By Ali Fenno

On October 25, 2016, the Fourth Circuit issued a published opinion in the criminal case of Dingle v. Stevenson. In Dingle, the Fourth Circuit addressed whether the Supreme Court’s holding in Roper v. Simmons, which invalidated the use of capital punishment against juvenile offenders, should apply retroactively to undo a guilty plea made by Ronald Donald Dingle (“Dingle”). After examining the scope of the holding in Roper and the nature of plea bargains, the Fourth Circuit held that Roper cannot apply retroactively to undo a guilty plea and affirmed the lower court’s dismissal of Dingle’s petition.

Lower Courts Repeatedly Dismiss Dingle’s Petitions

In 1993 the state of South Carolina (the “State”) charged Dingle 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 counts of possession of a sawed-off shotgun. Because the State intended to pursue the death penalty, Dingle plead guilty in exchange for life imprisonment with the possibility of parole.

When it was later discovered that the consecutive nature of Dingle’s sentences precluded parole, an integral part of the plea bargain, Dingle filed an application for post-conviction relief (“PCR”). The PCR court vacated his sentences and remanded for sentencing consistent with the intent of the plea agreement or for a new trial.

Several years later, a hearing still had not been held, so Dingle filed a motion for a speedy trial. The hearing was then held on July 28, 2005, and Dingle contended that his guilty plea should be withdrawn. He argued that the benefit of his plea bargain, avoiding the death penalty, was removed by the Supreme Court’s recent decision in Roper, which held that it was a violation of the Eighth Amendment for the death penalty to be used against juvenile offenders. The Court of General Sessions disagreed, rejecting Dingle’s request for a new trial and holding that pleas should be evaluated based on the law that existed in 1995. The South Carolina Supreme Court affirmed this decision, finding that Roper did not remove the benefit of the plea bargain.

Dingle again filed an application for PCR in 2009, arguing that Roper retroactively applied to his case and, as such, his guilty plea was involuntary because it was made to avoid cruel and unusual punishment. However, the PCR court found that Dingle’s claim was barred by res judicata. Dingle’s subsequent appeal and third petition were unsuccessful.

Dingle also filed a petition for a writ of habeas corpus under 28 U.S.C. § 2554 in the United States District Court for the District of South Carolina. He raised four claims of error, but the district court dismissed the claims without prejudice.

On September 13, 2013, Dingle filed the instant § 2554 petition. The petition contested Dingle’s conviction on six grounds, but the district court adopted the magistrate judge’s recommendation to deny the petition in its entirety.

Issues on Appeal

The Fourth Circuit granted a certificate of appealability to determine the single issue of whether Roper may be applied retroactively to invalidate Dingle’s guilty plea. Dingle argued that the holding in Roper invalidated his guilty plea because (1) it was a substantive rule so applied retroactively to his case, and (2) if it would be improper for the state to seek the death penalty against him now, then it was also improper in 1995. Thus, his plea was invalid because it was attempt to avoid cruel and unusual punishment. However, the Fourth Circuit disagreed, concluding that (1) plea bargains are outside the scope of the Roper holding, and (2) the nature of plea bargains support upholding their validity.

Plea Bargains Are Outside the Scope of Roper

The Fourth Circuit first concluded that the holding in Roper was never intended to apply to plea bargains. Although the court conceded that Roper was indeed a substantive rule that could be applied retroactively, it found that the scope of the rule was limited to the actual sentence delivered in a case. Because Dingle did not actually receive the death penalty, attempting to apply the holding in Roper to his own case was “compar[ing] apples and oranges.” The court further noted that the Supreme Court had never before allowed “a substantive rule to stretch beyond the proscribed sentence to reopen guilty pleas with a different sentence.”

Future Legal Developments Cannot Invalidate Plea Bargains

The Fourth Circuit next concluded that the holding in Roper could not invalidate Dingle’s guilty plea because plea bargains are “a bet on the future,” whereby defendants accept both the benefits of a lighter sentence and the risks of losing out on future favorable legal developments. A defendant’s remorse at missing out on those favorable legal developments is not enough to rescind an entire bargain.

The court found support for this contention in Brady v. United States, where the Supreme Court held that a defendant who entered into a plea agreement to avoid capital punishment could not later withdraw his plea agreement when subsequent legal developments made him ineligible for the death penalty. The Supreme Court suggested that defendants who are offered plea bargains must weigh the benefits and risks of such bargains, and the fact that they did not anticipate certain legal developments could not “impugn the truth or reliability of [their] plea.” Accordingly, the Fourth Circuit concluded that when Dingle entered his guilty plea, he accepted the trade-off between present benefits and future risks that is “emblematic” of plea bargains, and his inability to anticipate the favorable outcome in Roper could not invalidate his plea.


The Fourth Circuit concluded that (1) Roper, even applied retroactively, could not invalidate Dingle’s plea, and (2) precedent and policy argued against setting aside Dingle’s plea bargain. Accordingly, it affirmed the district court’s dismissal of Dingle’s petition and held that Roper could not be applied retroactively to invalidate Dingle’s guilty plea.


By Paige Topper

On February 19, 2016, in the criminal case of United States v. Adams, a published opinion, the Fourth Circuit vacated the conviction of defendant, Richard Adams, for being a felon in possession of a firearm because, at the time of the offense, Adams was not a convicted felon.

Adams’ Plea Agreement Relating to a Series of Armed Robberies 

A grand jury indicted Adams for committing a series of armed robberies of convenience stores. Adams entered into a written plea agreement in which he pled guilty to three of eight criminal counts: (1) robbery, (2) using and carrying a firearm during a crime of violence, and (3) being a felon in possession of a firearm. By entering into the plea agreement, Adams waived his right to challenge his conviction or sentence. Adams’ total sentence for the three crimes was 240 months imprisonment.

On August 28, 2012, Adams filed a motion pursuant to 28 U.S.C. § 2255 to vacate his conviction for being a felon in possession of a firearm (§ 922(g)). Adams argued that his prior convictions were not felonies after the decision in United States v. Simmons. In Simmons the Fourth Circuit held that for an offense to be a prior felony a defendant must have actually faced the possibility of more than one year in prison. Therefore, Adams argued he was innocent of being a felon in possession of a firearm (his prior charges were not discussed in the opinion). The district court determined that Adams’ claim was barred by the waiver in his plea agreement. The Fourth Circuit granted Adams a certificate of appealability to determine whether Adams’ waiver barred consideration of his claim that Simmons rendered him innocent of being a felon in possession of a firearm.

Adams Was Not Barred from Bringing Simmons Claim

In order to determine whether Adams was innocent, the Fourth Circuit first examined whether Adams’ Simmons-based claim was within the scope of the valid waiver of his plea agreement. The Fourth Circuit had previously reasoned in case law that it would refuse to enforce an otherwise valid waiver if doing so would result in a “miscarriage of justice.” Specifically, the Fourth Circuit found that a proper showing of actual innocence would constitute a miscarriage of justice should a plea agreement waiver be upheld in light of such innocence. Thus, if the Court determined that Adams made a cognizable claim of actual innocence then his motion falls outside the scope of his waiver.

Adams Properly Alleged his Actual Innocence

The Fourth Circuit then concluded that Adams made a valid claim of actual innocence based on prior case law. The Court turned to Miller v. United States to determine that for defendants convicted of being a felon in possession of a firearm, where the predicate convictions were North Carolina felony offenses for which the defendant could not have received sentences of more than one year in prison, Simmons made clear that such convictions do not qualify as predicate felonies for federal law and that the defendants are thus innocent of the offense.

The Court found the government’s argument that Adams only showed legal innocence as opposed to factual innocence to have no merit. Specifically, the Fourth Circuit determined that Adams did show factual innocence because, by showing that he was not a convicted felon at the time at issue, Adams made it impossible for the government to prove one of the required elements of the crime for possession of a firearm by a convicted felon: that the defendant was a convicted felon at the time of the offense.

Furthermore, the Fourth Circuit found the government’s second argument that Adams had to show that he was also actually innocent of the conduct alleged in the five dismissed counts unpersuasive. The Court explained that a defendant making a claim of actual innocence after a plea deal has to show only that he is factually innocent of the underlying criminal conduct. Thus, Adams did have to prove actual innocence to the five dismissed charges because they related to different criminal conduct.

Fourth Circuit Vacated Conviction

The Fourth Circuit concluded that Adams made the requisite showing of actual innocence for the crime of being a felon in possession of a firearm. Subsequently, the Court vacated Adams’ § 922(g) conviction.

By Whitney Pakalka

On January 28, 2016, the Fourth Circuit published its opinion in the criminal case, United States v. Williams, clarifying when an appellate court may review a prison sentence imposed pursuant to a plea agreement made under Rule 11(c)(1)(C) of the Federal Rules of Criminal Procedure. The Court held that unless the sentence imposed is greater than that set forth in the plea agreement, the sentence will only be reviewable if it is unlawful or is expressly based on the United States Sentencing Guidelines. Because appellant’s plea agreement did not satisfy these criteria, the Court dismissed her attempted appeal of her sentence.

Defendants’ Plea Agreements and Arguments on Appeal

Both David James Williams, III and Kristin Deantanetta Williams separately pleaded guilty to one count of federal conspiracy to possess and distribute cocaine and cocaine base.   Both defendants entered into plea agreements under Rule 11(c)(1)(C), each stipulating that a sentence of 120 months imprisonment was “the appropriate disposition in this case.” The District Court for the District of South Carolina sentenced Defendants in accordance with those agreements.

David Williams and Kristin Williams challenged their convictions on appeal, but only Kristin Williams challenged her sentence. As to the challenged convictions, counsel raised questions as to whether the district court complied with Rule 11 as to both Defendants. The Fourth Circuit rejected this challenge and affirmed both convictions, finding that the District Court fully complied with Rule 11’s requirements. Kristin Williams’ appeal also questioned whether her sentence was reasonable. The Fourth Circuit considered whether it had jurisdiction to review her sentence on appeal.

Appropriate Review of Kristin Williams’s Prison Sentence

As an initial matter, the Fourth Circuit noted that not all sentences are subject to appellate review, and as governed by 18 U.S.C. § 3742(a), an appellate court may review a defendant’s final sentence only if it (1) “was imposed in violation of law,” (2) “was imposed as a result of an incorrect application of the sentencing guidelines,” (3) “is greater than the sentence specified in the applicable guideline range,” or (4) “was imposed for an offense for which there is no sentencing guideline and is plainly unreasonable.” However, as the Fourth Circuit noted, 18 U.S.C. § 3742(c) dictates that when a sentence is imposed under a stipulated plea agreement, the defendant cannot challenge the sentence based on the third or fourth factor unless it exceeds the sentence set forth in the plea agreement.

The Fourth Circuit quickly eliminated three of the four grounds on which Kristin Williams could seek review of her sentence under § 3742(a): the first basis was eliminated because her sentence was not imposed in violation of law; the third and fourth options were unavailable because her sentence was entered pursuant to a Rule 11(c)(1)(C) plea agreement that matched her sentence exactly. This left only the question of whether her sentence was imposed due to an incorrect application of the sentencing guidelines.

The Fourth Circuit wrote that it has suggested on numerous occasions that a sentence imposed pursuant to a Rule 11(c)(1)(C) plea deal is not the result of an incorrect application of the sentencing guidelines by the district court, but is instead based on the parties’ agreement. While some sister circuits follow this approach, others still permit a defendant to appeal a sentence imposed under a stipulated plea if it results from an incorrect application of the guidelines. Yet, despite its previous holdings, the Fourth Circuit chose to consider the issue in light of the Supreme Court’s decision in Freeman v. United States.

Reconsidering Appellate Review of Prison Sentences based on the Supreme Court’s Decision in Freeman v. United States

In Freeman, the Supreme Court held that a stipulated plea agreement can, in some circumstances, be “based on” the sentencing guidelines. Although Freeman was interpreting a different section of the federal code, 18 U.S.C. § 3582(c)(2), which defines a district court’s power to reduce a sentence already imposed, the issue in that case was whether a Rule 11(c)(1)(C) plea agreement was “based on” sentencing guidelines and was therefore reviewable. The Supreme Court held that when a plea “agreement expressly uses a Guidelines sentencing range applicable to the charged offense to establish the term of imprisonment,” the sentence is “based on” the guidelines and is reviewable. The Fourth Circuit applied Freeman’s rule in United States v. Brown, concluding that for purposes of § 3582(c)(2), when a Rule 11(c)(1)(C) plea agreement expressly uses the sentencing guidelines to establish the prison term, the sentence is reviewable.

The Fourth Circuit could find no reason not to extend this logic to the statutory subsection at issue here: “Surely, where a stipulated plea is ‘based on’ the Guidelines and reviewable in . . . subsection 3582(c)(2), it also involves an “application of” the Guidelines and is reviewable under subsection 3742(a)(2).” In addition, the Fourth Circuit found this reading to be in line with the overall operation of § 3742. The Court reasoned that because 3742(c) specifically prohibits appeals of Rule 11(c)(1)(C) sentences under paragraphs (3) and (4), it would stand to reason that appeals are permitted under paragraph (2).   The Fourth Circuit held that when a sentence is imposed pursuant to a Rule 11(c)(1)(C) plea agreement, it may be reviewed only where the sentence is unlawful, the sentence imposed exceeds the term set forth in the plea agreement, or where the agreement expressly used the sentencing guidelines in establishing the prison term.

Kristin William’s Appeal of Her Sentence Dismissed

The Fourth Circuit ultimately found that Kristin Williams’ sentence was not “imposed as a result of an incorrect application of the sentencing guidelines.” Her plea agreement did not use or make reference to a guidelines-based calculation. Thus, under the standard set forth above, her sentence was not properly reviewable, and lacking jurisdiction, the Court dismissed the attempted appeal of her sentence.