Justice Notes: Retroacitve Punishment

A White-Collar Journal forum for criminal justice, lived experience, and the personal search for redemption

Attorney and reform advocate Jeff Grant returns to Justice Notes with a timely and provocative analysis of the U.S. Supreme Court’s consideration of Ellingburg v. United States.

Drawing on his extensive work with individuals and families navigating the fallout of white-collar prosecutions, Jeff explores a deeply consequential question: When does restitution stop being restorative — and start becoming punishment?In this week’s Justice Notes, attorney and reform advocate Jeff Grant examines a pivotal Supreme Court case that could reshape how restitution is treated under federal law. Jeff’s perspective comes from decades of working with defendants and families navigating the long shadow of white-collar convictions. His essay explores a crucial question: When does restitution stop being restorative — and start becoming punishment?

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When Restitution Turns Punitive: The Supreme Court, Compounding Interest, and the Limits of Retroactive Punishment

By Jeff Grant, Esq.
Guest Contributor — October 2025

Jeff Grant, Esq. is the founder of GrantLaw, PLLC in New York, providing private general counsel services and working closely with criminal defense lawyers and local counsel throughout the United States. He is also the co-founder of the White Collar Support Group, the world’s first support group devoted to those navigating the white-collar justice system and their families.

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On a brisk October morning this Term, the Supreme Court took up a question with real human consequences: when does a court-ordered restitution obligation — especially one that grows through compounding interest over decades — cross the line from a civil remedy into a criminal punishment?

At stake in Ellingburg v. United States is whether the Constitution’s ban on retroactive increases in punishment — the Ex Post Facto Clause — applies to restitution that expands long after sentencing. During oral arguments, a majority of justices seemed open to the idea that forcing defendants to pay compounding restitution years after conviction is punitive, and therefore constitutionally limited.

If the Court embraces that reasoning, it will profoundly alter how Congress’s restitution statutes interact with victims’ rights and the lingering financial obligations that follow many defendants well beyond their release from prison.

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A Life Sentence of a Different Kind

For me, this issue is not theoretical. I serve as private general counsel to people who have been prosecuted for white-collar crimes and their families, and I’ve seen firsthand how these restitution obligations can become life sentences of a different kind.

Clients who have already served their time, rebuilt their families, and worked to restore their integrity can find themselves facing debts that have quietly doubled or tripled while they were trying to start over.

The Mandatory Victims Restitution Act of 1996 (MVRA) gave courts authority to enforce restitution in many federal criminal cases, often for decades. The law was designed to ensure victims were made whole. But over time, statutory extensions and interest mechanisms have transformed some of these obligations into unending penalties.

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The Case Before the Court

In Ellingburg, the defendant’s restitution grew exponentially because later-enacted laws allowed continued enforcement and interest accrual. What began as a limited, defined obligation ballooned far beyond what was in place when he committed his offense.

The legal question before the Court is simple but profound:
Can Congress or the courts increase a person’s punishment after the fact by changing the financial rules midstream?

The Supreme Court has long tried to distinguish between civil remedies and criminal punishments. Under Kennedy v. Mendoza-Martinez, courts look beyond labels to assess a law’s real-world purpose and effect. During oral argument, several justices pressed the government to explain how a restitution order that compounds for decades could still be viewed as merely “remedial.”

I share that skepticism. In my view, when the government allows restitution to grow through compounding interest long after a person’s release, it ceases to serve a compensatory function and becomes punitive.

There’s an ethical and constitutional equivalence between adding years of interest to a restitution bill and adding years to a prison sentence — both increase punishment after the fact, and both raise serious due process and ex post facto concerns.

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Restoration, Not Retribution

Of course, victims deserve compensation. The moral question isn’t whether victims should be made whole — it’s how to do so within the limits of fairness and constitutional principle. The challenge for the Court and for Congress is to strike a balance that restores victims without condemning defendants to lifelong, unpayable debts.

The practical consequences of this case are enormous. Many people emerging from white-collar prosecutions have already lost their careers, savings, and reputations. Restitution that continues to grow long after sentencing undermines the very idea of rehabilitation. It makes true reintegration nearly impossible.

If the Court rules that compounding restitution is punitive, the decision will likely spark a wave of new litigation as defendants seek relief from ballooning debts. Sentencing courts and defense lawyers will need to be far more precise about the duration and rate of restitution obligations going forward — treating them with the same level of care as the terms of incarceration.

Restitution should be about restoration, not retribution. A fair balance can be struck by allowing victims to recover what was lost while limiting retroactive expansions that transform repayment into punishment. The law must draw a clear line between remedy and penalty, between accountability and perpetual bondage.

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The Stakes for Justice

The Supreme Court’s decision in Ellingburg will determine not only how we interpret the Ex Post Facto Clause, but also what kind of justice system we want to be.

Do we believe that people who have served their time deserve the chance to rebuild — or do we continue to punish them indefinitely through debts that never stop growing?

Whatever the Court decides, one truth remains: the line between remedy and punishment isn’t abstract. It’s drawn across real lives. And for many of my clients — and thousands like them — that line is the difference between freedom and a future still shackled to the past.

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Editor’s Closing Note

Jeff Grant’s essay reminds us that legal reform isn’t only about statutes or precedent — it’s about people and the chance to start again. As the Court weighs Ellingburg v. United States, the outcome will resonate far beyond the courtroom, defining how America measures justice, restitution, and redemption.

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— John DiMenna, White Collar JournalGuest Essay: Part of the White Collar Journal’s “Justice Notes” series exploring the intersection of law, reform, and redemption.

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If you’re drawn to the idea of storytelling as self-reckoning, I’d love to hear your thoughts in the comments.

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