Inside Diddy’s Legal Dream Team: The Power Players Shaping His Fate

Quick update on where things stand with Sean 'Diddy' Combs: the court has set a firm release date, the math on his time left is clearer, and his defense army was, frankly, stacked. Here is what that actually means, without the smoke and mirrors.

Where Diddy stands now

Combs was convicted on two counts of transportation for prostitution and sentenced to 50 months in federal prison. He is due out on May 8, 2028. He also owes a $500,000 fine and will be on supervised release for five years once he is out.

Time served at MDC Brooklyn counts toward the sentence, which is why he has roughly 30 months left. In real terms, he is expected to serve about 42 months total — about 85% of the 50-month sentence — with the possibility to earn additional good-conduct time each year under the First Step Act.

For context: when this case kicked off, he was staring down a potential life sentence. After the conviction on the two transportation counts (which carry a maximum of 20 years), prosecutors pushed for 11 years. The defense countered that he had already been punished enough. Relative to the exposure he faced early on, this outcome is very much the result of an aggressive defense strategy landing a narrower sentence.

The defense roster (and why you kept hearing their names)

• Marc Agnifilo – Lead trial counsel and one of the founding partners of Agnifilo Intrater. Agnifilo has tried more than 200 cases over three decades and previously served in the U.S. Attorney's Office for the District of New Jersey and as a Manhattan Assistant District Attorney. His practice is built around high-stakes criminal work — money laundering, racketeering and enterprise corruption, bribery, the works. Past headline clients include NXIVM leader Keith Raniere, 'Pharma Bro' Martin Shkreli, and ex-Goldman Sachs banker Roger Ng. His firm, co-founded with Teny Geragos, pitches itself as representing individuals in complex, sensitive criminal matters. His wife, former prosecutor Karen Friedman Agnifilo, is Of Counsel at the firm.
• Teny Geragos – Co-lead on the Combs case and the other founding partner of Agnifilo Intrater. She handles federal and state criminal matters at the trial and appellate level, and has represented both people accused of sexual misconduct and victims of it. She has also led internal investigations in the construction and healthcare sectors. On the high-profile front, she has been involved with the renewed effort around Erik and Lyle Menendez, whose decades-old parricide case has drawn a wave of public reexamination. If the last name rings a bell: yes, she is the daughter of defense attorney Mark Geragos (clients include Michael Jackson and Chris Brown).
• Alexandra Shapiro – An appellate specialist at Shapiro Arato Bach with more than 30 years in the trenches. She is best known for winning major white-collar appeals, including two Supreme Court decisions that narrowed federal fraud law: Ciminelli v. United States and Percoco v. United States. She is also counsel to Sam Bankman-Fried in his pending appeal.
• Brian Steel – Longtime criminal defense attorney from the Steel Law Firm, recognized recently for representing Young Thug in the sprawling YSL racketeering case. He has been defending clients since 1991, crisscrossing the country and representing everyone from doctors and lawyers to elected officials, judges, athletes, and FBI agents. During sentencing, legal reporter Matthew Russell Lee of Inner City Press (via Yahoo) noted Steel grew emotional while addressing Judge Arun Subramanian:

'I am honored to practice in this majestic courthouse. I sit here with tears in my eyes... Sean has impacted America in such a positive manner... He has taken responsibility.'

• Xavier Donaldson – A veteran New York criminal defense lawyer. Per the New York State Bar Association, he was inspired by his older brother (also an attorney) and focuses on making sure judges understand the 'why' behind a client's conduct before sentencing. He launched his own practice in 2023 after 24 years at the New York firm Donaldson & Chilliest, LLP.
• Anna Estevao – A partner at Harris Trzaskoma LLP who defends individuals and companies in white-collar matters (mail and wire fraud, tax and bank fraud, money laundering, healthcare fraud), as well as cases involving sexual assault and immigration-related offenses. She has been named a Rising Star by Super Lawyers every year since 2021.
• Jason Driscoll – An associate at Shapiro Arato Bach since May 2023 and one of the younger attorneys on the team. Before that, he was a litigation associate at Paul, Weiss, Rifkind, Wharton & Garrison LLP. Recently, his firm touted a win for the former head of HSBC's foreign exchange business in a wire fraud prosecution.
• Linda Moreno – Brought in as a legal consultant to guide jury selection. She is best known for national security and terrorism cases, with clients ranging from actor Wesley Snipes to Guantanamo detainee Mohamedou Salahi. According to her professional bio, she has led the defense in over 100 jury trials and often appears as a legal expert for outlets like the BBC, the New York Times, and Al Jazeera.

A couple notes worth flagging

Yes, Steel is tied to the YSL case — and no, that trial has not lasted 22 years. That claim floating around elsewhere is just wrong.

Bottom line: the outcome is far from nothing — prison time, a hefty fine, and years of supervision — but it is also far less severe than what prosecutors wanted or what was on the table when this all began. However you feel about Combs, his team worked the system exactly how it is designed to be worked.