In re: Contempt Proceedings Against Carpenter

Appellate Case: 26-6073 Document: 54-1 Date Filed: 08/18/2026 Page: 1 FILED United States Court of Appeals UNITED STATES COURT OF APPEALS Tenth Circuit FOR THE TENTH CIRCUIT August 18, 2026 _________________________________ Christopher M. Wolpert Clerk of Court In re: Contempt Proceedings Against DANIEL E. CARPENTER. ------------------------------ UNITED STATES OF AMERICA, Plaintiff - Appellee, v. No. 26-6073 (D.C. Nos. 5:24-MC-00005-HE & DANIEL E. CARPENTER, 5:14-FJ-00005-HE) (W.D. Okla.) Defendant - Appellant. _________________________________ 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 Appellate Case: 26-6073 Document: 54-1 Date Filed: 08/18/2026 Page: 2 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 Appellate Case: 26-6073 Document: 54-1 Date Filed: 08/18/2026 Page: 3 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 Appellate Case: 26-6073 Document: 54-1 Date Filed: 08/18/2026 Page: 4 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.

Appellate Case: 26-6073 Document: 54-1 Date Filed: 08/18/2026 Page: 5

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 Appellate Case: 26-6073 Document: 54-1 Date Filed: 08/18/2026 Page: 6 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