In re: Contempt Proceedings Against Carpenter

UNITED STATES COURT OF APPEALS

FOR THE TENTH CIRCUIT
_________________________________
In re: Contempt Proceedings Against
DANIEL E. CARPENTER.

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UNITED STATES OF AMERICA,

Plaintiff - Appellee,

v.

DANIEL E. CARPENTER,

Defendant - Appellant.

No. 26-6073
(D.C. Nos. 5:24-MC-00005-HE &
5:14-FJ-00005-HE)
(W.D. Okla.)
_________________________________
ORDER AND JUDGMENT
*

_________________________________
Before EID, KELLY, and FEDERICO, Circuit Judges.
_________________________________
Pursuant to a plea agreement, Daniel E. Carpenter pleaded guilty to criminal
contempt and was sentenced to no prison time, five years of supervised release, and a
$100,000 fine. He filed an appeal, but his plea agreement contained an appeal waiver
that the government moved to enforce under United States v. Hahn, 359 F.3d 1315,
1328 (10th Cir. 2004) (en banc) (per curiam). We granted the government’s motion

*
This order and judgment is not binding precedent, except under the doctrines
of law of the case, res judicata, and collateral estoppel. It may be cited, however, for
its persuasive value consistent with Fed. R. App. P. 32.1 and 10th Cir. R. 32.1.
FILED
United States Court of Appeals
Tenth Circuit

August 18, 2026

Christopher M. Wolpert
Clerk of Court
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and dismissed the appeal. In re Carpenter, Nos. 25-6198, 26-6003, 2026 WL
852232, at *4 (10th Cir. Mar. 27, 2026).
During the pendency of his appeal, Mr. Carpenter filed several motions in the
district court requesting dismissal of the case. The district court denied those
motions on April 29, 2026. Mr. Carpenter appeals from the district court’s post-
judgment rulings,
1
and the government has again moved to enforce the appeal waiver.
We grant the government’s motion and dismiss this appeal.
I. Background
In February 2025, Mr. Carpenter entered into a plea agreement in which he
pleaded guilty to criminal contempt for violating an order prohibiting him from
interfering with certain assets involved in an underlying civil matter. The agreement
stated that he “knowingly and voluntarily” waived his right to appeal his guilty plea.
Mot. to Enforce, Attach. 1 at 8. He also waived the right to appeal “any other aspect
of [his] conviction,” including his “sentence . . . any fines or restitution, and the
manner in which the sentence is determined,” provided his sentence required no
prison time. Id. at 8–9. In return, the government agreed, among other things, that it

1
Because Mr. Carpenter appears pro se, we construe his pleadings liberally.
Garrett v. Selby Connor Maddux & Janer, 425 F.3d 836, 840 (10th Cir. 2005).
However, we “will not allow liberal pleading rules and pro se practice to be a vehicle
for abusive documents. Our pro se practice is a shield against the technical
requirements of a past age; it is not a sword with which to insult a trial judge.” Id. at
841 (internal quotation marks omitted). We admonish Mr. Carpenter to avoid
abusive language in any future pro se pleadings.
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would waive its right to appeal if Mr. Carpenter’s sentence included a fine but no
incarceration.
At the change-of-plea hearing, Mr. Carpenter assured the district court that he
understood the plea agreement, that he had discussed its terms with his counsel, and
that he understood the rights he was waiving in the plea agreement. He also
represented to the court that his guilty plea and waiver of rights were made
voluntarily and not as a result of any pressure or threats. The district court accepted
the guilty plea and found that it was made knowingly and voluntarily.
In November 2025, the district court sentenced Mr. Carpenter to no prison
time, five years of supervised release, and a $100,000 fine. Mr. Carpenter appealed.
In response to the government’s motion to enforce the appeal waiver, Mr. Carpenter
made four principal arguments: that the plea waiver should not be enforced because
the government breached the plea agreement; that the district court in the underlying
civil lawsuit lacked jurisdiction; that he did not knowingly and voluntarily agree to a
sentence that included a $100,000 fine and five years of supervised release; and that
enforcing the waiver would result in a miscarriage of justice because supervised
release may not be imposed in the absence of a prison sentence and the waiver was
otherwise unlawful. This court rejected those arguments, granted the government’s
motion, and dismissed the appeal. See In re Carpenter, 2026 WL 852232, at *4.
Before this court granted the government’s motion to enforce the appeal
waiver, Mr. Carpenter filed several lengthy motions in district court. His motions
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requested the court to approve hybrid representation and to dismiss the case and
vacate the sentence. In denying the motions, the district court observed:
The issues raised in [the motions] are not new. Mr. Carpenter has raised
the same issues on multiple occasions. [He] does not get to file a new
motion every time a ruling is made he disagrees with. This Court and
the Tenth Circuit Court of Appeals have already addressed these issues,
and [the motions] are denied.

R. vol. III at 344. This appeal followed.
II. Discussion
Mr. Carpenter makes several arguments in support of his claim that the appeal
waiver is unenforceable, but we have already rejected almost all of them in his previous
appeals. First, he argues his conviction is invalid because the district court in the
underlying civil lawsuit lacked jurisdiction, but we previously rejected that argument
because “the district court’s authority to hold Carpenter in criminal contempt is separate
from its jurisdiction over the underlying civil matter.” In re Carpenter, 2026 WL
852232, at *1. Second, he argues his plea and waiver of rights were not knowing and
voluntary, but we have already rejected the proposition that a defendant’s waiver is valid
only if he knows with specificity the results he forfeits. Id. at *2. Third, Mr. Carpenter
argues his sentence is illegal because supervised release can be imposed only after a
period of incarceration. We rejected that argument as well. Id. at *3. Finally, he argues
that the government breached the plea agreement. We previously rejected that argument
because he failed to point to any actions by the government. Id. at *1.
Because we have already resolved these arguments in a prior appeal,
Mr. Carpenter is barred from raising them again under the law-of-the-case doctrine.
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See Entek GRB, LLC v. Stull Ranches, LLC, 840 F.3d 1239, 1240 (10th Cir. 2016) (“Law
of the case doctrine permits a court to decline the invitation to reconsider issues already
resolved earlier in the life of the litigation.”). As we explained in Entek:
Without [the law-of-the-case doctrine] an adverse judicial decision would
become little more than an invitation to take a mulligan, encouraging
lawyers and litigants alike to believe that if at first you don’t succeed, just
try again. A system like that would reduce the incentive for parties to put
their best effort into their initial submissions on an issue, waste judicial
resources, and introduce even more delay into the resolution of lawsuits
that today often already take long enough to resolve. All of which would
gradually undermine public confidence in the judiciary.

Id. (brackets, ellipsis, and internal quotation marks omitted).
Mr. Carpenter now asserts that the government breached the plea agreement by
requesting a period of supervised release. But the law-of-the-case doctrine extends
“to additional supplemental arguments on those same issues that the litigant could
have but failed to present the first time around.” Id. at 1242. And in any event, the
plea agreement contains an integration clause stating that it contains the entire
agreement between the government and Mr. Carpenter—and it contains no
representation by the government that it would not request supervised release.
The decision whether to apply the law-of-the-case doctrine is a matter of
judicial discretion, and “we may entertain relitigation of settled issues when the
failure to do so would work a manifest injustice.” Id. at 1242 (internal quotation
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marks omitted). Nothing in Mr. Carpenter’s briefing convinces us that application of
the doctrine in this case would work such an injustice.
2

This is Mr. Carpenter’s sixth appeal in this criminal contempt case, three of
which he filed after his sentencing. As detailed above, the present appeal rehashes
arguments previously presented by Mr. Carpenter and ruled upon by this court. We
therefore warn Mr. Carpenter that he may be subject to sanctions, including the
possible imposition of filing restrictions, if he again files an appeal challenging his
criminal contempt conviction or sentence with arguments substantially similar to
those presented here or in Appeal Numbers 25-6198 and 26-6003.
III. Conclusion
We grant the government’s motion to enforce the appeal waiver and dismiss
this appeal. We deny Mr. Carpenter’s motion to vacate the district court’s June 9,
2026 order in the underlying civil ligation or in the alternative for stay. We also
deny Mr. Carpenter’s motion for leave to file a sur-reply.
Entered for the Court

Per Curiam

2
Relatedly, Mr. Carpenter argues that enforcement of the appeal waiver would
result in a miscarriage of justice based on the Supreme Court’s recent decision in
Hunter v. United States, 146 S. Ct. 1702 (2026). In Hunter, the Court “approve[d]
the majority view among the courts of appeals that an appeal waiver is unenforceable
when it would result in a miscarriage of justice.” Id. at 1713. The Tenth Circuit has
long held that majority view. See Hahn, 359 F.3d at 1325. And Mr. Carpenter has
identified nothing in Hunter suggesting that enforcement of the appeal waiver would
work a miscarriage of justice in this case.
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