 United States Court of Appeals
         FOR THE DISTRICT OF COLUMBIA CIRCUIT



Argued January 22, 2018               Decided March 23, 2018

                        No. 17-3012

                UNITED STATES OF AMERICA,
                        APPELLEE

                              v.

                       JAMES POWERS,
                         APPELLANT


        Appeal from the United States District Court
                for the District of Columbia
                   (No. 1:16-cr-00076-1)


    Robert S. Becker, appointed by the court, argued the cause
and filed the briefs for appellant.

     Rachel Heron, Attorney, U.S. Department of Justice,
argued the cause for appellee. With her on the brief were
Jeffrey H. Wood, Acting Assistant Attorney General, Eric
Grant, Deputy Assistant Attorney General, and Jennifer
Scheller Neumann and John Smeltzer, Attorneys. Elizabeth
Trosman and James A. Ewing, Assistant U.S. Attorneys,
entered appearances.

    Before: TATEL, SRINIVASAN, and PILLARD, Circuit Judges.
                               2
    Opinion for the Court filed by Circuit Judge SRINIVASAN.

     SRINIVASAN, Circuit Judge: James Powers pleaded guilty
to one count of failing to remove asbestos-containing material
prior to renovation, in violation of 42 U.S.C. § 7413(c)(1). On
appeal, Powers raises procedural and substantive challenges to
the sentence imposed by the district court. He also contends
that he received ineffective assistance of counsel at sentencing.

     We do not reach the merits of Powers’s claims. With
regard to his procedural and substantive challenges to his
sentence, he waived his ability to appeal on those grounds as
part of his plea agreement. With regard to his claim of
ineffective assistance of counsel, he forfeited the claim for
purposes of this appeal by failing to assert it until his reply
brief. We therefore affirm the judgment of the district court.

                               I.

     For several months, Powers led efforts to convert a historic
property in Southeast Washington, D.C. into condominiums.
During construction, an environmental consultant visited the
renovation site and informed Powers that the building’s pipe
insulation, floor tiles, and wall board contained asbestos.
Under the Clean Air Act and regulations promulgated
thereunder, the asbestos needed to be removed before the
renovation could proceed. See 42 U.S.C. § 7412(b)(1); 40
C.F.R. § 61.145.

    Although Powers assured D.C. officials that he would halt
construction and abate the asbestos, he instead directed the
construction workers to continue the project. The workers
removed asbestos-containing materials without wearing
adequate protective gear. Also, instead of disposing of the
asbestos material in a safe place as required by law, the workers
                               3
left the material on the ground and in open dumpsters outside
the property.

     Once the D.C. Department of the Environment realized
that Powers had continued renovations without abating the
asbestos, the Department issued a cease and desist order. A
grand jury then indicted Powers for violating the Clean Air Act
and committing wire fraud.

     Powers pleaded guilty to one count of failing to remove
asbestos-containing material from the property before
renovating it, in violation of 42 U.S.C. § 7413(c)(1). As part
of the plea agreement, the parties agreed to a base offense level
of eight under the United States Sentencing Guidelines, and up
to a three-level reduction for Powers’s acceptance of
responsibility. The parties reserved their ability to present
argument to the district court on the applicability of two
sentencing enhancements: one for an ongoing discharge of a
hazardous substance, U.S.S.G. § 2Q1.2(b)(1)(A); the other for
an offense resulting in a substantial likelihood of death or
serious bodily injury, U.S.S.G. § 2Q1.2(b)(2). Powers agreed
that, if the enhancements applied, his estimated Sentencing
Guidelines range would be thirty-three to forty-one months and
a sentence within that range would be reasonable. He also
agreed to waive his right to appeal any sentence within or
below the Guidelines range, unless he claimed he received
ineffective assistance of counsel.

    At sentencing, Powers urged the district court to refrain
from applying the two sentencing enhancements, to vary
downward from the Guidelines range, and to impose a sentence
only of probation. The court found that the two enhancements
applied, but concluded that the resulting sentencing range of
twenty-four to thirty months was greater than warranted. The
court therefore sentenced Powers to twenty months of
                               4
imprisonment, to be followed by thirty-six months of
supervised release. Powers then brought this appeal.

                               II.

                               A.

     Powers seeks to raise both procedural and substantive
challenges to his sentence on appeal. The government argues
that we should not reach the merits of Powers’s arguments.
According to the government, Powers, as part of his plea
agreement, waived the right to appeal his sentence on the
grounds he now seeks to assert. We agree with the government.

     A criminal defendant may waive the right to appeal a
sentence, even before knowing what the sentence will be, if the
waiver is “knowing, intelligent, and voluntary.” United States
v. Guillen, 561 F.3d 527, 529-30 (D.C. Cir. 2009). To ensure
that a defendant’s waiver meets that standard, the district court
must conduct a colloquy with the defendant to review the terms
of the plea agreement, including any waiver of the right to
appeal. See Fed. R. Crim. P. 11(b)(1). On review, if the record
shows that a properly informed defendant made the decision
“with eyes open,” we will enforce an anticipatory waiver of the
right to appeal. Guillen, 561 F.3d at 529-30 (quoting United
States v. Cunningham, 145 F.3d 1385, 1391 (D.C. Cir. 1998)).

    Here, Powers validly waived his right to appeal his
sentence on the grounds that the sentence is procedurally or
substantively unreasonable. As part of his written plea
agreement, Powers expressly “waive[d] the right to appeal the
sentence in this case, including any term of imprisonment,”
unless he were to receive a sentence exceeding the statutory
maximum or the Guidelines range determined by the court, or
were to raise a claim that he received ineffective assistance of
counsel. App. 40.
                               5
     At the plea hearing, the district court reviewed the terms
of the plea agreement with Powers. The court explained that
Powers was relinquishing his “right to appeal except in the
limited exceptions” enumerated in the plea agreement. App.
129-30. When the court asked whether Powers understood
what he was giving up, he said he did. The court next observed
that the parties, having reserved their ability to present
arguments on the applicability of two sentencing
enhancements, left that determination to the court. The parties
acknowledged, however, that those reservations did not include
appeal rights. As a result, the court explained to Powers, even
if the court were to apply both of the disputed enhancements,
Powers could appeal only if the sentence exceeded the
Guidelines range. Powers again said he understood. After
Powers confirmed that he had no further questions about the
plea agreement, the court accepted his guilty plea, finding that
he had made his decision knowingly and voluntarily.

     Powers now seeks to challenge his sentence on appeal. He
argues that the district court erred in applying the two
sentencing enhancements and failed to consider the need to
avoid unwarranted sentencing disparities. He further contends
that his twenty-month sentence is substantively unreasonable
because it exceeds the sentences received by other defendants
in comparable situations. Because Powers waived his right to
appeal on those grounds in his written plea agreement, and
because the record shows that his waiver was knowing and
voluntary, Powers cannot bring those claims on appeal.

     In his reply brief, Powers advances three reasons for
denying enforcement of his appeal waiver. The government
initially asserts that Powers forfeited those challenges to the
waiver’s enforceability by raising them for the first time in his
reply brief. We disagree. It is true that appellants ordinarily
must raise any issues ripe for our consideration in their opening
                                6
briefs. See, e.g., Abdullah v. Obama, 753 F.3d 193, 199 (D.C.
Cir. 2014). But an appellant generally may, in a reply brief,
“respond to arguments raised for the first time in the appellee’s
brief.” 16AA Charles Alan Wright et al., Federal Practice and
Procedure: Jurisdiction § 3974.3 (4th ed. 2017); see MBI Grp.,
Inc. v. Credit Foncier Du Cameroun, 616 F.3d 568, 575 (D.C.
Cir. 2010).

     Consequently, Powers was not required to assume in his
opening brief that the government would rely on the appeal
waiver. Rather, he could wait to see if the government would
invoke the appeal waiver in its brief, and then, if so, contest the
appeal waiver’s enforceability in his reply brief. See United
States v. Goodson, 544 F.3d 529, 536 (3d Cir. 2008). But see
United States v. Arroyo-Blas, 783 F.3d 361, 367 (1st Cir.
2015). Powers therefore did not forfeit his challenges to the
appeal waiver’s enforceability by waiting to assert them until
his reply brief.

     On the merits, however, Powers’s arguments against
enforcing the appeal waiver are unpersuasive. Powers first
contends that his plea agreement is an unenforceable contract
of adhesion. He notes that, although the plea agreement limited
his appeal rights, the government remained free to appeal or
use his plea in future litigation. He also points to a provision
permitting the government to argue against a reduction for
acceptance of responsibility if he obstructed justice before
sentencing. As a result, Powers asserts, the plea agreement is
too one-sided to be enforceable. As support, he cites two
district court decisions concluding that a waiver of a right to
appeal a yet-to-be-imposed sentence is unenforceable. See
United States v. Raynor, 989 F. Supp. 43 (D.D.C. 1997);
United States v. Johnson, 992 F. Supp. 437 (D.D.C. 1997).
                                7
     Our decision in Guillen, however, later rejected that very
claim. An appeal waiver, we explained, gives the defendant
“an additional bargaining chip” to use in securing a plea
agreement with the government. Guillen, 561 F.3d at 530. We
therefore enforce a bargained-for appeal waiver unless the
defendant enters into it unknowingly, unintelligently, or
involuntarily. Here, Powers’s arguments about the fairness of
his plea agreement’s particular terms do not afford a basis for
questioning his knowing and voluntary consent to the
agreement, including the appeal waiver.

     Powers next argues that he could not have “intelligently”
agreed to the plea agreement because several of the
agreement’s terms are too complicated for a defendant to
comprehend. Specifically, he points to the ostensible difficulty
of distinguishing between his waiver of his rights to appeal or
collaterally attack his sentence, on one hand, and the parties’
reservation of their rights of allocution in connection with any
post-sentence motion, on the other hand. None of Powers’s
contentions on appeal about the complexity of the plea
agreement can carry the day in light of his repeated
affirmations to the district court that he understood the
agreement’s terms. Indeed, even now, Powers makes no
representation that he in fact misunderstood the agreement.

     Finally, Powers points to an alleged misstatement by the
district court concerning the government’s appeal rights. In the
pertinent colloquy, the court correctly explained that the parties
had left it to the court to determine whether to apply two
sentencing enhancements, but had agreed that, regardless of the
court’s decision, Powers would be barred from appealing on
the issue. The court also stated that the government could not
appeal if the court declined to apply the enhancements.
According to Powers, that statement was incorrect because the
                                 8
government would have been precluded only from backing out
of the agreement, not from appealing.

     Even assuming the court’s statement was incorrect in that
regard, Powers does not explain how the court’s misstatement
about the government’s appeal rights could have affected his
understanding of his own appeal rights. With regard to the
latter, the court spoke clearly and correctly: “if I rule that the
government is right [that the enhancements apply] and the
guidelines you’re facing are longer, you understand that you’re
not going to appeal that decision.” App. 130. Powers
confirmed he understood.

     In short, Powers gives us no reason to doubt that his waiver
of his right to appeal his sentence was knowing, intelligent, and
voluntary. We therefore decline to consider his procedural and
substantive challenges to his sentence.

                                B.

     Powers also seeks to raise one claim that falls outside the
scope of his appeal waiver. He argues, for the first time in his
reply brief, that his counsel rendered constitutionally
ineffective assistance by failing to marshal additional
mitigation evidence supporting a shorter sentence. The parties
agree that the appeal waiver, by its terms, does not encompass
claims of ineffective assistance of counsel. Powers, however,
forfeited his ineffective-assistance-of-counsel claim for
purposes of this appeal by failing to raise it in his opening brief.

     As we have explained, a defendant generally may raise
challenges to the enforceability of an appeal waiver for the first
time in a reply brief, in response to the government’s
invocation of the waiver. Powers’s ineffective-assistance-of-
counsel claim, though, does not pertain to the enforceability of
his appeal waiver. Powers does not contend, for instance, that
                                 9
his counsel rendered ineffective assistance in advising Powers
about the decision to enter into the plea agreement or to waive
his right to appeal. See Guillen, 561 F.3d at 530-31.

     Instead, Powers asserts a freestanding ineffective-
assistance-of-counsel claim, untethered to the enforceability of
his appeal waiver. He contends that his counsel rendered
constitutionally ineffective assistance in connection with his
sentencing. Because that argument does not go to the appeal
waiver’s enforceability, it is subject to the ordinary rule
requiring an appellant to raise arguments in an opening brief.
See Abdullah, 753 F.3d at 199. And Powers, by waiting to
present the claim until his reply brief, forfeited it for purposes
of this appeal. We note, though, that his forfeiture of the
ineffective-assistance-of-counsel claim on direct appeal does
not affect his ability to assert it on collateral review in a motion
under 28 U.S.C. § 2255. Cf. Massaro v. United States, 538
U.S. 500, 504 (2003).

                       *    *    *    *   *

     For the foregoing reasons, we affirm the judgment of the
district court.

                                                       So ordered.
