In this episode, Tom Fox welcomes former Wall Street trader Joseph De Gregorio, who was federally convicted and now applies a “compliance rebuild” methodology to demonstrate genuine remediation under legal scrutiny. This is Part 1 of a two-part podcast series.
Using the Matthew Bowyer illegal sports betting case, Joseph explains the federal pre-sentence interview and pre-sentence report (PSR) process, emphasizing that the probation officer’s credibility assessment and PSR narrative heavily influence sentencing and downstream treatment across the federal system. He describes submitting a 3,500-word personal narrative before the PSR interview, which was attached in full and cited by the judge as mitigation, resulting in a one-year-and-a-day sentence rather than the government’s four-year request. Joseph maps DOJ’s seven corporate compliance program dimensions to individuals via a personal compliance manual, independent accountability structure, credentialed education, verifiable monitoring, documented transparency, voluntary discipline actions, and a post-sentencing continuous improvement plan centered on victims-first accountability.
Key highlights:
Joseph’s Wall Street Past
The Boyer Betting Case
What is a PSR, and why does it drive sentencing
Preparing for the Interview
From Corporations to Individuals
Seven Pillars Framework
Resources:
Joseph De Gregorio – Founder, JN Advisor™ Maximum Sentence Reduction – Minimum Time Served
Initial Consultation: https://forms.gle/2fLczk7bbwM7KSaP6
Bloomberg Law Contributor: “How to Get a Judge to Reduce Your Client’s White-Collar Sentence” – Bloomberg Law
Bloomberg Tax Contributor: Tax Fraud Sentencing Has a Gap Defense Attorneys Are Missing
Featured Expert: American Bar Association
Featured Sentencing Mitigation Expert: Law360
Featured Expert on Us Weekly with 5x Emmy Award Winning Journalist Kristin Thorne for her “Uncovered” Series Click Link For Full Video
https://www.usmagazine.com/crime-news/news/federal-sentencing-strategist-reveals-why-some-real-housewives-stars-commit-fraud/
Tom Fox
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Interested in the intersection of Sherlock Holmes and modern compliance? Check out my latest book, The Game is Afoot in Compliance.
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