Joseph De Gregorio
Founder & President
Sentencing Advocacy Group
Joseph De Gregorio is the Founder and President of Sentencing Advocacy Group, a federal sentencing strategy firm specializing in mitigation, presentence investigation report (PSR) preparation, and post-sentencing execution.
Before founding Sentencing Advocacy Group, Joseph spent over two decades on Wall Street, managing client capital and overseeing trading operations in high-pressure, performance-driven environments. In 2021, he was federally charged in the Eastern District of New York with wire fraud and securities fraud. Facing a guideline range of 41 to 51 months—and without a cooperation agreement—Joseph took an active role in his own defense, directing key aspects of his mitigation strategy, participating extensively in his presentence interview, and working his case continuously through sentencing.
On September 14, 2022, he was sentenced to one year and one day—a reduction of 75% from the guideline range. He ultimately served 125 days in federal custody before transitioning to home confinement, completing roughly 25% of his sentence.
That experience became the foundation for Sentencing Advocacy Group.
Today, Joseph works with federal defendants and defense counsel nationwide, focusing on the phase of a case where outcomes are often most influenced: how a defendant is positioned, documented, and understood prior to sentencing, and how their case is executed after sentencing within the Bureau of Prisons.
He has worked on more than 500+ federal cases, primarily in white-collar matters, including securities fraud, healthcare fraud, tax-related offenses, and complex financial investigations. His clients have included executives, founders, and individuals represented by top-tier law firms across the United States.
Joseph’s work has contributed to substantial sentencing outcomes, including cases involving reductions of 75% to over 90% from guideline ranges. In one case, a client facing a potential sentence of 14 years was ultimately sentenced to one year and one day following a comprehensive mitigation strategy developed from the outset of the case.
His work has also been recognized in federal court. In at least one instance, a federal judge cited a mitigation submission he helped develop as among the most effective the court had reviewed.
Joseph has contributed to high-profile matters, including consulting on the 2025 gambling-related case involving Shohei Ohtani associate Matt Bowyer, where the government sought a significantly higher sentence and the court ultimately imposed a sentence of one year and one day following extensive mitigation efforts.
He is a recurring contributor to Bloomberg Law and Bloomberg Tax, and a contributor to Law360. He serves on Law360’s 2026 Criminal Practice Editorial Advisory Board and has been featured by Business Insider and US Weekly, including analysis for investigative journalist Kristen Thorne’s “Uncovered” series.
Joseph has also appeared as a guest on the American Bar Association Criminal Justice Section’s JustPod, where his work has been discussed in the context of federal sentencing preparation and mitigation strategy.
Beyond his casework, Joseph is involved in academic and reentry-focused initiatives. He has served as a guest lecturer in criminology and maintains advisory roles with organizations focused on reentry, education, and post-incarceration outcomes.
Approach
Joseph’s work is grounded in a simple premise:
Federal sentencing outcomes are not determined solely by legal arguments. They are shaped by how a person is understood—by probation, by the court, and by the institutions that ultimately determine how a sentence is served.
Sentencing Advocacy Group operates in that layer.
The firm works alongside defense counsel to ensure that mitigation, narrative development, and strategic positioning are fully developed, coordinated, and aligned with the desired outcome—both at sentencing and throughout the execution of a sentence.
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