USA v. Raymond Malara, III

[DO NOT PUBLISH]
In the
United States Court of Appeals
For the Eleventh Circuit
____________________
No. 22-10856
Non-Argument Calendar
____________________
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
versus
RAYMOND MALARA, III,
Defendant-Appellant.
____________________
Appeal from the United States District Court
for the Middle District of Florida
D.C. Docket No. 8:21-cr-00066-KKM-AAS-1
____________________
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2 Opinion of the Court 22-10856
Before WILSON, B RANCH, and L UCK , Circuit Judges.
PER CURIAM:
Raymond Malara, III, pleaded guilty, pursuant to a written
plea agreement containing a sentence-appeal waiver, to one count
of possession with the intent to distribute cocaine, fentanyl, and
marijuana, in violation of 21 U.S.C. §§ 841(a)(1), 841(b)(1)(C). The
district court sentenced him to 108 months’ imprisonment and 36
months’ supervised release. On appeal, he argues that his trial
counsel was ineffective for failing to raise a relevant conduct
objection at sentencing when the district court held him
accountable for 111.6 grams of methamphetamine sold to a co-
conspirator.1
1 As part of the plea agreement, Malara admitted to the following facts.
Between October 2020, and February 2021, law enforcement agents
intercepted calls between Malara and several co-conspirators on authorized
wiretaps, during which Malara and others discussed the purchase, distribution,
and sale of controlled substances. From the intercepted calls, agents identified
Malara as a cocaine trafficker. When officers searched his apartment, they
found a large quantity of cash, 250 grams of cocaine, and 396 grams of
marijuana. They also searched a BMW parked outside the residence and
found between 100-200 fentanyl pills, and approximately 4 kilograms of
marijuana. In addition to describing the above offense conduct that Malara
admitted to in the plea agreement, his presentence investigation report (“PSI”)
also stated that he was accountable for 111.6 grams of methamphetamine (aka
“Ice”) sold to a co-conspirator on January 5, 2021. Malara objected, arguing
that the Ice substance was “exotic marijuana,” not methamphetamine.
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22-10856 Opinion of the Court 3
In response, the government has moved to dismiss Malara’s
appeal based on the sentence-appeal waiver, arguing that Malara is
recasting a sentencing challenge as an ineffective-assistance claim
in order to avoid the valid sentence-appeal waiver. Alternatively,
the government argues that we should not address the ineffective-
assistance claim on direct appeal because it was not raised before
the district court and the factual record is not developed. Malara
responds that the sentence-appeal waiver does not encompass
ineffective-assistance claims, and it does not bar the instant appeal.
After review, we conclude that the sentence-appeal waiver
is valid and enforceable. To the extent Malara challenges the
district court’s application of the sentencing guidelines, his claim is
barred by the appeal waiver. We decline to address his ineffective-
assistance claim on direct appeal. Therefore, we grant the
government’s motion to dismiss.
“We review the validity of a sentence appeal waiver de
novo.”
United States v. Johnson, 541 F.3d 1064, 1066 (11th Cir.
2008). We enforce appeal waivers that are made knowingly and
voluntarily.
See United States v. Bascomb, 451 F.3d 1292, 1294
(11th Cir. 2006);
United States v. Bushert, 997 F.2d 1343, 1350–51
(11th Cir. 1993). To demonstrate that a waiver was made
knowingly and voluntarily, the government must show that either
(1) the district court specifically questioned the defendant about the
However, he did not raise a relevant conduct objection to the finding holding
him accountable for the methamphetamine.
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4 Opinion of the Court 22-10856
waiver during the plea colloquy; or (2) the record makes clear that
the defendant otherwise understood the full significance of the
waiver.
Bushert, 997 F.2d at 1351.
Malara’s plea agreement contained the following waiver:
The defendant agrees that this Court has jurisdiction
and authority to impose any sentence up to the
statutory maximum and expressly waives the right to
appeal defendant’s sentence on any ground, including
the ground that the Court erred in determining the
applicable guidelines range pursuant to the United
States Sentencing Guidelines, except (a) the ground
that the sentence exceeds the defendant’s 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 to the
Constitution; provided, however, that if the
government exercises its right to appeal the sentence
imposed, as authorized by 18 U.S.C. § 3742(b), then
the defendant is released from his waiver and may
appeal the sentence as authorized by 18 U.S.C.
§ 3742(a).
(emphasis in original). Malara signed the plea agreement and
initialed each page.
The record establishes that, at the change-of-plea hearing,
the magistrate judge questioned Malara about the sentence-appeal
waiver and the four limited grounds under which he could appeal
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22-10856 Opinion of the Court 5
notwithstanding the waiver. Malara stated that he understood and
that he was entering the waiver freely and voluntarily.2 The
magistrate judge recommended that the district court accept
Malara’s guilty plea, which the district court did. Accordingly, the
record establishes that Malara’s sentence-appeal waiver was
knowingly and voluntarily made and is enforceable.
Bushert, 997
F.2d at 1351;
see also United States v. Weaver, 275 F.3d 1320, 1333
(11th Cir. 2001) (enforcing an appeal waiver where “the waiver
provision was referenced during [the defendant’s] Rule 11 plea
colloquy and [the defendant] agreed that she understood the
provision and that she entered into it freely and voluntarily”).
Indeed, Malara does not contest the validity of the waiver. Instead,
he argues that it did not encompass a waiver of his right to raise a
Sixth Amendment ineffective-assistance-of-counsel claim. Malara’s
argument is unpersuasive.
Where a valid appeal waiver exists, a defendant may not
“circumvent the terms of the sentence-appeal waiver simply by
recasting a challenge to his sentence as a claim of ineffective
assistance, thus rendering the waiver meaningless.”
Williams v.
United States, 396 F.3d 1340, 1342 (11th Cir. 2005). Moreover, we
generally do not consider ineffective-assistance-of-counsel claims
on direct appeal.
United States v. Bender, 290 F.3d 1279, 1284 (11th
Cir. 2002);
see also United States v. Puentes-Hurtado, 794 F.3d
1278, 1285 (11th Cir. 2015) (holding that a claim that counsel’s
2 Malara consented to the magistrate judge conducting the plea proceeding.
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6 Opinion of the Court 22-10856
ineffective assistance rendered a guilty plea involuntary was not
barred by an appeal waiver but declining to reach the merits of the
claim on direct appeal). Rather, the preferred method for raising
ineffective-assistance-of-counsel claims is in a motion to vacate
sentence under 28 U.S.C. § 2255, which affords the district court
the chance to develop the facts necessary to determine the
adequacy of representation.
Massaro v. United States, 538 U.S. 500,
504–05 (2003).
Here, Malara argues that his counsel was ineffective for
failing to raise a relevant conduct objection to the 111.6 grams of
methamphetamine attributed to him. He maintains that the
distribution of the methamphetamine was not relevant conduct for
which he could be held accountable and, had counsel objected on
this ground, there is a reasonable probability that he would have
received a lesser sentence. Although Malara argues that his claim
is not waived because the appeal waiver does not apply to claims
of ineffective assistance of counsel, the government’s point that
Malara has repackaged a sentencing challenge under the guise of
an ineffective-assistance claim in an attempt to circumvent the
appeal waiver is well taken. Thus, to the extent that Malara argues
that the methamphetamine was not relevant conduct, his claim is
barred by his valid and enforceable sentence-appeal waiver.
As for Malara’s ineffective-assistance claim, we decline to
consider the merits of this argument on direct appeal because it was
not raised before the district court and the record is not developed
enough to assess the adequacy of counsel’s representation.
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22-10856 Opinion of the Court 7
Massaro, 538 U.S. at 504–05;
Bender, 290 F.3d at 1284 (“We will not
generally consider claims of ineffective assistance of counsel raised
on direct appeal where the district court did not entertain the claim
nor develop a factual record.”). Malara is free to bring this
ineffective assistance claim anew in a § 2255 proceeding.3
Accordingly, we GRANT the government’s motion to dismiss.
DISMISSED.
3 We express no opinion as to whether the sentence-appeal waiver would
otherwise bar claims of ineffective assistance at sentencing. That issue—if
raised by the government in a § 2255 proceeding—is for the district court to
address in the first instance.
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