application of the “residual clause” of the ACCA, §
924(e)(2)(B)(ii), which defines “violent felony” as “burglary, arson, or extortion, involves use of
explosives, or otherwise involves conduct that presents a serious potential risk of physical injury
to another.” 18 U.S.C. § 924(e)(2)(B)(ii). The California burglary statute did not include an
element of the generic crime of burglary; it did not require that a burglar “enter or remain
unlawfully in a building.” The Supreme Court held that federal sentencing courts may not apply
the “modified categorical approach” (i.e., consulting a limited class of documents, such as
indictments and jury instructions) to sentencing under ACCA’s “residual clause” when the state

24

To demonstrate actual innocence, a petitioner mut show “factual innocence, not
mere legal insufficiency.” Bousley v. United States, 523 U.S. 614, 623 (1998).
Throughout this entire criminal case, as recounted above, Roscoe has never once
objected to the existence of his youthful-offender adjudication and/or his marijuana
conviction. Instead, he objects to the effect of those convictions with regard to his
ACCA status. His failure to object to their existence equates to an admission of the
convictions. See United States v. Bennett, 472 F.3d 825, 833-34 (11th Cir. 2006);
United States v. Wade, 458 F.3d 1273, 1277 (11th Cir. 2006) (stating “[i]t is the law
of this circuit that a failure to object to allegations of fact in a PSI admits those facts
for sentencing purposes”). Because that admission establishes them as facts, the court
properly used them as predicate offenses during sentencing. Id.
Additionally, Roscoe’s “actual innocence” argument fails because a § 2255
petition is not the “appropriate vehicle for determining whether a conviction later
used to enhance a federal sentence was unconstitutionally obtained.” Daniels v.
United States, 532 U.S. 374, 381 (2001). By the time of sentencing under the ACCA,
a prior conviction that has not been set aside on direct or collateral review is

crime of which the defendant was convicted has a single, indivisible set of elements. 133 S.Ct. at
2281–82.

25

“presumably valid and may be used to enhance the federal sentence.” Id. at 382.
“The presumption of validity that attached to a prior conviction at the time of
sentencing is conclusive, and the defendant may not collaterally attack his prior
conviction though a motion under § 2255.”9 Id. For this separate reason, Roscoe’s
argument fails.
Roscoe’s argument regarding Decamps v. United States is similarly
unpersuasive. Descamps was decided on June 20, 2013, approximately two years
after Roscoe was sentenced by this court. The Supreme Court has unequivocally
stated that “a new rule is not made retroactive to cases on collateral review unless the
Supreme Court holds it to be retroactive.” Tyler v. Cain, 533 U.S. 656, 663 (2001).
The Supreme Court has not declared its decision in Descamps to be retroactively
applicable on collateral review, nor has the court found any cases applying Descamps
retroactively to cases on collateral review. Therefore, the court refuses to do so here.

9

The Daniels court reasoned:
[A] defendant generally has ample opportunity to obtain
constitutional review of a state conviction. But once the “door” to
such review “has been closed,” by the defendant himself — either
because he failed to pursue otherwise available remedies or
because he failed to prove a constitutional violation – the
conviction becomes final and the defendant is not entitled to
another bite at the apple simply because the conviction is later used
to enhance another sentence.

532 U.S. at 383.

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III. Conclusion
For all the foregoing reasons, Roscoe’s Motion (Doc. #1) to Vacate, Set Aside,
or Correct Sentence is due to be denied. A separate order will be entered dismissing
the case in its entirety.
DONE this the 16th

day of October, 2013.

SENIOR UNITED STATES DISTRICT JUDGE

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