Ronald Dingle v. Robert Stevenson, 2016 U.S. App. LEXIS 19258

In 1993 Ronald Dingle, age 17 at the time, was indicted in South Carolina on murder and related charges; the State notified intent to seek the death penalty.
In 1995 Dingle pled guilty in exchange for life imprisonment with parole eligibility after 30 years (plea explicitly to avoid capital exposure).
Due to sentencing structure he could not initially obtain parole; a 1997 PCR court vacated the sentences and ordered resentencing consistent with the plea or a new trial.
After delays and the Supreme Court’s 2005 decision in Roper v. Simmons (juvenile death-penalty bar), Dingle sought to withdraw his plea arguing Roper made his plea involuntary because it was taken to avoid a punishment no longer constitutional.
South Carolina courts denied relief; Dingle filed successive PCRs and a § 2254 habeas petition raising multiple claims. The Fourth Circuit granted COA only on whether Roper applies retroactively to void his guilty plea.
The Fourth Circuit affirmed, holding Roper does not retroactively invalidate a voluntary guilty plea to a non-capital sentence negotiated to avoid capital exposure.

Issue	Dingle's Argument	State's Argument	Held
Whether Roper v. Simmons applies retroactively as a substantive rule to invalidate Dingle’s guilty plea negotiated to avoid the death penalty	Roper is a substantive rule that should apply retroactively; because the plea was made solely to avoid a now-unconstitutional death penalty, the plea is involuntary and must be vacated	Roper’s rule bars only the imposition of capital punishment on juveniles and does not reach non-capital sentences or reopen voluntary guilty pleas entered under then-applicable law	The court held Roper does not provide a basis to undo a voluntary guilty plea to a non-capital sentence; plea voluntariness is judged by law in effect when plea was entered
Whether the fact that the plea was motivated by avoiding the death penalty renders it involuntary under Brady principles	Plea was coerced by threat of a punishment now deemed cruel and unusual, so it was not voluntary	Brady and related precedent sustain guilty pleas entered intelligently under the law at the time, even if later rulings change the defendant’s exposure	The court applied Brady: a plea intelligently made under then-applicable law is not vulnerable merely because later decisions alter the legal landscape

Roper v. Simmons, 543 U.S. 551 (prohibiting capital punishment for juvenile offenders)
Montgomery v. Louisiana, 136 S. Ct. 718 (discussing retroactivity of substantive rules announced in cases like Roper and Miller)
Brady v. United States, 397 U.S. 742 (pleas entered to avoid capital punishment are not automatically invalidated by later changes in law)
Miller v. Alabama, 132 S. Ct. 2455 (Eighth Amendment limits on harsh juvenile sentences; discussed for context on substantive juvenile-sentencing rules)
United States v. Dominguez Benitez, 542 U.S. 74 (plea-related standards; cited for plea finality principles)
United States v. Fugit, 703 F.3d 248 (4th Cir. precedent on reluctance to rescind plea bargains)
Dingle v. Stevenson, 772 F. Supp. 2d 734 (D.S.C. 2009) (district court ruling that Roper did not invalidate plea negotiated to avoid capital exposure)