As a young prosecutor, John Gleeson was part of a two-lawyer team that prosecuted mob boss John Gotti. That seven-month trial resulted in 1987 in an acquittal, and one of the jurors was later convicted for taking a bribe from John Gotti’s underboss. Five years later Gleeson was the lead prosecutor in the successful prosecution of Gotti, who was convicted of five murders and numerous other crimes and sentenced to life in prison. Gleeson then took the bench, where he witnessed firsthand the impact of mandatory minimum sentencing. In this compelling episode, Judge Gleeson joins host Vince Citro to discuss his journey from prosecutor to federal judge, sharing how his time on the bench transformed his perspective on justice. He recounts the case of Francois Holloway, whose 57-year sentence was reduced through Gleeson’s efforts while on the bench. This experience inspired Gleeson to create the Holloway Project, a pro bono initiative that seeks sentence reductions for inmates serving excessive sentences, focusing on those who have demonstrated personal growth and reform. As of the time of this podcast, the Holloway Project at Debevoise had obtained sentence reductions for 61 clients, and the average reduction is more than 39 years.