Henry Drake Shirley, Appellant-Defendant v. State of Indiana, Appellee-Plaintiff (2026)

MEMORANDUM DECISION

Case Summary

[1] Pursuant to a plea agreement, Henry Shirley pled guilty to a felony, a misdemeanor, and a habitual offender enhancement. The plea agreement provided that Shirley would be sentenced to 1,095 days on the habitual offender enhancement, with placement decided by the trial court. Shirley also agreed to waive his right to appeal his sentence. After the court ordered Shirley to serve the 1,095-day sentence enhancement in the Department of Correction (DOC), it told him that it would allow him to appeal that placement decision. Shirley then filed this appeal, which the State moved to dismiss on the grounds that it was barred by the plea agreement's appeal waiver. Because we agree with the State, we dismiss Shirley's appeal.

Facts and Procedural History

[2] The State charged Shirley with Level 6 felony resisting law enforcement, Class B misdemeanor leaving the scene of an accident, Class C misdemeanor reckless driving, and two traffic infractions. It also sought a habitual offender sentence enhancement.¹ Shirley, assisted by counsel, entered into a plea agreement with the State in which he agreed to plead guilty to Level 6 felony resisting law enforcement with the habitual offender enhancement and Class B misdemeanor leaving the scene of an accident. In exchange, the State agreed to dismiss the remaining counts.

[3] The plea agreement provided that Shirley would be sentenced to 365 days on work release for the felony conviction and 180 days on work release for the misdemeanor, served concurrently. The felony sentence was to be enhanced by 1,095 days for the habitual offender enhancement, “with placement open to the Court ․” Appellant's Appendix Vol. 2 at 66. As a condition of the plea agreement, Shirley “knowingly and voluntarily agree[d] to waive the right to appeal the sentence on the basis that it is erroneous or for any other reason so long as the [court] sentence[d] him[ ] within the terms of th[e] agreement.” Id. He also waived his rights “to challenge the trial court's finding and balancing of mitigating and aggravating factors” and to “have the Court of Appeals review his sentence under Indiana Appellate Rule 7(B).” Id.

[4] At a combined guilty plea and sentencing hearing, the trial court confirmed that Shirley understood that he was “giving up the right to appeal the conviction and sentence” under the plea agreement. Transcript at 9. The court also noted that the plea agreement entitled it to determine placement on the habitual offender enhancement, which meant the sentence “could be the DOC ․” Id. at 13. The trial court ultimately accepted Shirley's plea, sentenced him in accordance with the plea agreement's requirements, and then heard argument with respect to placement for the 1095-day enhancement. The parties disputed whether the court was authorized by statute to order Shirley to serve the enhancement on work release. After the court determined that it could not suspend Shirley's sentence on the enhancement, it ordered him to serve those 1,095 days in the DOC. Despite the appeal waiver in the plea agreement, the court appointed appellate counsel for Shirley and stated that “since placement was open to [the court], ․ and I've had to interpret statutes[,] ․ I think it's only fair that he have an opportunity to appeal this.” Id. at 36.

[5] Shirley appealed, and after he filed his brief, the State filed a motion to dismiss. It asserted Shirley had waived his right to appeal in the plea agreement. After Shirley responded, the motions panel issued an order holding the State's motion in abeyance to be addressed in this opinion. The State then filed a brief reiterating its waiver arguments, to which Shirley did not reply.

Discussion and Decision

[6] Shirley argues that the trial court erred in determining that it did not have statutory authority to permit him to serve his habitual offender enhancement on work release. But we need not address this question because the State's argument that Shirley waived his right to appeal his sentence is dispositive.

[7] This case is on all fours with the Supreme Court's recent decision in Anderson v. State, 269 N.E.3d 817 (Ind. 2025). There, Anderson entered into a plea agreement whereby the State agreed she would serve a maximum executed sentence of four years, but the total term was left to the trial court's discretion. Id. at 819. The plea agreement contained the following appeal waiver:

Defendant hereby waives the right to appeal any sentence imposed by the Court, including the right to seek appellate review of the sentence pursuant to Indiana Appellate Rule 7(B), so long as the Court sentences the defendant within the terms of this plea agreement.

Id. At a combined plea and sentencing hearing, the trial court accepted Anderson's guilty plea and then heard evidence and argument on sentencing, including potential aggravating and mitigating circumstances. Id. The court sentenced Anderson to three years executed in the DOC and three years suspended to probation. Id. at 819-20. “After the hearing, the trial court, unprompted, told Anderson she had ‘a right to appeal the sentence imposed in this case, not the conviction, but you do have a right to appeal the sentence.’ ” Id. at 820.

[8] Anderson appealed, arguing the trial court abused its sentencing discretion. As for her appeal waiver, she contended it was limited in scope as evidenced by the court's misstatement from the bench. Id. The State moved to dismiss Anderson's appeal on grounds that her arguments were subject to the appeal waiver, and a divided appellate motions panel agreed. Id. The Supreme Court granted transfer but similarly dismissed the appeal.

[9] In its opinion dismissing Anderson's appeal, the Supreme Court noted Indiana precedent has “consistently recognized the enforceability of appeal waivers based on the contract principles underlying them.” Id. at 821. However, it observed that “even a comprehensive waiver that purports to foreclose all appeals cannot legally prevent a defendant from challenging an unbargained-for ‘illegal’ sentence.” Id. at 818. As such, Anderson squarely addressed “what qualifies as an illegal sentence.” Id. at 819. The Court ultimately held “that a sentence is ‘illegal’ only if it is outside the prescribed statutory range or is unconstitutional.” Id. at 822. This holding resolved a split within Court of Appeals jurisprudence and brought Indiana's precedent into alignment with the Legislature's overall sentencing scheme. Id. (citing Ind. Code § 35-38-1-7.1(d) (“A court may impose any sentence that is: (1) authorized by statute; and (2) permissible under the Constitution of the State of Indiana; regardless of the presence or absence of aggravating circumstances or mitigating circumstances.”)). The Court further reasoned that its holding advanced “an important principle associated with plea agreements, which is that both parties receive something of value by negotiating them.” Id. at 823. Anderson benefited by limiting her number of convictions and capping her time in the DOC, and she had agreed to benefit the State by saving it the expense of going to trial and defending against an appeal. Id.

[10] Regarding Anderson's specific claims, the Court found that “an alleged defect in the trial court's sentencing discretion, including determining and applying aggravating and mitigating factors, does not amount to an unconstitutional, illegal sentence.” Id. Because Anderson agreed to a “clear and comprehensive” open plea which only prohibited the court from ordering her to serve more than four years in the DOC, the Court easily found that Anderson's sentence fell within the terms of the plea agreement and the appeal waiver prohibited her appeal. Id. at 824. Importantly, the Court also rejected Anderson's argument that the trial court's misstatement that she could appeal was evidence “of the appeal waiver's ‘limited scope.’ ” Id. On this point, the Court reasoned that “Indiana follows ‘the four corners rule’ that ‘extrinsic evidence is not admissible to add to, vary or explain the terms of a written instrument if the terms of the instrument are susceptible of a clear and unambiguous construction.’ ” Id. (quoting Univ. of S. Ind. Found. v. Baker, 843 N.E.2d 528, 532 (Ind. 2006)). Because the plea agreement's appeal waiver was “unambiguous[,]” the Court found “the trial court's misstatement about Andersons’ appellate rights d[id] not alter or affect” its broad scope. Id.

[11] Anderson requires this appeal be dismissed. Here, Shirley argues that the trial court misinterpreted various statutes and therefore failed to understand that it “had discretion to determine whether [Shirley] should be committed to the [DOC], or whether an alternative Community Corrections placement was appropriate.” Appellant's Br. at 11. But we need not address that question because Shirley “waive[d] the right to appeal the sentence on the basis that it is erroneous or for any other reason so long as the [court] sentence[d] him[ ] within the terms of th[e] agreement.” Appellant's App. Vol. 2 at 66. Because the appeal waiver was clear and unambiguous, placement in the DOC was contemplated by the plea agreement, and Shirley does not raise an issue outside the scope of the waiver or argue that his sentence was illegal as defined in Anderson, his appeal must be dismissed. And while we recognize the court's attempt to restore Shirley's right to appeal was not a mere misstatement like that in Anderson, the court had no authority—regardless of whether it had interpreted statutes and believed Shirley should have the right to appeal—to strike the appeal waiver from the plea agreement. See Davis v. State, 217 N.E.3d 1229, 1234 (Ind. 2023) (“While trial judges have discretion to accept or reject plea agreements, courts are not empowered to change any of the terms.”), as modified on reh'g.

[12] Finally, we flag for the parties and the trial court that in a unanimous opinion respecting the denial of transfer in Pratcher v. State, our Chief Justice provided guidance to courts and attorneys to help combat the persistent issue of defendants receiving “incorrect advisements from our trial courts about appeal waivers.” 273 N.E.3d 824, 824-25 (Ind. Feb. 11, 2026) (mem.). Her recommendations were intended “to ensure defendants are not misled and to protect the finality of plea agreements.” Id. at 824. The Chief Justice outlined the best practice as follows:

When a defendant signs a plea agreement that leaves sentencing discretion to the trial court and contains a waiver of the right to appeal the sentence, the court should:

1. Explain that the defendant would ordinarily have the right to appeal their sentence, but the plea agreement contains a waiver limiting that right.

2. Read the appeal-waiver provision to the defendant.

3. Explain that the provision waives the defendant's right to appeal the sentence to be imposed, except for:

• any issue that falls outside the scope of the waiver;

• a sentence that violates the plea agreement; or

• a sentence that is illegal because it falls outside the prescribed statutory range or is unconstitutional.

4. Confirm the defendant understands the consequences of the appeal-waiver provision before accepting the guilty plea.

Attorneys also have a role in ensuring appeal-waiver provisions are clear and defendants are accurately advised. Given the stakes in preserving finality and certainty, the State should draft appeal-waiver provisions that unambiguously and specifically describe which appeal rights the defendant is waiving and retaining. Defense counsel should then confirm that the provisions are clear and that their clients understand these rights. And counsel for both sides should respectfully intervene during a guilty plea hearing to correct any confusing or incorrect statements by a judge. Together, the bench and bar can ensure that defendants are properly advised so that plea agreements achieve their intended finality.

Id. at 825.

Conclusion

[13] For the foregoing reasons, we dismiss Shirley's appeal.

FOOTNOTES

1.   Ind. Code § 35-50-2-8(d).

DeBoer, Judge.

Brown, J., and Altice, J., concur.