PUBLISHED

UNITED STATES COURT OF APPEALS

FOR THE FOURTH CIRCUIT

No. 15-6832

RONALD DONALD DINGLE,

Petitioner - Appellant,

v.

WARDEN ROBERT M. STEVENSON,

Respondent - Appellee.

Appeal from the United States District Court for the District of 

South Carolina, at Florence. Bruce H. Hendricks, District 

Judge. (4:13-cv-02487-BHH)

Argued: September 20, 2016 Decided: October 25, 2016

Before WILKINSON, MOTZ, and HARRIS, Circuit Judges.

Affirmed by published opinion. Judge Wilkinson wrote the 

opinion, in which Judge Motz and Judge Harris joined.

ARGUED: Stephen J. van Stempvoort, MILLER JOHNSON, Grand Rapids, 

Michigan, for Appellant. Alphonso Simon, Jr., OFFICE OF THE 

ATTORNEY GENERAL OF SOUTH CAROLINA, Columbia, South Carolina, 

for Appellee. ON BRIEF: Alan Wilson, Attorney General, John W. 

McIntosh, Chief Deputy Attorney General, Donald J. Zelenka, 

Assistant Deputy Attorney General, OFFICE OF THE ATTORNEY 

GENERAL OF SOUTH CAROLINA, Columbia, South Carolina, for 

Appellee.
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WILKINSON, Circuit Judge:

More than twenty years ago, Ronald Donald Dingle was 

indicted for murder and a host of other crimes committed while 

he was a minor. The state of South Carolina intended to seek the 

death penalty against him, and Dingle pled guilty in exchange 

for a life sentence with the opportunity for parole.

Dingle now seeks to challenge the validity of his guilty 

plea and appeals the district court’s denial of relief on his 28 

U.S.C. § 2254 petition. We granted a certificate of 

appealability on the limited issue of whether Roper v. Simmons, 

543 U.S. 551 (2005), which invalidated the death penalty for 

juvenile offenders, may be applied retroactively to invalidate 

Dingle’s guilty plea. We hold that Roper does not provide an 

avenue for relief and affirm the district court’s dismissal of 

his federal habeas petition. 

I.

While the procedural posture of this case is something of a 

tangle, the facts relevant to the issue on which we granted the 

certificate are relatively straightforward. 

On March 15, 1993, Dingle, a seventeen-year-old juvenile at 

the time of the offense, was charged by the state of South 

Carolina with murder, assault and battery with intent to kill, 

first-degree burglary, kidnapping, pointing a firearm, two 

counts of possession of a weapon during a violent crime, and two 
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counts of possession of a sawed-off shotgun. The state filed a 

notice of intent to seek the death penalty, and on April 17, 

1995, Dingle pled guilty to all the charges in exchange for life 

imprisonment with the possibility of parole. Although the trial 

judge sentenced Dingle to consecutive terms of imprisonment 

following the initial life sentence for murder, all parties 

agreed that Dingle should be eligible for parole after thirty 

years. 

As it turned out, however, the consecutive nature of 

Dingle’s sentences precluded any possibility of parole. Dingle 

filed an application for post-conviction relief (“PCR”), 

asserting that the prospect of parole eligibility was an 

integral element of the plea bargain. On December 5, 1997, the 

PCR court vacated the sentences and remanded “for sentencing

consistent with the intent of the plea agreement or for a new 

trial.” J.A. 338.

After several years went by without a hearing, Dingle filed 

a motion for speedy trial in the Sumter County Court of General 

Sessions. In the meantime, the Supreme Court decided Roper v. 

Simmons, 543 U.S. 551 (2005), which held that imposing capital 

punishment on juvenile offenders was a violation of the Eighth 

Amendment. At the hearing on July 28, 2005, Dingle argued that 

he should be allowed to withdraw his guilty plea because, in 
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light of Roper, he no longer received the benefit of a bargain 

premised on avoiding the death penalty. 

The Court of General Sessions rejected Dingle’s request for 

a new trial. Rather, the court determined that the plea should 

be evaluated based on the law as it existed in 1995 – the court 

could give him the benefit of his bargain by restructuring the 

sentence such that he would be eligible for parole after thirty 

years. Dingle appealed and the South Carolina Supreme Court 

rejected the claim that Roper deprived him of the benefit of his 

plea deal. State v. Dingle, 659 S.E.2d 101, 106 (S.C. 2008).

On January 8, 2009, Dingle filed a second application for 

PCR. This time, he argued that Roper applied retroactively to 

his case and that his guilty plea was involuntary because it was 

made for the sole purpose of avoiding cruel and unusual 

punishment. The PCR court found that the essence of Dingle’s 

Roper claim was already raised and ruled upon by the South 

Carolina Supreme Court. Accordingly, it was barred by res 

judicata. Dingle unsuccessfully appealed the PCR court’s order, 

and filed a third application for PCR that was later dismissed. 

Dingle also filed a petition under 28 U.S.C. § 2254 for a 

writ of habeas corpus in the United States District Court for 

the District of South Carolina. In his petition, Dingle raised 

four claims of error. On November 10, 2009, the district court 

dismissed the claims without prejudice. 
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On September 13, 2013, Dingle filed the instant § 2254 

petition. He contested his conviction on six grounds, including 

various assertions of ineffective assistance of counsel and 

prosecutorial misconduct. The magistrate judge recommended 

denying the petition in its entirety, rejecting some of the 

claims on the merits and finding that others were procedurally 

defaulted. The district court adopted the magistrate judge’s 

report and recommendation and denied relief on Dingle’s § 2254 

petition. This court granted a certificate of appealability on a 

single issue: “whether Roper v. Simmons, 543 U.S. 551 (2005), 

may be applied retroactively to invalidate Dingle’s guilty plea 

where, pre-Roper, he allegedly pled guilty to avoid the death 

penalty.” We denied a certificate as to all other claims. 

II.

Dingle’s primary contention is that his guilty plea should 

be abrogated in light of Roper’s holding that the death penalty 

may not be imposed on juvenile offenders. He asserts, first, 

that Roper articulated a substantive rule that applies 

retroactively to his case, see Montgomery v. Louisiana, 136 S. 

Ct. 718, 734 (2016) (“Miller is no less substantive than are 

Roper and Graham.”), and, second, that if the state cannot seek 

the death penalty against him now, it was improper for the state 

to do so in 1995. Accordingly, because the plea agreement was 
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motivated by a desire to avoid cruel and unusual punishment, 

Dingle argues that his plea was involuntary and invalid. 

In resolving this question, we reiterate that this appeal 

does not raise such issues as ineffective assistance of counsel 

or prosecutorial misconduct in the plea negotiations. The court 

was careful to limit the certificate of appealability to the 

Roper claim and to deny a certificate to all remaining claims, 

many of which are better suited for and have been addressed in 

other proceedings. The case that comes before us is a pure 

question of law: whether Roper, of its own force as a 

substantive rule, applies retroactively to undo a guilty plea. 

There are several difficulties with this argument, which we 

address in turn.*

A.

The Supreme Court in Roper announced a distinct 

constitutional rule prohibiting the imposition of the death 

penalty on juvenile offenders. Roper, 543 U.S. at 568. In so 

doing, however, the Court was careful to limit the scope of this 

 * The state argues that AEDPA’s deferential standard of 

review governs this action. AEDPA, however, applies only to 

claims that have been “adjudicated on the merits in State court 

proceedings,” 28 U.S.C. § 2254(d) (2012), and there is some 

dispute as to whether South Carolina courts actually decided 

Dingle’s Roper claim on the merits. Because we would affirm the 

district judge in all events, we will apply de novo review to 

this case. 
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constitutional bar to the “most severe punishment” of a capital 

sentence, where the Eighth Amendment applies with “special 

force.” Id. The Court therefore made clear that its holding 

should be construed to apply only to the sentence actually at 

issue in that case, which was capital punishment.

Dingle nonetheless argues that Roper is a substantive rule 

and should apply retroactively to invalidate his guilty plea. 

This contention, however, compares apples and oranges. We 

readily grant that Roper announced a substantive rule, but that 

does not decide the outcome of the case at hand. The inescapable 

fact is that Dingle did not receive the death penalty. Nor did 

he receive a life sentence without parole. See Miller v. 

Alabama, 132 S. Ct. 2455 (2012). Rather, Dingle received a life 

sentence with the possibility of parole after thirty years. In 

essence, Dingle seeks to extrapolate from the distinct 

constitutional right recognized in Roper to a much broader 

substantive rule that extends to plea agreements negotiated in 

the shadow of the death penalty. 

The district court correctly found that Roper did not apply 

to situations where a defendant pled guilty to a non-capital 

sentence to avoid the possibility of a capital sentence. Dingle 

v. Stevenson, 772 F. Supp. 2d 734, 740 (D.S.C. 2009). The death 

penalty here operated only as part of the calculus in the plea 

negotiations, and acknowledging that Roper might have altered 
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the calculus is a far cry from finding that its substantive rule 

applies. It happens in the ordinary give and take of a plea 

bargain that a substantive rule may indirectly bear on the 

outcome of the negotiation. Yet the Supreme Court has not 

suggested that a substantive rule would stretch beyond the 

proscribed sentence to reopen guilty pleas with a different 

sentence. See Montgomery v. Louisiana, 136 S. Ct. 718 (2016). 

Rather, when a defendant pleads guilty based on the strength of 

the state’s case and an assessment of the range of penalties to 

which he might otherwise be exposed, we have been especially 

reluctant to rescind the bargain. See United States v. Fugit, 

703 F.3d 248, 253 (4th Cir. 2012) (citing United States v. 

Dominguez Benitez, 542 U.S. 74, 82-83 (2004)). Pleading guilty 

typically entails a deliberate choice to accept the risks and 

rewards of a deal, and that decision may not be casually set 

aside on the basis of buyer’s remorse.

B.

This precise principle was put in play in Brady v. United

States, 397 U.S. 742 (1970). There, as here, a criminal 

defendant was death eligible and entered into a plea agreement

to avoid capital punishment. Subsequent legal developments would 

have made the defendant ineligible for the death penalty, and 

the defendant urged on that basis that he be permitted to 

withdraw his plea. Id. at 756 (citing United States v. Jackson, 
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390 U.S. 570 (1968)). The Court rejected that contention, and 

its language is worth quoting because it is highly pertinent 

here: 

Often the decision to plead guilty is heavily 

influenced by the defendant’s appraisal of the 

prosecution’s case against him and by the apparent 

likelihood of securing leniency should a guilty plea 

be offered and accepted. Considerations like these 

frequently present imponderable questions for which 

there are no certain answers; judgments may be made 

that in the light of later events seem improvident, 

although they were perfectly sensible at the time.

Id. at 756-57.

 And again: 

The rule that a plea must be intelligently made to be 

valid does not require that a plea be vulnerable to 

later attack if the defendant did not correctly assess 

every relevant factor entering into his decision. . . 

. More particularly, absent misrepresentation or other 

impermissible conduct by state agents, a voluntary 

plea of guilty intelligently made in the light of the 

then applicable law does not become vulnerable because 

later judicial decisions indicate that the plea rested 

on a faulty premise.

Id. at 757 (citation omitted).

 And again:

The fact that Brady did not anticipate United States 

v. Jackson does not impugn the truth or reliability of 

his plea. We find no requirement in the Constitution 

that a defendant must be permitted to disown his 

solemn admissions in open court that he committed the 

act with which he is charged simply because it later 

develops that the State would have had a weaker case 

than the defendant had thought or that the maximum 

penalty then assumed applicable has been held 

inapplicable in subsequent judicial decisions.

Id. (citation omitted).
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Brady is remarkable not only for the fact that the Court 

emphatically repeated its holding, but that it managed to drive 

the point home in so many different ways. Dingle tries to assert 

that the coercion involved in his plea negotiation was uniquely 

debilitating because he “knuckl[ed] under threat” of what we now 

understand to be cruel and unusual punishment. App. Br. at 24.

But the logic in Brady applies generally, regardless of the 

reason that a defendant is no longer death eligible. See Brady, 

397 U.S. at 755 (“[A] plea of guilty is not invalid merely 

because entered to avoid the possibility of a death penalty.”).

Contracts in general are a bet on the future. Plea bargains 

are no different: a classic guilty plea permits a defendant to 

gain a present benefit in return for the risk that he may have 

to forego future favorable legal developments. Dingle received 

that present benefit – avoiding the death penalty and life 

without parole - under the law as it existed at the time. 

Although Roper, in hindsight, altered the calculus underlying 

Dingle’s decision to accept a plea agreement, it does not 

undermine the voluntariness of his plea. Some element of 

pressure exists in every deal, as the tradeoff between present 

certainty and future uncertainty is emblematic of the process of 

plea bargaining. Brady makes all that exceptionally clear and in 

following its teachings we find no infirmity in the plea that 

Dingle entered.
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III.

 The judgment of the district court is accordingly 

AFFIRMED.