The Man with 9 Lives: The Joseph De Gregorio Story

Joseph De Gregorio spent 24 years on Wall Street. He survived a liver transplant with COVID complications that should have killed him. Then, just as he was getting his life back, the Securities Exchange Commission called.

From Brooklyn to Wall Street

Joseph grew up in Bensonhurst, Brooklyn, on 15th Avenue and 71st Street. He went to Catholic school right across from his house and collected baseball cards as a kid. “I saw the similarities when my dad was looking at the Sunday Times, and he was looking at his Con Ed stock, and I was checking my cards next to him, and then he said, you know, look, this is the same thing,” Joseph told me. “You’re looking at, you know, how much you’re done mattingly one up this month, and, you know, I’m looking at, so I always wanted to work in finance.”

By 2000, he’d skipped college entirely and went straight to Wall Street. He was the youngest to get his Series 7 license, passing it in six weeks when most people took six or seven months. He started at U.S. Securities and Futures on 100 Wall Street, the third biggest futures firm at the time, making cold calls from 7 AM to 10:30 PM and earning $600 a day.

The 2008 Crash and the Spiral

Joseph watched the credit and bond markets closely, seeing red flags everywhere in 2007. But he had clients in what seemed like the safest investments. Fannie Mae with its triple-A rating from Moody’s. Bear Stearns. Lehman Brothers, a 158-year-old institution. “If you would, that was going out of business, I wouldn’t have believed you,” he said.

By August 2008, all three had collapsed. His $50 million book got decimated between September 2008 and March 2009. The owner of his firm killed himself. Joseph faced three arbitrations from contingency lawyers who smelled blood in the water. He settled all of them by 2011, paying clients back in full.

That’s when the drinking really started. “It was really disheartening at that point when I settled with all of them. And at that point, I was 35 years old,” Joseph said. What began as going out for dinner with other traders turned into something much darker by 2015.

The Physical Breakdown

By 2016, Joseph’s body was shutting down. He turned yellow. His legs and feet swelled so badly he couldn’t wear dress shoes anymore. Tremendous stomach pains. But he kept showing up to work in a suit, talking to clients all day, functional on the surface.

He moved to a private equity firm that year, working with pre-IPO investments like Palantir at $8, Airbnb, and Lyft. “But I was so past to the point. And I was lying to everyone. I was lying to everyone,” he told me. The lying was about the drinking, but it went deeper than that.

“I started to rationalize a crime in my head,” Joseph said. After Palantir went public and clients sold in the 30s from $8, he created four victims through securities fraud. “I wake up with a pain in my stomach every day that it doesn’t go away. What I did, they’re always in the forefront of my mind.”

A Liver Transplant in the COVID Epicenter

In January 2020, doctors forced Joseph to go to the hospital for blood tests. They wanted him admitted to detox. He refused. Three months later, when COVID protocols meant you couldn’t get into a Manhattan hospital unless it was COVID-related, he was rushed to Columbia Presbyterian.

They put two hoses on each side of his stomach, draining buckets of bile. He was detoxing and barely cognitive. “I got to the point where I drank myself into a coma,” he said.

On July 21, 2020, despite never being on the transplant list, Joseph received a liver transplant. The liver had COVID in it. When he woke up in ICU, they immediately started him on remdesivir and convalescent plasma treatments. His fever hit 106.8 degrees. He went on a ventilator for 10 days, then again for eight more days when his lungs collapsed.

“I remember everyone around me in the ICU was everyone was on ventilators. And all I saw was white sheets being pulled over. And I said, you know, I’m never going to make it out,” Joseph told me. When he finally woke up the second time, there was a priest standing in front of him.

The Call That Changed Everything

By September 2020, Joseph was finally out of the hospital and sober for the first time in years. His pastor, Father Jeff Conway, started bringing him to AA meetings. During one of their sessions reading the Big Book together, Joseph confessed what he’d done.

Two days later, the Securities Exchange Commission called. “They said, is this Joseph DeGregorio? I said, yes. They said, we’d like to speak with you. I said, would it be okay if I give you guys a call back in the next day or two? They said, sure,” he recalled.

Joseph felt relieved. He hired attorney Nicholas Kaiser and told him everything. “I said, Nicholas, this is what I did. This is how I did it. I was the only one involved with my crime… I don’t want to give them the run around. I’ve been waiting for this call.”

Turning Prison Time into Study Time

Joseph approached his federal case like a full-time job. He studied federal judges, particularly Judge Benita Pearson’s advice that defendants should “take their case as a full time job and come into sentencing exhausted.” He worked at Amazon from 6 PM to 6 AM on a forklift, then as a golf ranger for $15 an hour, volunteering in the evenings and taking online certifications until 2 AM.

He started paying restitution nine months before sentencing, sending his lawyer $400-500 monthly to hold in escrow. He brought stacks of cash, gold coins, crypto wallets, watches, and jewelry to his lawyer’s office to turn over to the government.

The guidelines called for 41 to 51 months. On September 14, 2022, Joseph was sentenced to a year and a day. A 75% reduction.

Medical Hell in Federal Prison

Joseph reported to Federal Medical Center Devins on November 17, 2022. Within an hour, they put him in solitary confinement and didn’t give him his anti-rejection medication for three days. He was drinking sink water with no immune system, banging on the thick door trying to get guards’ attention.

“I was banging on the door saying, Hey, listen, I just self surrendered. I had a liver transplant. Please, I just need my immunosuppressants and my anti rejection meds,” he said. One guard told him he should have thought of that before coming there.

After less than a month, abnormal blood tests led to another medical emergency. They rushed him to Beth Israel Deaconess Hospital in Boston for liver rejection, where he spent 17 days chained to a hospital bed with 24-hour guards. His wife had no idea where he was.

When they brought him back to Devins in a blizzard on December 29th, they put him back in solitary for quarantine. Again, no medicine for days. “December 29th, December 30th. New Year’s Eve is when I first got my medicine,” Joseph said.

Joseph served only 25% of his sentence before release. Today, he runs JN Advisors, helping other white-collar federal defendants with the mitigation strategies that cut his own sentence by three-quarters. He uses everything he learned about the federal system to help others navigate what he calls “the process.”

Five years ago, Joseph was on a ventilator in COVID ICU. Today, he’s building a business around the second chance that liver transplant gave him.