In re Jeffrey R. Gay II

NOTICE: This opinion is subject to motions for reargument under V.R.A.P. 40 as well as formal
revision before publication in the Vermont Reports. Readers are requested to notify the Reporter
of Decisions by email at: JUD.Reporter@vermont.gov or by mail at: Vermont Supreme Court, 109
State Street, Montpelier, Vermont 05609-0801, of any errors in order that corrections may be made
before this opinion goes to press.

2019 VT 67

No. 2018-323

In re Jeffrey R. Gay II Supreme Court

On Appeal from
Superior Court, Chittenden Unit,
Civil Division

May Term, 2019

Robert A. Mello, J.

Matthew Valerio, Defender General, and Jill P. Martin and Seth Lipschutz, Prisoners’ Rights
Office, Montpelier, for Petitioner-Appellant.

David Tartter, Deputy State’s Attorney, Montpelier, for Respondent-Appellee.

PRESENT: Reiber, C.J., Skoglund, Robinson, Eaton and Carroll, JJ.

¶ 1. CARROLL, J. Defendant appeals orders denying his motion for summary

judgment and granting summary judgment in favor of the State on his petition for post-conviction

relief (PCR). He argues that the superior court erred when it concluded that, by pleading guilty to

a charge carrying a habitual-offender enhancement, he waived the right to subsequently contest

the sufficiency of the pleas in the underlying convictions that made him subject to the

enhancement. We affirm.

¶ 2. In 2014, defendant pled no contest to obstruction of justice. As part of his plea

colloquy with the sentencing court, defendant acknowledged that by changing his plea from not

guilty to no contest, he was giving up his right to appeal, which he would have had if he had
maintained his not-guilty plea, gone to trial, and been convicted. The court imposed a sentence

that was enhanced under Vermont’s habitual-offender statute, 13 V.S.A. § 11.1 Between 2001 and

2006, defendant was convicted of four felonies that enhanced the sentence on the obstruction-of-

justice conviction. He pled guilty to two of those convictions—false pretenses and grand

larceny—at one proceeding in 2004.

¶ 3. In 2018, defendant filed a PCR petition, seeking to vacate the sentence imposed on

the 2014 obstruction-of-justice conviction. He argued that he was entitled to a resentencing

because his pleas to the charges of false pretenses and grand larceny in 2004 were not made

knowingly and voluntarily. Specifically, he alleged that the pleas were deficient because the court

failed to elicit from him an admission to the factual basis supporting each of the charges.

Defendant argued that without these two prior convictions, his sentence on the obstruction-of-

justice conviction should not have been enhanced pursuant to 13 V.S.A. § 11.

¶ 4. Defendant filed a motion for summary judgment. His motion relied, in part, on the

transcript of the colloquy he and the court engaged in during the 2004 change-of-plea hearing on

the false-pretenses and grand-larceny charges. He argued that the colloquy did not satisfy the

dictates of In re Stocks, 2014 VT 27, ¶¶ 17, 20. 196 Vt. 160, 94 A.3d 1143 (vacating convictions

and determining that plea was not voluntary based on court’s failure to elicit admission to facts

forming basis for charges, as required by Vermont Rule of Criminal Procedure 11(f)). Defendant

urged the court to vacate his 2014 sentence and to impose a sentence no greater than five years to

serve.

1
The maximum sentence defendant would have faced for obstruction of justice, without a
habitual-offender enhancement, was five years. 13 V.S.A. § 3015. As a habitual offender, he was
subject to a sentence of up to life imprisonment upon conviction of a felony after having been
previously convicted of three felonies. Here, under the plea agreement, defendant was sentenced
to zero-to-thirty years to serve.
2
 ¶ 5. The State opposed defendant’s motion for summary judgment and cross-moved for

summary judgment. The State argued that it was immaterial whether the colloquy resulting in the

2004 convictions satisfied Rule 11(f) because defendant, by entering a knowing and voluntary plea

to obstruction of justice, waived any challenge to the sufficiency of the plea colloquy on the

underlying convictions used to enhance his sentence. Because he entered a knowing and voluntary

guilty plea to the obstruction-of-justice charge, and the agreed-upon sentence was imposed,

defendant was barred from collaterally attacking the validity of the 2004 convictions and had

waived all nonjurisdictional defects in that proceeding.

¶ 6. The court denied defendant’s motion for summary judgment and granted the State’s

cross-motion for summary judgment. It reviewed the transcript of the 2004 proceeding and

ultimately concluded that the change-of-plea colloquy on the false-pretenses and grand-larceny

charges suffered from the same deficiencies this Court identified in Stocks.2 Defendant did not

argue that his plea to the obstruction-of-justice charge was not made knowingly and voluntarily.

The court then reviewed the transcript of that proceeding and found that it complied with Rule

11(f) and concluded that defendant made his plea knowingly and voluntarily. Finally, the court

relied, in part, on In re Torres, 2004 VT 66, ¶ 9, 177 Vt. 507, 861 A.2d 1055 (mem.), to hold that

defendant had waived all nonjurisdictional defects in the 2004 proceedings by entering a knowing

and voluntary plea to a charge of obstruction of justice and was barred from collaterally attacking

the convictions used to enhance his sentence. Defendant appealed.

¶ 7. We review the court’s summary-judgment decisions de novo, applying the same

standard as the trial court. Sabia v. Neville, 165 Vt. 515, 523, 687 A.2d 469, 474 (1996). Summary

2
Because we agree with the trial court that petitioner waived the right to collaterally attack
the 2004 convictions, we need not decide whether the changes of plea met the dictates of Rule
11(f) under Stocks.
3
judgment is appropriate when there are no genuine issues of material fact, and a party is entitled

to judgment as a matter of law. V.R.C.P. 56(a).

¶ 8. On appeal, defendant attempts to distinguish Torres, arguing that it is inapplicable

because, in that case, we addressed only the legality of a conviction that was enhanced by a prior

illegal conviction, but not the sentence that was imposed. He further submits that this case is

controlled by In re Manning, 2016 VT 53, 202 Vt. 111, 147 A.3d 645. In Manning, we reversed

the sentence imposed on a DUI-4 conviction after concluding that the plea colloquy on a prior

DUI-3, used to enhance the defendant’s sentence on the DUI-4, was inadequate. Id. ¶¶ 18-19.

Finally, defendant argues that, at best, these two cases are in conflict and therefore Manning

controls as the more recent case.

¶ 9. We conclude that Torres is applicable here. In Torres, the defendant filed a PCR

petition, claiming that his conviction for second-degree aggravated domestic assault required a

prior domestic-assault conviction and that, because he had no such prior conviction, his conviction

for second-degree aggravated domestic assault must be vacated.3 The defendant also claimed that

his attorney was ineffective when he failed to investigate the alleged prior conviction and allowed

him to plead guilty to the second-degree aggravated domestic assault charge. We acknowledged

that the defendant had not previously been convicted of domestic assault—the case had been

charged but was later dismissed—but held that the defendant waived his right to challenge his

supposed prior domestic-assault conviction as an element of his subsequent aggravated-domestic

conviction when he pled guilty to the subsequent offense.4 Torres, 2004 VT 66, ¶ 1.

3
A person may be charged with second-degree aggravated domestic assault when he or
she commits a domestic assault and has previously been convicted of domestic assault. 13
V.S.A. § 1044(a)(2)(B).
4
We remanded the claim of ineffective assistance of counsel based on the defendant’s
attorney’s allegedly deficient performance investigating the existence of the defendant’s prior
conviction in preparation for the plea hearing, and the attorney’s advice that the defendant plead
4
 ¶ 10. We reiterated that a voluntary plea of guilty, with an acknowledgement that by

pleading guilty the defendant is giving up appeal rights, waives all “non-jurisdictional defects” in

the prior proceedings, with limited exceptions that are “inherent in the requirement that pleas be

made knowingly and voluntarily.” Torres, 2004 VT 66, ¶ 9 (quotations omitted); see also State v.

Armstrong, 148 Vt. 344, 345-46, 533 A.2d 1183, 1184 (1987) (noting that guilty plea constitutes

waiver of “procedural shortcomings,” claims that “prosecution obtained evidence unlawfully,” and

“all nonjurisdictional defects in the proceedings leading up to the plea, including allegedly illegal

searches and seizures”). Thus, a guilty plea or plea of no contest waives most appellate challenges

to a defendant’s conviction, with few exceptions.5 See United States v. Calderon, 243 F.3d 587,

590 (2d Cir. 2001) (holding that venue is nonjurisdictional); United States v. Schuman, 127 F.3d

815, 818, n.* (9th Cir. 1997) (Kozinski, J., concurring) (listing jurisdictional issues, which are not

subject to waiver by guilty plea).

¶ 11. In Torres, after examining the record of the plea to the second-degree aggravated

assault, we determined that the defendant entered a knowing and voluntary guilty plea to the charge

and concluded that he “understood that he was giving up appeal rights by pleading [guilty].” 2004

VT 66, ¶ 11. Therefore, we concluded, “he may not challenge his conviction now on grounds that

he has never been convicted of a domestic assault, and thus cannot be guilty of committing a

‘second or subsequent offense’.” Id.

¶ 12. Torres dictates the outcome here. Indeed, it is undisputed that defendant pled no

contest to obstruction of justice, and, in doing so, knowingly, voluntarily, and expressly waived

guilty at that hearing, because the PCR court did not address it. Id. ¶¶ 1, 4, 15. In addition, in his
amended petition, the defendant also argued that his enhanced sentence should be vacated.
5
The waiver rule does not apply to conditional guilty pleas, which require the consent of
the State and approval of the court. V.R.Cr.P. 11(a)(2) (“[A] defendant may enter a conditional
plea of guilty or nolo contendere, reserving in writing the right, on appeal from the judgment, to
review the adverse determination of any specified pretrial motion. If the defendant prevails on
appeal, he shall be allowed to withdraw his plea.”).
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his right to appeal. This waived his right to appeal all nonjurisdictional defects to his obstruction

charge, and, under Torres, this includes the existence of any underlying convictions that made him

eligible for a sentencing enhancement.

¶ 13. Defendant’s argument that the waiver doctrine applies only to challenges to

convictions and not to sentences is unavailing. The defendant in Torres argued that both his

conviction and sentence should be vacated. Id. ¶ 4. He challenged the enhancement to the charge,

and thus also challenged the increase to his sentence, based upon the alleged prior conviction. In

Torres we were not required to address the sentence because we held that the defendant waived

the right to challenge the conviction upon which the sentence was based. Id. ¶ 15. Here, defendant

challenges a sentence that was enhanced by prior convictions. Any distinction between Torres and

this case with respect to what was challenged is of no moment. As in Torres, here defendant

attempts to collaterally attack nonjurisdictional defects in a prior proceeding. He expressly waived

this right when he entered a voluntary and knowing no contest plea to obstruction of justice, and,

in doing so, affirmed that he understood that he was relinquishing any right to appeal.

¶ 14. Defendant’s next argument is that Manning is controlling. However, the procedural

posture of this case is easily distinguished from that of Manning because Manning did not involve

a knowing and voluntary guilty plea that would subject the underlying offenses to waiver. In

Manning, the defendant was charged with driving under the influence, fourth offense, which

required proof of three prior DUI convictions. While the case was still pending, the defendant

filed a PCR petition seeking to vacate one of the prior convictions, a DUI third offense (DUI-3),

arguing that the plea colloquy in his prior case—the DUI-3—did not comply with Vermont Rule

of Criminal Procedure 11(d) and (f). 2016 VT 53, ¶ 2. The petition was held in abeyance until

the outcome of the DUI-4 proceeding was determined. Id. ¶ 3. The defendant was convicted in the

DUI-4 case and the court then addressed the PCR petition. Id. ¶¶ 3-4. The trial court held that the

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change-of-plea colloquy on the underlying DUI-3 charge satisfied Rule 11(d) and (f) and therefore

entered judgment for the State. Id. ¶¶ 8-10.

¶ 15. On appeal, the defendant argued that the DUI-3 conviction must be vacated because

the court erred in its determination that the plea colloquy for the DUI-3 conviction satisfied Rule

11. We reversed and remanded, holding that the guilty plea did not satisfy Rule 11 because the

plea colloquy on the DUI-3 conviction lacked any recitation of the elements of the offense and the

factual basis supporting the charge was not admitted to by the defendant. Id. ¶¶ 15, 18. However,

we rejected the defendant’s request that we vacate the DUI-3 conviction and held that the proper

remedy was to resentence the defendant on his DUI-4 conviction. Id. ¶ 19. We relied on our

decision in State v. Boskind, 174 Vt. 184, 189-92, 802 A.2d 358, 363-65 (2002), to reiterate that

when a defendant is in custody pursuant to an enhanced sentence, he is limited to challenging the

enhancement of that sentence and may not attack the conviction on which the enhancement is

based. Manning, 2016 VT 53, ¶ 20; see In re Collette, 2008 VT 136, ¶ 8, 185 Vt. 210, 969 A.2d

101 (holding that relief in such a case is limited to striking enhanced sentence rather than vacating

final, prior conviction).

¶ 16. The Manning holding is not in conflict with Torres and is not applicable to this

case. Manning is not a waiver case. There the defendant preserved his right to challenge his

enhanced sentence by filing a PCR petition attacking the legality of a previous conviction while

the enhanced charge was pending. He did not enter a guilty or no contest plea to the enhanced

charge and, thus, did not knowingly and voluntarily waive his right to appeal nonjurisdictional

defects. In Manning, we clarified that the proper remedy under the circumstances there was to

challenge the enhanced sentence. Defendant does that here, but this remedy is not available to him

7
after having entered a knowing and voluntary plea of no contest to the enhanced charge of

obstruction.6

¶ 17. The court did not err in concluding that the State was entitled to judgment as a

matter of law. Defendant waived his right to challenge the legality of his underlying convictions

and the imposition of an enhanced sentence when he entered a knowing and voluntary plea to

obstruction of justice.

Affirmed.

FOR THE COURT:

Associate Justice

¶ 18. ROBINSON, J., concurring. I concur in the majority opinion, but write

separately to highlight the practical tension I believe this decision creates in our case law.

¶ 19. I concur with the majority because on this record defendant clearly waived any

challenge to the prior convictions upon which the habitual offender enhancement was based. The

court expressly advised defendant that he was charged with obstruction of justice with a habitual

6
The other cases cited in defendant’s post-argument Vermont Rules of Appellate
Procedure 28(j) filing are either distinguishable or inapplicable. Class v. United States, 583 U.S.
__, __, 138 S. Ct. 798, 807 (2018), holds that a defendant’s guilty plea does not waive his right to
challenge the constitutionality of a federal statute under which he was convicted. This case
involved a written plea agreement that allowed the defendant to preserve certain appeal issues
while prohibiting him from raising others. The Court relied on the fact that the defendant’s right
to challenge the constitutionality of the statute was not listed in either category as permitted or
prohibited. Id. at __, 138 S. Ct. at 802, 805. It is noteworthy that the Court there also reiterated
that a valid guilty plea relinquishes any claim that would contradict the admissions necessarily
made upon entry of a voluntary plea of guilty. Id. at __, 138 S. Ct. at 804. That is precisely the
case here. In State v. Phillips, 2018 VT 85, ¶ 18, __ Vt. __, 195 A.3d 1099, we held that it was
permissible for the defendant to waive an ex-post-facto challenge to his charge upon the entry of
a knowing and voluntary plea. It is difficult to discern how Phillips lends support to defendant’s
arguments here and we will not strain to do so. Finally, defendant cites to State v. Hance, 157 Vt.
222, 226, 596 A.2d 365, 368 (1991), in which we held that a defendant may expressly waive the
right to seek sentence reconsideration as part of a plea agreement. Again, it is not clear how this
holding supports defendant’s position in this case.
8
offender enhancement, and defendant acknowledged he understood this before pleading no contest

to the charge. The written plea agreement defendant signed expressly tied the obstruction-of-

justice charge and the habitual-offender enhancement together, and defendant executed the plea

agreement. There is no claim here that his agreement was not knowing and voluntary. On this

record, I agree that he waived his challenge to the validity of the prior convictions.

¶ 20. One consequence of this decision is that, given our related case law concerning

challenges to prior convictions that are used for sentence enhancement, it is not entirely clear

whether and how a defendant who has no defense to the immediate charge, but does challenge

prior convictions supporting a sentence enhancement, can preserve the challenge without forcing

an unnecessary trial on the immediate charge. In State v. Boskind, 174 Vt. 184, 807 A.2d 358

(2002), this Court considered whether defendants facing DUI charges subject to enhancement on

account of prior convictions could challenge those prior convictions in the criminal division in the

context of the pending new DUI charges. Over a dissent, this Court concluded that the defendants

were not entitled to challenge their prior convictions at the sentencing phase of an enhancement

charge; instead, they had to pursue PCR from the enhanced sentence. 174 Vt. at 189-92, 807 A.2d

at 363-65. We acknowledged this authority more recently in In re Manning, 2016 VT 53, ¶ 20,

202 Vt. 111, 147 A.3d 645.

¶ 21. If this is an accurate description of our law, then a defendant with no defense to the

immediate charge, but a potentially meritorious challenge to an underlying conviction used for

enhancement, is forced to contest (rather than plead guilty or no contest to) the immediate charge

in order to avoid a waiver, but is simultaneously precluded from challenging the underlying prior

convictions in the criminal proceeding. It’s incongruous to suggest that a defendant cannot

challenge prior underlying convictions in defending a criminal charge that includes an

enhancement based on those convictions, while at the same time holding that pleading guilty or no

contest to that criminal charge that includes an enhancement constitutes a waiver of any challenges

9
to those convictions—challenges that could not in any event have been prosecuted in the context

of the proceeding culminating in the no contest plea. For that reason, I am not persuaded that our

decision in this appeal is entirely consistent with our existing case law concerning the proper

mechanism for challenging the validity of prior convictions that are integral to new charges. I

concur with the majority because I conclude that either potential holding in this case may be in

tension with existing case law and may ultimately require us to revisit established practices.

Associate Justice

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