USA v. Damien Deshaun Dennis

[DO NOT PUBLISH]
In the
United States Court of Appeals
For the Eleventh Circuit
____________________
No. 22-14109
Non-Argument Calendar
____________________
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
versus
DAMIEN DESHAUN DENNIS,
Defendant-Appellant.
____________________
Appeal from the United States District Court
for the Middle District of Florida
D.C. Docket No. 3:22-cr-00011-TJC-JBT-1
____________________
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2 Opinion of the Court 22-14109
Before JILL PRYOR , BRANCH, and A BUDU , Circuit Judges.
PER CURIAM:
This case is before us on the government’s motion to dismiss
Damien Dennis’s direct appeal based on the sentence appeal waiver
within his plea agreement. Upon review of the record, we grant
the government’s motion.
I. FACTUAL BACKGROUND & PROCEDURAL
HISTORY
In February 2022, a federal grand jury indicted Dennis on
two counts of bank fraud, in violation of 18 U.S.C. § 1344 (Counts
1 and 2), two counts of falsely representing a social security num-
ber, in violation of 42 U.S.C. § 408(a)(7)(B) (Counts 3 and 4), and
two counts of aggravated identity theft, in violation of 18 U.S.C.
§ 1028A(a)(1) (Counts 5 and 6). Shortly thereafter, he entered into
a written plea agreement with the government in which he agreed
to plead guilty to Counts 1 and 5 in exchange for the government
dismissing the remaining counts. In the agreement, the govern-
ment stated that it intended to move for an upward variance at sen-
tencing. Dennis agreed that, should the court accept the recom-
mendation, he could not withdraw his plea.
The agreement included a section entitled “Defendant’s
Waiver of Right to Appeal Sentence,” which explained that, upon
entering the plea agreement, Dennis waived his right to appeal his
sentence “on any ground, including the ground that the Court
erred in determining the applicable guidelines range pursuant to
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22-14109 Opinion of the Court 3
the United States Sentencing Guidelines.” Dennis reserved the
right to appeal on “(a) the ground that the sentence exceeds [his]
applicable guidelines range as determined by the Court pursuant
to the United States Sentencing Guidelines; (b) the ground that the
sentence exceeds the statutory maximum penalty; or (c) the
ground that the sentence violates the Eighth Amendment.” (em-
phasis in original). Additionally, the agreement provided an excep-
tion if “the government exercise[d] its right to appeal the sentence
imposed.” Dennis initialed each page and signed the final page.
As part of the plea agreement, Dennis signed a statement
which detailed the facts supporting the agreement. He also signed
a form consenting to the magistrate judge conducting his plea hear-
ing.
At his change-of-plea hearing, the magistrate judge placed
Dennis under oath and advised him that the government could use
any false statement by him in a perjury prosecution. The magis-
trate judge advised Dennis of his right to have the district court
take his plea, and Dennis again consented to having the magistrate
judge take his plea. Dennis testified that his highest level of educa-
tion was the eleventh grade, and that he spoke, read, and under-
stood English. He stated that he had not taken any medication or
intoxicants that would affect his ability to understand the proceed-
ings and, while he had been treated for paranoid schizophrenia
from 2015 through 2017, he was not currently suffering from any
mental or emotional disease. Dennis’s attorney indicated that he
had no concerns regarding Dennis’s competency to enter a plea.
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4 Opinion of the Court 22-14109
The magistrate judge advised Dennis of the trial rights he
would be waving by pleading guilty, including the ability to poten-
tially challenge on appeal any rulings the court made in his case.
The magistrate judge also advised that Dennis could lose certain
civil rights by pleading guilty, such as his right to vote, hold public
office, serve on juries, and own and possess firearms and ammuni-
tion. Dennis confirmed that he understood the waivers he was
making and the potential consequences of entering the plea.
Regarding sentencing, the magistrate judge advised Dennis
that the district court would calculate the applicable sentencing
guideline range and consider several sentencing factors to deter-
mine a reasonable sentence. The magistrate judge noted that,
while the guideline range and any recommended sentence by the
government would not bind the district court, the statutory mini-
mums and maximums would. Dennis confirmed that he under-
stood the terms of the plea agreement and had discussed them
with his attorney, and that he understood he would be bound by
his plea, even if the sentence was higher than he expected.
Dennis confirmed that he had received, read, and reviewed
the indictment with his attorney. The magistrate judge outlined
the charges Dennis was pleading guilty to and the elements the
government would have to prove as to both counts. Dennis con-
firmed that he understood the charges and their elements and did
not have any questions.
The magistrate judge also advised Dennis that he faced sev-
eral penalties by pleading guilty, including a maximum prison
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22-14109 Opinion of the Court 5
sentence of 30 years as to Count 1, followed by no more than 5
years’ supervised release. The magistrate judge further noted that
Count 5 carried a mandatory minimum two-year sentence, to run
consecutively with any other term of imprisonment, followed by a
maximum of one year of supervised release. The magistrate judge
stated that the cumulative maximum penalties for both counts
were 32 years’ imprisonment, a $1,250,000 fine, a 5-year term of
supervised release, and a $200 special assessment. The parties
agreed that the magistrate judge accurately stated the maximum
and minimum penalties, and Dennis stated that he understood, had
discussed these penalties with his attorney, and did not have any
questions.
Regarding the plea agreement, Dennis confirmed that he
had read it, discussed it with his attorney, signed it, and understood
it. The magistrate judge advised Dennis that the government
agreed to dismiss the remaining counts in the indictment, but that
the district court could consider relevant evidence giving rise to
those charges in computing his guideline range. The magistrate
judge further advised Dennis that the agreement indicated that the
government would seek an upward variance, but that the district
court would not be bound by that request. The magistrate judge
also advised Dennis that the plea agreement contained a sentence
appeal waiver, which would waive his right to appeal his sentence
except in four specific circumstances: (1) the sentence exceeded his
guideline range as calculated by the court; (2) the sentence ex-
ceeded the statutory maximum; (3) the sentence violated the
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6 Opinion of the Court 22-14109
Eighth Amendment; or (4) the government appealed the sentence.
Dennis stated that he understood.
Dennis pled guilty to Counts 1 and 5, stated that he under-
stood the factual proffer, and admitted that the facts were true.
Thus, the magistrate judge found that sufficient facts supported the
guilty plea. Dennis stated that he had not received any promises or
assurances not reflected in the plea agreement, he was satisfied
with his attorney’s representation, and he was not forced, threat-
ened, coerced, or intimidated into pleading guilty. The magistrate
judge found that Dennis’s decision to plead guilty was made know-
ingly, freely, intelligently, and voluntarily, and stated that it would
recommend that the district court accept his plea. The magistrate
judge later issued a report and recommendation (“R&R”) recom-
mending the district court accept Dennis’s guilty plea, and Dennis
was advised that he had fourteen days to object to the R&R. The
district court ultimately accepted the guilty plea.
Dennis’s presentence investigation report (“PSI”) calculated
his base offense level as 7 under U.S.S.G. § 2B1.1(a)(1), and added 4
levels under U.S.S.G. § 2B1.1(b)(1)(C) because the loss was $20,000,
added 2 levels under § 2B1.1(b)(11)(B) because the offense involved
a counterfeit driver’s license, and then subtracted 2 levels for ac-
ceptance of responsibility under § 3E1.1(a), resulting in a total of-
fense level of 11. The PSI calculated his criminal history category
at V, which, combined with a total offense level of 11, resulted in a
guideline sentencing range of 24 to 30 months’ imprisonment for
Count 1 and a consecutive term of imprisonment of 24 months for
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22-14109 Opinion of the Court 7
Count 5. The PSI stated that the statutory maximum term of im-
prisonment for Count 1 was 30 years and a consecutive term of 2
years’ imprisonment for Count 5.
At sentencing, the district court asked Dennis if he had ob-
jections to the PSI, and Dennis noted that his prior objections had
been resolved. The district court then adopted the PSI guideline
calculations. Next, the government addressed the court, arguing
for an upward variance due to Dennis’s extensive criminal history,
high potential of recidivism, the seriousness of his offense, and the
need for deterrence. The government requested the district court
impose a 12-year total sentence. Dennis opposed the government’s
arguments and requested a within guideline sentence.
The district court granted the government’s motion for an
upward variance based on the 18 U.S.C. § 3553(a) factors and sen-
tenced him to: (1) a 120-month term for Count 1 to run consecu-
tively with a 24-month term for Count 5; (2) a 5-year term of su-
pervised release for Count 1 to run concurrently with a 1-year term
for Count 5; (3) $20,000 in restitution; and (4) $200 in special assess-
ments. The court stated that, “[i]n addition to the standard condi-
tions,” it was imposing the following conditions of supervised re-
lease: (1) participation in a substance abuse program; (2) participa-
tion in a mental health treatment program; (3) that he would “be
subject to a search condition”; (4) prohibition from incurring new
credit or obligating himself to major purchases without approval;
and (5) that he would have to provide financial information to the
probation officer upon request. The court further required Dennis
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8 Opinion of the Court 22-14109
to submit to DNA collection and periodic drug testing. The district
court asked if either party objected to the sentence, and neither
party objected. The court noted that Dennis had fourteen days to
appeal and that he was entitled to counsel.
The district court entered judgment reflecting its sentence,
including the five additional conditions of supervised release that
the court pronounced at sentencing. The judgment also listed thir-
teen “standard” conditions of supervised release.
After Dennis filed his notice of appeal, his counsel filed a
motion to withdraw, and Dennis was appointed new counsel on
appeal. Appointed counsel filed an Anders1 motion and brief, as-
serting that there were no non-frivolous issues for appeal. A panel
of this Court denied the Anders motion and ordered merits briefing
as to whether the district court erroneously failed to pronounce the
standard conditions of supervised release at Dennis’s sentencing
hearing. Now, the government moves to dismiss Dennis’s appeal
due to the appeal waiver in his plea agreement.
II. ANALYSIS
We do not review issues a party fails to raise in their initial
brief. United States v. Sperrazza, 804 F.3d 1113, 1125 (11th Cir. 2015).
We review de novo a sentence appeal waiver’s validity. United States
v. Johnson, 541 F.3d 1064, 1066 (11th Cir. 2008). A sentence appeal
waiver is enforceable if it was made knowingly and voluntarily. Id.
To establish that the waiver was made knowingly and voluntarily,
1 Anders v. California, 386 U.S. 738 (1967).
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22-14109 Opinion of the Court 9
the government must show either that: “(1) the district court spe-
cifically questioned the defendant about the waiver; or (2) the rec-
ord makes clear that the defendant otherwise understood the full
significance of the waiver.” Id. (citing United States v. Bushert, 997
F.2d 1343, 1351 (11th Cir. 1993)).
“[T]he touchstone for assessing” whether a defendant en-
tered a waiver knowingly and voluntarily is whether the district
court “clearly conveyed to the defendant that he was giving up his
right to appeal under most circumstances.” United States v. Boyd,
975 F.3d 1185, 1192 (11th Cir. 2020) (brackets and emphasis omit-
ted) (quoting Bushert, 997 F.2d at 1352-53). An appeal waiver may
waive “the right to appeal difficult or debatable legal issues or even
blatant error.” Id. at 1191 n.5 (internal quotation marks omitted).
Further, even “a vigorous dispute about an issue during the sen-
tencing proceedings does not preserve that issue for appeal when
the terms of the appeal waiver do not except it from the waiver.”
United States v. Bascomb, 451 F.3d 1292, 1296 (11th Cir. 2006).
However, a sentence appeal waiver does not completely bar
appellate review because review may be available despite a valid
appeal waiver when the defendant was “sentenced entirely at the
whim of the district court,” above the statutory maximum, or
based on a constitutionally impermissible factor. Johnson, 541 F.3d
at 1068 (internal quotation marks omitted). We have also noted
that extreme circumstances, “for instance, if the district court had
sentenced [the defendant] to a public flogging,” may implicate due
process and require that the defendant be allowed to appeal despite
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10 Opinion of the Court 22-14109
a valid appeal waiver. Id. (internal quotation marks omitted). Nev-
ertheless, a defendant is “free to bargain away his right to raise con-
stitutional issues” on appeal. Bascomb, 451 F.3d at 1297.
Dennis argues that the district court violated his Fifth
Amendment right to due process by failing to inform him at his
sentencing hearing that he would also be subjected to thirteen
“standard” conditions of supervised release, and by failing to make
an individualized assessment as to whether those conditions were
necessary. Notably, he does not argue that his sentence exceeded
the guideline range as calculated by the court, exceeded the statu-
tory maximum, or violated the Eighth Amendment. In response,
the government contends that, in his plea agreement, Dennis
waived the right to raise this argument on appeal.
We grant the government’s motion to dismiss. The record
shows that Dennis knowingly and voluntarily entered into the ap-
peal waiver contained within his plea agreement, and none of his
arguments fall within the narrow exceptions that would allow him
to appeal. The magistrate judge, with Dennis’s consent, accepted
the guilty plea and thoroughly explained to Dennis the conse-
quences of entering the plea, including the appeal waiver. Dennis’s
responses clearly indicated that he understood the appeal wavier
and intended to enter into the plea agreement. Johnson, 541 F.3d at
1066; Boyd, 975 F.3d at 1192. Although Dennis arguably preserved
the right to appeal his sentence as being above the guideline rage
calculated in the PSI, he does not raise that issue in his appeal, and
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22-14109 Opinion of the Court 11
we will not consider it sua sponte. Sperrazza, 804 F.3d at 1125. As
such, Dennis’s appeal waiver is valid and enforceable.
III. CONCLUSION
For the reasons set forth above, we GRANT the govern-
ment’s motion to dismiss Dennis’s appeal.
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