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Vague Criminality and Mass Incarceration: Will Dimaya End the Insanity?

by Leah Litman, Harvard Law Review Blog

Today [April 17, 2018] the Supreme Court decided Sessions v. Dimaya and struck down the federal definition of “crime of violence” as unconstitutionally vague. The statute, section 16(b) (along with its very analogous cousin, section 924(c)), has meaningfully contributed to mass incarceration, racial disparities in sentencing, and excessive sentencing at the federal level. Dimaya recognized that section 16(b) did so in part through sprawling, amorphous phrasing that could be interpreted and applied in capricious and largely unbounded ways to expand the category of “crime of violence.” The impact of the Dimaya decision is potentially enormous, both for deportations (the case before the Court) and for criminal sentences.

The Court had done something similar in Johnson v. United States, holding the Armed Career Criminal Act’s residual clause unconstitutionally void for vagueness. Now Justice Kagan, writing for the majority in Dimaya, emphatically rejected the government’s plea to keep on keeping on in a futile attempt to try and give section 16(b) meaning:

“The Government would condemn us to repeat the past—to rerun the old ACCA tape, as though we remembered nothing from its first showing. But why should we disregard a lesson so hard learned? “Insanity,” Justice Scalia wrote in the last ACCA residual clause case before Johnson, “is doing the same thing over and over again, but expecting different results.” Sykes, 564 U. S., at 28 (dissenting opinion). We abandoned that lunatic practice in Johnson and see no reason to start it again.”

Dimaya was right to correct a wrong of the past. But while Dimaya may prevent another rerun of the ACCA insanity, it’s not yet clear how many wrongs of the past Dimaya will ultimately right. Whether Dimaya rights wrongful convictions will depend on how courts interpret a slew of procedural restrictions on federal resentencing and federal post-conviction review.

Group 1: Federal Prisoners Whose Convictions Have Not Yet Become Final

Start with federal prisoners whose convictions have not yet become final (that is, their direct appeals to the court of appeals and Supreme Court have not finished). Will the Court’s ruling in Dimaya help them out? Assuming these prisoners have not previously made the argument that section 16(b) is unconstitutionally vague, they will have to show that their convictions and sentences involve a “plain error.”

In some respects, this showing will be easy to make: Where section 16(b) is incorporated into federal statutes, it often defines a criminal offense, or alters prisoners’ statutory maximum and minimum sentences. That is, section 16(b) can automatically result in a prisoner receiving more time in prison, which means a mistaken (or invalid) application of section 16(b) affects prisoners’ substantial rights. In this piece, I flagged the many courts of appeals cases recognizing that additional prison time affects defendants’ substantial rights.

But in other respects, and in other cases, prisoners may have some difficulty in convincing courts that there has been a plain error. Section 16(b) provides one definition of a crime of violence, but statutes often include several definitions of that phrase. Imagine (hypothetically) that a statute provides one penalty (ten years) for prisoners with no prior criminal history, and another penalty (fifteen years) for prisoners with prior convictions for crimes of violence. After Dimaya, prisoners could still receive the higher, enhanced penalty provided that their prior convictions qualify as crimes of violence under a definition other than the one supplied by section 16(b). Sometimes, it won’t be clear which “crime of violence” definition a district court relied on when sentencing a prisoner. Other times, it won’t be clear if a prisoner’s prior convictions qualify as a crime of violence under other provisions defining that phrase. Where those ambiguities exist, some courts of appeals have held defendants who may have been sentenced under invalid provisions can’t establish “plain error.”

Group 2: Federal Prisoners Whose Convictions Have Become Final

For federal prisoners whose convictions have become final, they will encounter a different set of procedural obstacles to remedying their convictions and sentences. Section 2255 provides the remedy to correct flawed federal convictions and sentences. Here, I’ll just flag three procedural obstacles that prisoners attempting to file section 2255 motions will face.

Statute of Limitations. Section 2255 provides federal prisoners with a one-year period to challenge their convictions or sentences. The one-year period generally runs from the date that a prisoner’s conviction becomes final. But the period restarts on “the date on which the right asserted was initially recognized by the Supreme Court, if that right has been newly recognized by the Supreme Court and made retroactively applicable to cases on collateral review.” For prisoners who were convicted or sentenced under provisions that explicitly incorporate section 16(b), Dimaya gives them a one-year window (starting from April 17, 2018) to challenge their convictions and sentences.

But what about prisoners who were convicted or sentenced under provisions that closely resemble section 16(b)? It’s not clear whether the statute of limitations has restarted for them. Here’s an example. Section 16(b) defines a crime of violence as “any other offense that is a felony and that, by its nature, involves a substantial risk that physical force against the person or property of another may be used in the course of committing the offense.” Section 924(c)(3)(B), on the other hand, defines crime of violence to mean “an offense that is a felony and … that by its nature, involves a substantial risk that physical force against the person or property of another may be used in the course of committing the offense.”

If those things sound similar, it’s because they are. Assuming a court of appeals thinks that the best reading of Dimaya is that section 924(c)(3)(B) is also unconstitutionally void for vagueness, did Dimaya restart the statute of limitations clock for persons convicted of section 924(c)(3)(B)? On the one hand, we want errors of that kind to be corrected, and corrected quickly, given that prisoners whose convictions may be affected could be serving more time in prison than they should be.

On the other hand, Dimaya didn’t involve section 924(c); it just involved the materially identical section 16(b). In light of that, did the “Supreme Court” itself recognize that section 924(c) is void for vagueness, as the statute of limitations provision requires? Perhaps not. Moreover, if Dimaya restarted the statute of limitations period, it’s possible the one-year window would close before the Supreme Court itself ever frontally addresses a case involving the constitutionality of section 924(c). That would be a strange result: The statute of limitations to challenge the constitutionality of section 924(c) would expire before the Supreme Court ever addressed the question. In part for this reason, some courts of appeals held that Dimaya’s predecessor decision, Johnson, did not start the statute of limitations period to challenge the constitutionality of the Guideline provision that was worded the exact same way as the provision that Johnson invalidated. If Johnson had started the statute of limitations, these courts reasoned, the statute of limitations would likely expire before the Supreme Court could weigh in.

Retroactivity. Prisoners cannot raise “new” rules of constitutional procedure after their convictions have become final. That rule (the retroactivity bar) would preclude Dimaya claims but for the fact that prisoners can raise “new” rules that are “substantive.” In Welch v. United States, the Supreme Court held that the rule announced in Johnson was substantive and therefore retroactive. The rule was substantive, the Court explained, because it invalidated a provision under which criminal defendants were sentenced. That provision, the Court continued, altered defendants’ statutory minimum sentences and maximum sentences, and exposed them to additional terms in prison. A rule invalidating section 924(c)(3)(B) shares those same features, and therefore would be substantive and retroactive. Most criminal statutes that incorporate section 16(b) either define new crimes, or alter defendants’ statutory minimum and maximum sentences, and therefore affect the term in prison the statutes provide for their offenses. In those cases, a rule invalidating section 16(b) would also be substantive and retroactive.

Procedural Default. Prisoners cannot generally raise claims in section 2255 proceedings if they could have, but did not, previously raise those claims, including in their direct appeals. But that rule (known as the procedural default doctrine) also has exceptions. Two of them are potentially relevant here. The first exception is for “novelty”: If a claim was so novel that a defendant’s counsel could not have anticipated it, then a defendant won’t be barred from raising the claim later on. In most cases, the exception for “novel” claims doesn’t do defendants much good, because if a claim is so novel that the defendant’s attorney couldn’t have anticipated it, then the retroactivity bar would preclude the defendant from raising it after the defendant’s conviction has become final. But that shouldn’t be a problem for prisoners affected by Dimaya, since the rule that Dimaya announced falls within one of the exceptions to the retroactivity bar.

The second potentially relevant exception is for “miscarriages of justice”: If a defendant can establish there has been a miscarriage of justice, meaning the defendant is actually innocent (here, of the defendant’s offense), then a court will hear the defendant’s procedurally defaulted claim. Although defendants will often claim they are actually innocent because of new evidence, or new facts, defendants can also be actually innocent because of a change in the law. In both cases, the defendant was convicted of or sentenced for something that wasn’t a crime. (I explain this argument in greater detail in a forthcoming Virginia Law Review article, Legal Innocence and Federal Habeas.)

For example, in Bousley v. United States, the Supreme Court held that a defendant who was convicted under a mistaken interpretation of section 924(c) could establish that there has been a miscarriage of justice. Bousley reasoned that if the statute, properly interpreted, didn’t apply to the defendant, then the defendant was actually innocent of the offense and could have the defaulted claim heard on its merits. Bousley, to be sure, involved an error of statutory interpretation, whereas Dimaya involves an error of statutory invalidation: The criminal statute in Bousley was valid, it was just interpreted incorrectly, whereas the criminal statutes affected by Dimaya may have been interpreted correctly but they aren’t valid criminal statutes. (Though the fact that the Court held them vague suggests it’s not possible to interpret them correctly in a significant number of cases.) But that shouldn’t matter for purposes of the miscarriage of justice exception: In both cases, the defendant was convicted or sentenced for something that isn’t a crime, either because the statute was interpreted incorrectly or because it wasn’t valid. For that reason, the government, in the wake of Johnson, conceded that defendants who were sentenced under ACCA’s residual clause were actually innocent. The current administration may not make the same concession, if past practice is any indication. But they’d be wrong, for reasons I explain in the article I referenced above (and will post soon).

Group 3: Federal Prisoners Whose Convictions Have Become Final And Who Have Already Filed One Section 2255 Motion

There will be greater difficulties for federal prisoners whose convictions have become final and who have already filed one section 2255 motion. Everyone’s (least) favorite statute, the Anti-Terrorism and Effective Death Penalty Act, imposes severe restrictions on prisoners’ ability to file multiple section 2255 motions. The one restriction that’s potentially relevant to, and accessible to prisoners affected by Dimaya is for “a new rule of constitutional law, made retroactive to cases on collateral review by the Supreme Court, that was previously unavailable.”

Justice Kagan mentioned the “insanity” and “lunatic practice” that Johnson abandoned. But Johnson also revealed the insanity and lunatic practice that results from section 2255’s restrictions on successive motions. The problem is that in Tyler v. Cain, the Supreme Court said that section 2255’s reference to “ma[king]” rules retroactive refers to “holdings,” rather than dicta. That is, a prisoner has to show that the Supreme Court has held a rule retroactive, not just that the rule is retroactive. Justice O’Connor’s concurrence, the majority, and the dissent also contemplated that the Court could “make” a rule retroactive “through multiple holdings that logically dictate the retroactivity of the new rule.”

Has the Supreme Court “held” the rule in Dimaya retroactive? Well…. the best argument that it has would be that Welch made the materially identical rule in Johnson retroactive. The rule in Johnson, like the rule in Dimaya, invalidated a criminal statute on vagueness grounds; and the rule in Dimaya, like the rule in Johnson, will often affect defendant’s statutory maximum and minimum sentences and the amount of time in prison the defendants can serve. The argument on the other side is that the Court hasn’t applied the rule in Dimaya retroactively; it hasn’t applied the rule in a criminal case (the case in Dimaya involved a deportation, which is a civil matter); and it certainly hasn’t explicitly held section 924(c) unconstitutional.

The problem is that there is a very narrow window for the Court to resolve that issue and allow prisoners in this situation to challenge their sentences via second or successive 2255 motions. As I’ve mentioned, prisoners have just one year from the date the Supreme Court announced a new rule to file a second or successive petition for post-conviction review. Dodd v. United States held that the statute of limitations begins to run “one year from the date on which the right [the prisoner] asserts was initially recognized by this Court,” rather than one year from the date on which the Supreme Court made the right retroactive. So, assuming a court thinks that the Supreme Court hasn’t made Dimaya retroactive, then the Supreme Court would have to make Dimaya retroactive (by applying it in some case on collateral review) within one year of April 17, 2018. That’s unlikely, given how the Court’s calendar works: The Court doesn’t have any cases on its docket for next year that would do so. And any cases it grants at this point would probably be heard in December, at the earliest.

The Court was able to resolve that dilemma for prisoners affected by Johnson. Will it be able to do so for prisoners affected by Dimaya? We’ll find out.

Group 4: Plea Deals

Then there are the group of prisoners who pleaded guilty to crimes that incorporate section 16(b), or are analogous to it. Can these prisoners challenge their convictions and sentences?

Here too, the answer is probably “we’ll find out.” In Class v. United States, the Supreme Court held that a defendant doesn’t waive the right to challenge the constitutionality of the statute she was convicted under merely because the defendant pleaded guilty. So the fact that a defendant has pleaded guilty doesn’t mean the defendant can’t raise a Dimaya claim and attempt to correct the conviction and sentence.

But what if the plea agreement explicitly included a waiver of the right to file an appeal, or the right to challenge the constitutionality of the statute underlying the plea agreement? Here, the law is a little bit more uncertain. Some courts of appeals have established a “miscarriage of justice” exception to appellate waivers and plea agreements that do not allow defendants to waive certain kinds of arguments—that is, they have held defendants cannot waive arguments that would result in a “miscarriage of justice” if a court didn’t hear them. Some of the arguments that defendants cannot waive (in some circuits) include the argument that the statute under which the defendant was convicted is unconstitutional, or any argument that results in the defendant receiving a sentence above the lawful statutory maximum for their offense of conviction. Dimaya claims could fall within those exceptions.

Dimaya spoke of “lesson[s] so hard learned” from Johnson and the ACCA debacle that Johnson corrected. But another lesson that was hard learned from Johnson is that Johnson, or in this case Dimaya, will just be the beginning. Whether those decisions will ultimately benefit the individuals who are currently wrongly incarcerated will depend on what comes next, and specifically on how courts interpret the many draconian restrictions on post-conviction review. 

This article was originally published on Harvard Law Review Blog on April 17, 2018, and is reprinted with permission from the author, with minor edits.

Leah Litman is an assistant professor of law at University of California, Irvine School of Law, where she teaches and writes on federalism and federal post-conviction review.


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