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 federal sentencing 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, Joseph was sentenced to one year and one day. He served 124 days in federal custody before transitioning to home confinement.
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.
Joseph has been retained in more than 500 federal cases.
In one case described in his December 8, 2025 Bloomberg Law article, a client whose plea agreement stated a range of 168 to 210 months received a sentence of one year and one day—more than 94% below the 210-month high end. This compares the sentence imposed with the stated plea range; it does not describe a reduction of an already-imposed sentence. Past results do not predict future outcomes.
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. An American Bar Association member and Criminal Justice magazine contributor, his authored work includes the nine-page Summer 2026 feature and analysis published by the Federal Bar Association. His Law360 Expert Analysis addresses sentencing variance, mental-health mitigation and cryptocurrency conspiracy cases. He serves on Law360’s 2026 Criminal Practice Editorial Advisory Board; the appointment does not imply endorsement of SAG’s services. Business Insider has quoted him, and Us Weekly has featured his interview with five-time Emmy Award-winning investigative journalist Kristin Thorne for “Uncovered.” These media appearances are distinct from his authored publications.
Joseph appeared on the American Bar Association Criminal Justice Section’s JustPod: From Prison to Prison Consultant: Discussion with Joseph De Gregorio. The conversation provides personal and professional background on his transition from imprisonment to consulting. His ABA fireside-chat appearance is recorded separately in the Media archive as a speaking engagement.
Joseph is also a scheduled panelist with Nicholas Kaizer for the American Bar Association webinar Federal Sentencing Reduction: Engineering Drastic Downward Variances in White-Collar Matters, October 19, 2026. View the program and register at the ABA Learning Center →
Beyond his casework, Joseph is involved in academic and reentry-focused initiatives. He is a visiting lecturer in criminology at Montclair State University.
In Conversation with Kristin Thorne
Joseph De Gregorio joins five-time Emmy Award-winning investigative journalist Kristin Thorne in the Us Weekly Uncovered feature Federal Sentencing Strategist Reveals the “Systematic” Reasons Why Some “Real Housewives” Stars Commit Fraud. Watch Joseph share his perspective on white-collar crime, federal sentencing, and the human decisions behind these cases.
Read / watch the Us Weekly feature →
Professional recommendations
“I'd gladly team up with Joe again, and wouldn't hesitate to recommend him to other counsel and their clients.”
Justin Danilewitz
Chair, White Collar and Government Enforcement Practice, Saul Ewing LLP
LinkedIn recommendation · October 13, 2025
“In each case Joseph delivered far above our expectations.”
“We look forward to continuing our work with Joseph and recommend him without reservation.”
Richard Levitt
Partner, Levitt & Kaizer
LinkedIn recommendation · September 3, 2025
Read documented client experiences → · Request a Private Case Review →
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.
Before sentencing, SAG works directly with defendants on mitigation, narrative development, and supporting records, coordinating with defense counsel as appropriate. After sentencing, SAG provides independent practical consulting to individuals and families on prison preparation, documentation, and release planning. Legal advice, legal strategy, and court filings remain with qualified counsel.
Begin Your Strategic Case Review
Every engagement begins with a confidential review of your case, sentencing posture, and objectives to determine whether Sentencing Advocacy Group can provide meaningful strategic value.