PRESENT: Lemons, C.J., Goodwyn, McClanahan, Powell, Kelsey, and McCullough, JJ., and 

Millette, S.J.

COMMONWEALTH OF VIRGINIA

 OPINION BY

v. Record No. 160952 JUSTICE ELIZABETH A. McCLANAHAN

 October 19, 2017 

GREGORY EDWARD LEONARD, II

FROM THE COURT OF APPEALS OF VIRGINIA

Gregory Edward Leonard II was convicted of driving under the influence (“DUI”), third 

or subsequent offense within a five-year period. The Court of Appeals vacated the sentence for 

DUI, third offense, and remanded the case to the trial court for sentencing on DUI, second 

offense. The Court of Appeals ruled that the Commonwealth was collaterally estopped in this 

case from using a valid DUI conviction as a predicate offense for sentencing enhancement

because a general district court, in an unrelated case, previously ruled that the Commonwealth 

could not use the same DUI conviction as a predicate offense for sentencing enhancement. We 

conclude the Court of Appeals erred in applying the doctrine of collateral estoppel, and therefore, 

we will reverse the judgment of the Court of Appeals.

I. BACKGROUND

 A grand jury indicted Leonard for driving under the influence, in violation of Code § 

18.2-266, third or subsequent offense within five years, in connection with an accident that 

occurred on March 26, 2012. See Code § 18.2-270(C)(1).1

 At a bench trial in the circuit court, 

 1

 Code § 18.2-270(C)(1) states:

Any person convicted of three offenses of § 18.2-266 committed within a 10-year 

period shall upon conviction of the third offense be guilty of a Class 6 felony. 

The sentence of any person convicted of three offenses of § 18.2-266 committed 
2

the Commonwealth introduced certified copies of DUI conviction orders entered in 2010 and 

2012 to establish that Leonard had committed three DUI offenses within a five-year period.2

 

The 2010 conviction order was entered by the General District Court of the City of Virginia 

Beach and recited that Leonard was present at trial, was represented by counsel, and pled guilty 

to the charge of DUI, first offense.

3

 The 2012 conviction order was entered by the Circuit Court 

of the City of Virginia Beach, which heard the matter on appeal from the general district court, 

and recited that Leonard was present at trial, was represented by counsel, and pled guilty to the 

charge of DUI, first offense.

 Although Leonard did not object to the admission into evidence of the 2012 conviction 

order, Leonard asserted that the principle of collateral estoppel precluded the Commonwealth 

from relying upon the 2010 conviction order. Leonard claimed that the General District Court of 

the City of Virginia Beach, in the 2012 case that was later appealed to the circuit court, ruled that 

the Commonwealth could not rely upon the 2010 DUI conviction for sentencing enhancement. 

Leonard introduced a certified copy of the conviction order entered by the general district court 

 

within a 10-year period shall include a mandatory minimum sentence of 90 days, 

unless the three offenses were committed within a five-year period, in which case 

the sentence shall include a mandatory minimum sentence of confinement for six 

months. In addition, such person shall be fined a mandatory minimum fine of 

$1,000. 

2 The Commonwealth also admitted into evidence a copy of the transcript of Leonard’s 

driving record from the Virginia Department of Motor Vehicles, which listed the two prior 

convictions for DUI in 2010 and 2012. Leonard’s 2010 DUI conviction was for an offense that 

occurred on April 21, 2010. Leonard’s 2012 DUI conviction was for an offense that occurred on 

March 16, 2012. 

3

 The conviction order is a preprinted form disposition order located on the back of the 

arrest warrant and contains a series of blocks that may be checked by the court. A separate form 

conviction and sentencing order was incorporated as well.
3

in 2012, which noted that Leonard had been charged with DUI, second offense, but found guilty 

of DUI, first offense. Leonard argued that the general district court ruled in 2012 that the 

Commonwealth could not introduce the 2010 DUI conviction to establish DUI, second offense, 

because it found that Leonard had not been advised of his constitutional rights, in violation of 

Boykin v. Alabama, 395 U.S. 238, 242 (1969), before pleading guilty to the 2010 offense.

4

Leonard maintained that because the issue of whether the Commonwealth could rely 

upon the 2010 DUI conviction for sentencing enhancement had been previously determined in 

the 2012 general district court proceeding, the Commonwealth was precluded, under the 

principle of collateral estoppel, from relitigating this issue. Specifically, Leonard asserted that 

“[t]he issue there that was litigated was whether or not the 2010 conviction could be introduced 

to enhance [the first offense to] a second offense” and that “the Commonwealth is trying to 

relitigate that same issue to try to use the 2010 [conviction] to make this a third offense.”

 The Commonwealth responded to Leonard’s argument by noting that the general district 

court’s order did not provide a basis for the reduction of DUI, second offense, to DUI, first 

offense, and that in any event, the general district court’s judgment was annulled once the matter 

was appealed to the circuit court. Upon the conclusion of the evidence, however, the 

 4 In Boykins, the United States Supreme Court held it was error for a trial court to accept 

a criminal defendant’s guilty plea without an affirmative showing that the plea was knowingly 

and voluntarily made. 395 U.S. at 242. According to Leonard, the general district court’s 2012 

finding that he had not been advised of his constitutional rights before pleading guilty in 2010 

was based on the general district court’s failure in 2010 to note on the warrant that the plea was 

“voluntarily and intelligently entered after the defendant was apprised of his right against 

compulsory self-incrimination and his right to confront the witnesses against him.”
4

Commonwealth stipulated that the basis for the general district court’s 2012 ruling was its 

finding that Leonard was not advised of his constitutional rights before pleading guilty in 2010.5

 The trial court overruled Leonard’s objection to the admission of the 2010 DUI 

conviction order and found Leonard guilty of DUI, third or subsequent offense, but permitted the 

parties to brief the issue of collateral estoppel prior to sentencing.6 At the sentencing hearing, 

the trial court ruled that collateral estoppel did not apply to preclude the Commonwealth’s 

reliance on the 2010 DUI conviction as a predicate offense for sentencing enhancement. The 

trial court stated that Leonard “failed to prove two of the elements, litigation of the issue and

final judgment on the merits.”

 Leonard appealed to the Court of Appeals, which vacated the trial court’s judgment and 

held that the Commonwealth was barred under the doctrine of collateral estoppel from using the 

2010 DUI conviction as a predicate offense under the enhanced penalty provisions of Code § 

18.2-270(C)(1).7 Leonard v. Commonwealth, 66 Va. App. 270, 294, 784 S.E.2d 315, 327 

 5 The Commonwealth stated as follows: 

I’ll stipulate. I – it’s my understanding that that was the reason for why 

Judge Hutchens reduced the charges to a DUI first. I don’t think there’s any 

evidence before the court. I will make it evidence now as part of that 

stipulation that Judge Hutchens reduced that because she did not find that 

first prior to be – I wasn’t there.

6

 Leonard was also found guilty of driving on a suspended license. That conviction is not 

before us on appeal. 

7

 Additionally, the Court of Appeals ruled that the evidence was sufficient to support the 

trial court’s holding that Leonard was guilty of DUI in violation of Code § 18.2-266 for the 

offense that occurred on March 26, 2012, and that Code § 18.2-270(C) does not require a person 

to be sentenced for DUI, second offense, before being sentenced for DUI, third or subsequent 

offense. As to the latter ruling, the Court of Appeals stated that “[n]othing in Code § 18.2-

270(B) or anywhere else in Code § 18.2-270 suggests that the prior imposition of punishment 

under Code § 18.2-270(B) is required before a defendant can be punished under Code § 18.2-
5

(2016). Initially, the Court of Appeals observed that “[a]ssuming” the general district court in 

the 2012 proceeding concluded that the 2010 DUI conviction was “somehow invalid,” “its 

actions were an impermissible collateral review of a valid conviction.” Id. at 288, 784 S.E.2d at 

324.8 Nevertheless, the Court of Appeals concluded that Leonard was entitled to rely on the 

general district court’s 2012 ruling, though made in error, because the Commonwealth’s 

stipulation established that the validity of the 2010 DUI conviction was actually litigated in the 

2012 general district court proceeding and that ruling was not nullified by the appeal to the 

circuit court. Id. at 291-94, 784 S.E.2d at 326-27. Finding the evidence insufficient to support 

Leonard’s conviction for DUI, third offense, the Court of Appeals remanded the case to the trial 

court for Leonard to be sentenced for DUI, second offense. Id. at 294-95, 784 S.E.2d at 327. 

II. ANALYSIS

 On appeal to this Court, the Commonwealth contends that the Court of Appeals erred in 

holding that collateral estoppel barred the Commonwealth from introducing Leonard’s 2010 DUI 

conviction order for sentencing enhancement. We apply a de novo standard of review to the 

 

270(C)(1). Although that may be the ‘normal’ progression of events, Code § 18.2-270(C)(1) 

only requires that there have been two previous convictions for DUI in violation of Code § 18.2-

266.” Leonard v. Commonwealth, 66 Va. App. 270, 286 n.4, 784 S.E.2d 315, 323 n.4 (2016). 

8

 The Court of Appeals noted that “[f]rom the face of the June 2010 warrant/conviction 

order, it is clear that appellant appeared in court, where he was represented by counsel, and was 

convicted of DUI in violation of Code § 18.2-266. He did not challenge that conviction by way 

of direct appeal or other post-conviction proceeding.” Leonard, 66 Va. App. at 287, 784 S.E.2d 

at 323. Recognizing that “the right to collaterally attack a prior criminal conviction in a 

subsequent proceeding for enhancement purposes is limited to the actual denial of counsel,” 

Vester v. Commonwealth, 42 Va. App. 592, 597, 593 S.E.2d 551, 553 (2004) (emphasis in 

original), the Court of Appeals stated that “it was error for the general district court even to 

entertain a collateral attack on the validity of that conviction in 2012.” Leonard, 66 Va. App. at 

288, 784 S.E.2d at 324. 
6

issue of whether the principle of collateral estoppel is applicable in a given case. Commonwealth 

v. Davis, 290 Va. 362, 368, 777 S.E.2d 555, 558 (2015). 

In Ashe v. Swenson, 397 U.S. 436 (1970), the United States Supreme Court “incorporated 

the doctrine of collateral estoppel into the Fifth Amendment proscription against double 

jeopardy.” Clodfelter v. Commonwealth, 218 Va. 98, 105, 235 S.E.2d 340, 344 (1977), rev’d on 

other grounds, 218 Va. 619, 238 S.E.2d 820 (1977). The principle of collateral estoppel “means 

simply that when an issue of ultimate fact has once been determined by a valid and final 

judgment, that issue cannot again be litigated between the same parties in any future lawsuit.” 

Ashe, 397 U.S. at 443. See also Funny Guy, LLC v. Lecego, LLC, 293 Va. 135, 142, 795 S.E.2d 

887, 890 (2017) (“Under the concept of collateral estoppel, ‘the parties to the first action and 

their privies are precluded from litigating [in a subsequent suit] any issue of fact actually 

litigated and essential to a valid and final personal judgment in the first action.’”) (quoting 

Rawlings v. Lopez, 267 Va. 4, 4-5, 591 S.E.2d 691, 692 (2004)). In the criminal context, the 

principle of collateral estoppel “protects the accused from attempts to relitigate the facts 

underlying a prior acquittal.” Brown v. Ohio, 432 U.S. 161, 165 (1977). The defendant bears the 

burden of proving that the precise issue of fact sought to be precluded was raised and determined 

in the prior action. Rhodes v. Commonwealth, 223 Va. 743, 749, 292 S.E.2d 373, 376 (1982). 

 Collateral estoppel, as applied in criminal proceedings, becomes applicable only when 

the defendant’s prior acquittal necessarily resolved a factual issue that the Commonwealth seeks 

to litigate again in a subsequent proceeding.9

 See, e.g., Yeager v. United States, 557 U.S. 110, 

 9

 Although collateral estoppel, as a general principle, has been described as barring 

relitigation of an issue of fact or law, see Bravo-Fernandez v. United States, 580 U.S. ___, ___, 

137 S. Ct. 352, 358 (2016), the United States Supreme Court has been more circumspect in 

applying the doctrine of collateral estoppel in criminal cases, noting the absence of appellate 
7

123 (2009) (holding that “[i]f the possession of insider information was a critical issue of 

ultimate fact in all of the charges against petitioner, a jury verdict that necessarily decided that

issue in his favor protects him from prosecution for any charge for which that is an essential 

element”); Ashe, 397 U.S. at 445-46 (holding that where the jury found, in a prior prosecution of 

robbery of one victim, that the accused was not one of the robbers, the State was collaterally 

estopped to litigate that factual issue again in subsequent prosecution for different victim of same 

robbery); Davis, 290 Va. at 371-72, 777 S.E.2d at 559-60 (holding that where the identity of the 

shooter was the “issue of ultimate fact that was actually and necessarily decided” in defendant’s 

favor in prior proceeding, the Commonwealth was collaterally estopped from relitigating that 

“specific fact”); Rhodes, 223 Va. at 749-50, 292 S.E.2d at 377 (holding that because defendant 

was unable to prove that “the precise issue of fact,” i.e., presence of PCP in defendant’s vehicle,

was determined in his favor, that issue of fact remained “unfettered by the doctrine of collateral 

estoppel”); Simon v. Commonwealth, 220 Va. 412, 418-19, 258 S.E.2d 567, 572 (1979) (holding 

that where the factual issue of defendant’s intoxication was determined in his favor in a prior 

proceeding, Commonwealth was collaterally estopped from again litigating issue of defendant’s 

intoxication); Lee v. Commonwealth, 219 Va. 1108, 1111, 254 S.E.2d 126, 127 (1979) (holding 

that whether defendant was driving his car on the date charged in the warrant was “an issue of 

ultimate fact” determined in prior proceeding to which collateral estoppel applied); Clodfelter,

218 Va. at 108, 235 S.E.2d at 346 (holding that collateral estoppel did not apply where defendant 

failed to satisfy his burden of showing that “the precise factual issue or question which he now 

seeks to preclude,” i.e., possession of drugs, was necessarily decided in prior proceeding). 

 

review of acquittals and the limited avenues available to the government to correct legal errors, 

see, e.g., Standefer v. United States, 447 U.S. 10, 22-25 (1980). 
8

The determination of whether collateral estoppel applies here, therefore, depends on 

whether the Commonwealth is attempting to litigate in this case an issue of fact that was resolved 

in Leonard’s favor in the 2012 proceeding. When the general district court ruled in 2012 that the 

Commonwealth could not use the 2010 conviction to support DUI, second offense, the factual 

question it decided in Leonard’s favor was that Leonard had not been advised of his 

constitutional rights prior to pleading guilty to the 2010 DUI. That fact has no bearing on the 

issues in this case and is not a question the Commonwealth is seeking to litigate. Leonard did 

not argue in the trial court that the 2010 DUI conviction order was inadmissible because he was 

not advised of his rights prior to entering his guilty plea in the 2010 proceeding.10 Instead, he 

argued that the 2010 DUI conviction order was inadmissible in this case because it was ruled 

inadmissible in the 2012 proceeding.

11

 In other words, Leonard is not seeking to preclude the Commonwealth from relitigating a 

factual finding made in the 2012 proceeding, but is attempting to bind the Commonwealth to an 

evidentiary ruling made in the 2012 proceeding in connection with sentencing on a different 

offense. To the extent the general district court actually concluded the 2010 conviction was 

 10 Indeed, Leonard had no viable legal ground to collaterally attack the 2010 DUI 

conviction. Only convictions obtained in violation of the Sixth Amendment right to counsel are 

subject to collateral attack in recidivist proceedings. See Johnson v. United States, 544 U.S. 295, 

303-04 (2005); Daniels v. United States. 532 U.S. 374, 378 (2001); Custis v. United States, 511 

U.S. 485, 496 (1994); see also Vester, 42 Va. App. at 597, 593 S.E.2d at 553. 

11 The Court of Appeals held that “the stipulation in this case established the basis for the 

general district court’s 2012 ruling, and therefore, [Leonard] sufficiently demonstrated that the 

fact was actually litigated and resolved in his favor in the prior proceeding.” Leonard, 66 Va. 

App. at 291, 784 S.E.2d at 326. In so holding, the Court of Appeals viewed the answer in this 

case as resting on the ability to discern the basis for the general district court’s 2012 ruling and 

treated “the fact” litigated and resolved in Leonard’s favor as a determination of fact at issue in 

this case.
9

constitutionally invalid for purposes of sentencing enhancement under Code § 18.2-270, any 

such conclusion was a determination of law, see, e.g., Montgomery County v. Virginia Dep’t of 

Rail & Pub. Transp., 282 Va. 422, 435, 719 S.E.2d 294, 300 (2011) (stating that “constitutional 

arguments are questions of law”), based on resolution of a factual question that is not at issue in 

this case.

 As discussed previously, the application of collateral estoppel in the criminal context has 

been confined to attempts by the government to relitigate the facts underlying a prior acquittal. 

To be sure, the 2010 DUI conviction remains a valid and existing conviction. The general 

district court’s ruling in 2012 did “not operate to ‘acquit’ [Leonard] of [the 2010] conviction or 

change the fact that the prior conviction does still exist.” Baker v. State, 425 N.E.2d 98, 101 

(Ind. 1981) (holding that collateral estoppel did not bar the State from using prior felony 

convictions in support of an habitual offender charge where defendant had previously been 

acquitted of an habitual offender charge based on the same prior felony convictions). See also

Wright v. People, 690 P.2d 1257, 1261 (Colo. 1984) (holding that in the context of habitual 

criminality proceedings, collateral estoppel does not apply to trial court rulings excluding 

evidence of defendant’s prior conviction on the basis that the plea hearing was constitutionally 

inadequate); Hall v. State, 405 N.E.2d 530, 536-37 (Ind. 1980) (holding that collateral estoppel 

does not apply to preclude the State from relying on prior felony convictions, still existing, 

where trial court, at previous hearing, dismissed an habitual offender count for insufficient 

evidence of knowing and voluntary guilty pleas). The double jeopardy concerns arising from 

attempts by the government to relitigate facts underlying a prior acquittal do not apply to the use 

of a valid and existing conviction for enhanced sentencing. 
10

 Therefore, the Court of Appeals erred in holding that the doctrine of collateral estoppel 

applied to preclude the Commonwealth from using the 2010 DUI conviction as a predicate 

offense under the penalty provisions of Code § 18.2-270(C)(1).12

III. CONCLUSION

 For the foregoing reasons, we will reverse the judgment of the Court of Appeals and 

reinstate the trial court’s order of conviction on DUI, third or subsequent offense within a fiveyear period. 

Reversed and final judgment. 

 

12 The Commonwealth also argues that the Court of Appeals erred in holding that the 

general district court’s ruling in 2012 was not nullified by the appeal of the general district 

court’s judgment to the circuit court. Relying on Turner v. Commonwealth, 49 Va. App. 381, 

641 S.E.2d 771 (2007), the Court of Appeals concluded that the general district court’s 2012 

ruling regarding the validity of the 2010 DUI conviction was a final judgment. Given our 

holding that the Commonwealth is not seeking to litigate a factual issue to which collateral 

estoppel applies, it is unnecessary for us to address the Commonwealth’s argument.