UNPUBLISHED

UNITED STATES COURT OF APPEALS

FOR THE FOURTH CIRCUIT

No. 11-4649

UNITED STATES OF AMERICA,

Plaintiff - Appellee,

v.

DERRICK ALAN MCCASKEY,

Defendant - Appellant.

Appeal from the United States District Court for the Eastern 

District of North Carolina, at Raleigh. Terrence W. Boyle, 

District Judge. (2:10-cr-00016-BO-1)

Argued: January 30, 2013 Decided: April 5, 2013

Before TRAXLER, Chief Judge, and GREGORY and DUNCAN, Circuit 

Judges.

Affirmed in part; vacated in part by unpublished opinion. 

Judge Gregory wrote the opinion, in which Chief Judge Traxler

and Judge Duncan joined.

ARGUED: Neal Gary Rosensweig, NEAL ROSENSWEIG, P.A., Hollywood, 

Florida, for Appellant. Yvonne Victoria Watford-McKinney, 

OFFICE OF THE UNITED STATES ATTORNEY, Raleigh, North Carolina, 

for Appellee. ON BRIEF: Thomas G. Walker, United States 

Attorney, Jennifer P. May-Parker, Assistant United States 

Attorney, OFFICE OF THE UNITED STATES ATTORNEY, Raleigh, North 

Carolina, for Appellee.
2

Unpublished opinions are not binding precedent in this circuit.
3

GREGORY, Circuit Judge:

Derrick Alan McCaskey received a combined sentence of 200 

months’ imprisonment following his guilty plea to one count of 

conspiracy and possession with intent to distribute drugs, in 

violation of 21 U.S.C. § 846, and one count of being a felon in 

possession of a firearm, in violation of 18 U.S.C. § 922. On 

appeal, McCaskey challenges the district court’s compliance with 

the requirements of Federal Rule of Criminal Procedure 11, and 

notwithstanding the presence of an appeal waiver, asks us to 

consider the reasonableness of his sentence. For the reasons 

that follow, we affirm in part and vacate in part McCaskey’s 

conviction and sentence.

I.

A.

As a result of extensive drug-related criminal activities, 

McCaskey was charged with multiple counts in a fifteen-count 

multi-defendant superseding indictment. Pursuant to a written 

plea agreement, McCaskey pled guilty to two counts--Count One, 

which charged him with conspiracy, and possession with intent, 

to distribute drugs, in violation of 21 U.S.C. § 846;1 and Count 

 1 McCaskey was held accountable for a drug amount with a 

total marijuana equivalency of 8,556 kilograms. The actual 

drugs consist of cocaine base (crack), dihydrocodeinone 

(Continued)
4

Fourteen, which charged him with being a felon in possession of 

a firearm, in violation of 18 U.S.C. § 922. In turn, the 

Government agreed to dismiss six other drug charges against 

McCaskey. The written plea agreement contained an express 

waiver of McCaskey’s right to appeal the sentence imposed by the 

district court.2

At the plea hearing required by Rule 11, McCaskey was 

represented by counsel, and informed the court that he discussed 

his case with his counsel and was satisfied with his counsel’s 

representation. McCaskey told the court that he was 22 years 

old and had obtained a GED. The district court confirmed that 

McCaskey had read the plea agreement and had spoken with his 

 

(Vicodin), 3,4-methylenedioxymethamphetamine (MDMA or ecstasy), 

and marijuana.

2 The waiver provision in the plea agreement states:

The Defendant agrees . . . [t]o waive all rights 

conferred by 18 U.S.C. § 3742 to appeal whatever 

sentence is imposed, including any issues that 

relate to the establishment of the advisory 

Guideline range, reserving only the right to 

appeal from a sentence in excess of the 

applicable advisory Guideline range that is 

established at sentencing, and further waive all 

rights to contest the conviction or sentence in 

any post-conviction proceeding, including one 

pursuant to 28 U.S.C. § 2255, excepting an appeal 

or motion based upon grounds of ineffective 

assistance of counsel or prosecutorial misconduct 

not known to the Defendant at the time of the 

Defendant’s guilty plea.
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counsel about the agreement. The court summarized the charges 

in the superseding indictment and the maximum penalties for each 

count. The court also summarized the terms of the plea 

agreement and advised McCaskey of the rights he would forfeit by 

pleading guilty--the right to have his case tried by a jury, the 

right at trial to confront and cross-examine the witnesses 

against him, and the waiver of these rights if the court accepts 

the plea. McCaskey responded that he understood he was giving 

up these rights. McCaskey denied that “anyone threatened [him] 

or forced [him] to [plead guilty],” and affirmed that he was 

“voluntarily” pleading guilty. The district court did not

expressly ascertain whether McCaskey understood the implications 

of the appeal waiver in the plea agreement. The court heard 

from the Government the facts supporting Counts One and 

Fourteen, found that there was a factual basis for the plea, and 

that the plea was voluntary. Consequently, the court accepted 

McCaskey’s plea as to Counts One and Fourteen, and dismissed the 

other charges against him.

Subsequently, a presentence investigation report was 

prepared which calculated McCaskey’s applicable Sentencing 

Guidelines range based on a total offense level of 33 and a 

criminal history category of VI as 188 to 235 months’ 

imprisonment, with a statutory maximum of 120 months on Count 

Fourteen. At the sentencing hearing, the district court
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sentenced McCaskey to a total term of imprisonment of 200 months 

consisting of 200 months’ imprisonment on Count One and a 

concurrent 120-month sentence on Count Fourteen.

B.

McCaskey timely appealed arguing that: (1) his plea was 

not intelligent, knowing, and voluntary because the district 

court failed to comply with the procedural requirements of Rule

11, and in tandem, the appeal waiver in the plea agreement is 

unenforceable; and (2) that his total 200-month sentence is 

unreasonable. The Government moved to dismiss the appeal, 

arguing that McCaskey’s plea was knowing and voluntary and his 

sentencing challenge fell within the scope of the waiver of his 

right to appeal contained in the plea agreement.

McCaskey filed an opposition to the motion to dismiss and 

moved to file a supplemental brief. He argued that the record 

failed to establish that he had previously been convicted for a 

crime punishable by a term of imprisonment of more than one 

year. Consequently, McCaskey argued, in light of our recent 

decision in United States v. Simmons, 649 F.3d 237 (4th Cir. 

2011) (en banc), he could not have been convicted of being a 

felon in possession of a firearm. He asserted the guilty plea 

was invalid and that the waiver did not bar his appeal. The 

Government did not oppose the request for supplemental briefing.
7

We granted leave to file the supplemental brief, but 

deferred ruling on the Government’s motion to dismiss, directing 

the Government to respond to the merits of the appeal. In the 

Government’s response on the merits, it repeated its arguments 

in the motion to dismiss, but conceded that pursuant to Simmons, 

McCaskey’s conviction and sentence as to Count Fourteen must be 

vacated. We now reach the merits of the appeal and have 

jurisdiction pursuant to 28 U.S.C. § 1291.

II.

We first address the adequacy of the Rule 11 hearing, then 

we turn to the enforceability of the appeal waiver, and lastly, 

in light of the Government’s concession, we consider the merits 

of the appeal as to Count Fourteen. Since McCaskey did not seek 

to withdraw his guilty plea in the district court, he did not 

preserve the errors as to the adequacy of the Rule 11 hearing 

and the enforceability of the plea waiver, thus our review is 

for plain error. United States v. Hairston, 522 F.3d 336, 341 

(4th Cir. 2008); United States v. Martinez, 277 F.3d 517, 527 

(4th Cir. 2002). To satisfy the plain error standard, McCaskey 

must show: (1) an error occurred; (2) the error was plain; and 

(3) the error affected his substantial rights. See United 

States v. Olano, 507 U.S. 725, 732 (1993). In addition, we need 

not exercise discretion to correct the error “unless the error 
8

seriously affects the fairness, integrity or public reputation 

of judicial proceedings.” Id. (internal quotation marks and 

alterations omitted).

A.

At a required Rule 11 hearing, the district court must 

“inform the defendant of, and ensure that he understands, the 

nature of the charges against him and the consequences of his 

guilty plea.” Hairston, 522 F.3d at 340 (citing United States 

v. Damon, 191 F.3d 561, 564 (4th Cir. 1999)). To ensure a plea 

is voluntary, a district court “must address the defendant 

personally in open court and determine that the plea is 

voluntary and did not result from force, threats, or promises 

(other than promises in a plea agreement).” Fed. R. Crim. P. 

11(b)(2). Among other things, the district court must advise 

and question the defendant regarding his right to a jury trial, 

right to confront the witnesses against him, the nature of each 

charge to which the defendant is pleading, and any maximum 

penalty the defendant faces. Fed. R. Crim. P. 11(b).

Applying these principles, upon review of the totality of 

the circumstances in the record, we conclude that the district

court substantially complied with the requirements of Rule 11,

and McCaskey knowingly and voluntarily pled guilty to Counts One 

and Fourteen of the superseding indictment. McCaskey contends 

otherwise, arguing that the district court failed to: mention 
9

the waiver of his right to have a jury determine the existence 

and applicability of his prior convictions; inform him that any 

estimate of his sentence is not binding; advise him the court 

would take the advisory guidelines into account; and apprise him 

that relevant conduct would be considered in determining his 

sentence. Even assuming the district court erred by failing to 

act as McCaskey specifies, the court’s omissions did not affect 

McCaskey’s substantial rights because under the state of the law 

at the time of the hearing, the record supports McCaskey’s

convictions for Counts One and Fourteen.

McCaskey makes much of the fact that had the district court 

complied with his version of the requirements of Rule 11, he 

would not have pled guilty to Count Fourteen, a charge for which 

he could not presently be convicted. McCaskey overlooks the 

fact that at the time of the hearing, when McCaskey pled guilty 

to being a felon in possession of a firearm, there was no 

indication that the facts did not support the conviction. The 

district court operated in a pre-Simmons world, where under 

United States v. Harp, 406 F.3d 242, 246 (4th Cir. 2005), a 

federal defendant could be convicted of being a felon in 

possession of a firearm, even though none of his prior state 

convictions amounted to a “felony”--a crime punishable by more 

than one year imprisonment. Thus, at the time, even if the 

district court’s compliance with Rule 11 was defunct, the 
10

omissions did not affect McCaskey’s substantial rights because 

under the then state of the law, he could have been convicted of

being a felon in possession of a firearm. Accordingly, we 

conclude that based on the totality of the circumstances, even 

assuming the district court failed to comply with the 

requirements of Rule 11, the omissions did not affect McCaskey’s 

substantial rights and his plea was entered voluntarily.

B.

We also find that McCaskey knowingly and voluntarily waived 

his right to appeal the sentence imposed. We have held that an 

appeal “waiver is not knowingly or voluntarily made if the 

district court fails to specifically question the defendant 

concerning the waiver provision of the plea agreement during the 

Rule 11 colloquy and the record indicates that the defendant did 

not otherwise understand the full significance of the waiver.” 

United States v. Marin, 961 F.2d 493, 496 (4th Cir. 1992)

(citation omitted). The validity of a waiver is “‘evaluated by 

reference to the totality of circumstances.’” United States v. 

Blick, 408 F.3d 162, 169 (4th Cir. 2005) (quoting United States 

v. General, 278 F.3d 389, 400 (4th Cir. 2002). If the waiver is 

knowing and intelligent, and the issue on appeal falls within 

the scope of the waiver, we will enforce the waiver. United 

States v. Pointdexter, 492 F.3d 263, 270 (4th Cir. 2007).
11

The record indicates that the district court failed to 

inquire expressly whether McCaskey understood the waiver 

provision. Nonetheless, we find that McCaskey fully understood 

the significance of the waiver. At the time of the plea 

hearing, McCaskey was a 22-year old with a GED. He informed the 

district court that he was able to read, write, speak and 

understand English. The written plea agreement as a whole, and 

particularly the appeal waiver, is clear. McCaskey and his 

counsel signed the written agreement acknowledging that he 

understood the terms of the plea and informed the district court 

that he understood the rights he was giving up. Thus, although 

the district court failed to inquire as to McCaskey’s 

comprehension of the waiver, because we find that McCaskey fully 

understood the consequences of the waiver, and there is no 

indication that McCaskey would not have pled otherwise, we find 

that the error did not affect his substantial rights.

Accordingly, the appeal waiver is valid.

McCaskey’s challenge to the reasonableness of his sentence 

falls within the scope of the valid appeal waiver. In his plea 

agreement, McCaskey waived his right to appeal any sentence 

imposed by the district court that fell within the applicable 

guideline range. McCaskey’s 200-month sentence on Count One

falls within his advisory guideline range of 188 to 235 months’ 

imprisonment, and the concurrent 120-month sentence on Count 
12

Fourteen is the statutory maximum sentence. As McCaskey’s 

sentence falls within the applicable guideline range, we hold 

that McCaskey waived his right to appeal the reasonableness of 

his sentence.

C.

Notwithstanding the validity of the plea and enforceability 

of the appeal waiver, the Government seeks to enforce the appeal 

waiver selectively, conceding that Count Fourteen must be 

vacated, but seeking enforcement of the appeal waiver on Count 

One. We believe the Government can so proceed. See United 

States v. Brock, 211 F.3d 88, 90 n.1, 92 n.6 (4th Cir. 2000) 

(reviewing an argument that fell within the scope of a waiver, 

but refraining from reviewing another argument which also fell 

within the waiver because the Government sought enforcement as 

to the latter but not the former argument). In light of the 

Government’s posture, we turn to the merits of the appeal of 

Count Fourteen.

Although the Government concedes that McCaskey’s conviction 

and sentence must be vacated in light of our decision in 

Simmons, 649 F.3d 237, this concession does not necessarily end 

our inquiry, as we must satisfy ourselves that vacatur is 

warranted. See United States v. Rodriguez, 433 F.3d 411, 414 

n.6 (4th Cir. 2006).
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To qualify as a predicate offense under 18 U.S.C. § 922(g), 

for being a felon in possession of a firearm, the prior 

conviction must have been “punishable by imprisonment for a term 

exceeding one year.” 18 U.S.C. § 922(g). The predicate 

offenses for McCaskey’s firearm count arise from a consolidated 

sentence of 6 to 8 months that McCaskey received in 2006 on 

three North Carolina convictions--breaking and entering a motor 

vehicle, possession with intent to sell and deliver marijuana, 

and manufacturing marijuana, in violation of North Carolina 

General Statutes §§ 14-56, 90-95. As stated in McCaskey’s 2006 

Judgment and Commitment, each of these offenses are Class I 

felonies, and because McCaskey was sentenced within the 

presumptive range, the maximum sentence he could have received 

was 8 months’ imprisonment. Because the prior convictions fail 

to qualify as a prior felony for purposes of being a felon in 

possession of a firearm, we vacate McCaskey’s conviction and 

sentence on Count Fourteen. We note that McCaskey’s 200-month 

sentence on Count One is unaffected by this disposition because 

his 120-month sentence on Count Fourteen was to run concurrently 

with the sentence on Count One.

III.

For the reasons stated above, we grant in part the 

Government’s motion to dismiss the appeal as it relates to Count 
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One, but deny it as to Count Fourteen. Additionally, we affirm 

McCaskey’s sentence on Count One, but vacate his conviction and 

sentence as to Count Fourteen.

AFFIRMED IN PART;

VACATED IN PART