What happens when a Wall Street trader with 24 years of experience faces not just one life-threatening crisis, but nine? Joseph De Gregorio’s story isn’t just about survival; It’s about redemption, second chances, and turning the darkest moments into a mission to help others.
Joseph’s journey began in Brooklyn, New York, where he grew up in Bensonhurst, collecting baseball cards and developing an early fascination with finance. “I was looking at how much my Don Mattingly card went up this month, and my dad was looking at his Con Ed stock,” Joseph recalled. “He said, ‘This is the same thing.'” That simple observation at age 12 would set him on a path that would eventually lead to Wall Street—and to a series of life-threatening crises that would test every fiber of his being.
After getting his Series 7 and Series 63 licenses in 2000, Joseph built a successful career as a Wall Street trader, managing a $50 million book of business. But the 2008 financial crisis changed everything. “I had clients in Fannie Mae, Bear Stearns, Lehman Brothers,” he explained. “If you would have told me that Lehman Brothers, a 158-year-old institution, was going out of business, I wouldn’t have believed you.”
By 2011, after settling three arbitrations and paying restitution in full, Joseph began drinking heavily. “I was really disheartened at that point,” he said. “I started drinking a little more and a little more.” What started as social drinking spiraled into a full-blown addiction that would nearly cost him his life.
By 2016, Joseph’s body was showing the devastating effects of alcoholism. “I started becoming very yellowed. My legs blew up. My feet blew up to the point where I couldn’t wear dress shoes anymore.” Despite these warning signs, he continued drinking, eventually reaching a point where he was “far from sober” and rationalizing criminal behavior.
In June 2020, at the height of the COVID pandemic, Joseph was rushed to Columbia Presbyterian Hospital in Manhattan. “They put two hoses on each side of my stomach when I got there,” he remembered. “It was just draining out buckets of bile.” The doctors told him he needed a liver transplant to survive—and he wasn’t even on the transplant list.
Miraculously, on July 21, 2020, Joseph received a liver transplant. But the liver had COVID, and within hours of waking up in the ICU, he was placed on a ventilator. “I had a 106.8 fever that wasn’t going away,” he said. “I remember everyone around me in the ICU was on ventilators. All I saw was white sheets being pulled over.”
Joseph spent 10 days on the ventilator, then another 8 days when his lungs collapsed again. “They weren’t expecting me to get up from that,” he said. When he finally woke up, there was a priest in front of him, and he was in septic shock. His body initially rejected the liver, requiring intensive treatment to prevent organ failure.
After months of recovery, Joseph was finally discharged in September 2020. But his journey was far from over. “When I got out of the hospital, I get a phone call from the Securities and Exchange Commission wanting to speak with me.” The same crimes he had committed while drinking had finally caught up with him.
Instead of running or making excuses, Joseph chose a different path. “I told my lawyer, ‘Please call them and tell them that I want to fall on the sword. I own what I did. I just don’t want to give them the run around.'” This decision to take full responsibility would become the foundation of his remarkable transformation.
Joseph’s approach to his federal case was nothing short of extraordinary. He began studying federal judges and sentencing guidelines, implementing a comprehensive mitigation strategy that most defendants never consider. “I had a focus on what I had control over,” he explained. “The judge looks at the lawyer as a paid mouthpiece. What am I going to show?”
His mitigation efforts included:
- Paying restitution nine months before sentencing
- Working two jobs (Amazon and a golf course) while awaiting sentencing
- Taking 80+ certifications and courses
- Writing a 4,300-word letter to the judge before his pre-sentence interview
- Creating detailed monthly reports and book reports for his case manager
When sentencing day arrived in September 2022, Joseph faced guidelines of 41-51 months. The judge sentenced him to just 1 year and 1 day—a 75% reduction. Even more remarkable, he served only 25% of that sentence before being released to home confinement.
But Joseph’s story doesn’t end with his release. He immediately began working with Prison Professors and White Collar Advice, consulting with over 300 clients facing federal charges. His results speak for themselves: clients facing 168 months received 1 year and 1 day; others facing 126 months received the same reduced sentence.
“The biggest thing is when people get involved with an investigation, they just think they’re going to hire the best lawyer and that’s it,” Joseph explained. “The real battle is one outside of the courtroom. The prosecutor controls 80% of the courtroom, and you have control over that 20%.”
Today, Joseph is the founder of JN Advisors, a full-service federal sentencing mitigation firm. He’s also completed Columbia University’s Justice Through Code program, joined Defy Ventures’ accelerator program, and serves on the governance committee for the Formerly Incarcerated College Graduate Network.
What makes Joseph’s story so powerful isn’t just his survival—it’s his transformation. “Redemption is a lifelong commitment to me,” he said. “There are two judges: one in the courtroom and the biggest one upstairs.”
His advice for anyone facing federal charges is simple but profound: “You have control over your case. If you think hiring a lawyer and just waiting to go into sentencing, that’s not how it is. You have to really take control over things.”
Joseph’s story is a testament to the power of taking responsibility, seeking help, and never giving up. From a Wall Street trader to a liver transplant survivor to a federal defendant to a mitigation specialist helping others. His journey proves that even our darkest moments can become our greatest opportunities for growth and service.