In an unexpected twist of legal fates, hip-hop mogul Sean “Diddy” Combs and fallen cryptocurrency wunderkind Sam Bankman-Fried find themselves sharing more than just a jail cell—they’re also using the same lawyer.
Combs is an inmate at the Metropolitan Detention Center, having pleaded not guilty to charges of sex trafficking, racketeering conspiracy, and transportation to engage in prostitution last month.
Prosecutors allege that for years Combs “used the business empire he controlled to sexually abuse and exploit women, as well as to commit other acts of violence and obstruction of justice.”
A judge denied his request to be released on bond, placing the disgraced celebrity in the same shared prison dormitory as Bankman-Fried—an inmate of the Brooklyn institute since August 2023.
Bankman-Fried, who has vowed to continue fighting for his freedom despite being found guilty of defrauding investors out of billions of dollars, counts Alexandra Shapiro among his legal team.
Bloomberg reported at the time that in April 2024, Shapiro put Bankman-Fried’s sentence and committal up for appeal to the courts.
Six months later and Shapiro—partner at Shapiro Arato Bach—is now seemingly carrying out similar tasks for Combs.
On Monday courts received a notice from Combs’s legal team appealing the federal judge’s decision to place Combs in custody, filed by both Shapiro and fellow attorney Anthony Ricco, per CNN.
Shapiro’s CV
Shapiro working for both Bankman-Fried and Combs may not necessarily involve the pair discussing their respective cases in custody.
Shapiro’s specialty is appeals—a skill both individuals are in need of.
The attorney is described as “one of the nation’s leading appellate lawyers,” who worked her way up from serving as one of Justice Ruth Bader Ginsburg’s first clerks on the Supreme Court more than 30 years ago.
Shapiro, who founded her law firm in 2009, has led successful suits spanning the Supreme Court and the Second Circuit, often representing high-profile white-collar professionals.
Under her representation, charges were dropped against a former Deutsche Bank broker accused of conspiring to commit tax fraud, and reversed for two EY partners accused of helping rich clients evade taxes.
Indeed, Shapiro’s experiences working in white-collar cases led her to write a novel about the subject, Presumed Guilty.
Shapiro did not respond to Fortune‘s request for comment asking when she was first instructed by Combs.
She did not respond to questions about how closely Combs and Bankman-Fried were living.
Fortune approached further representatives for Combs for comment but did not receive a reply.
Diddy dropped
While Combs has vehemently denied the barrage of charges against him, businesses have distanced themselves from the musician and entrepreneur.
The current alleged offenses are the latest in a timeline of charges against the rapper, whose business dealings have included partnerships with alcohol brands and the launch of his own e-commerce platform.
A brand deal with Diageo North America turned sour last year, with both parties concluding their relationship in court.
Combs accused Diageo of racism in neglecting his liquor brands, while the business maintained Combs was responsible for their demise after allegedly putting only $1,000 into the joint venture while the company invested $100 million.
Last year Combs was accused in a lawsuit of subjecting R&B singer Cassie to a yearslong relationship that included beatings and rape—allegations the rapper “vehemently denies.”
Organizations were quick to cut ties.
Fitness brand Peloton, for example, announced in May it “has paused the use of Sean Combs’ music, as well as removed the Bad Boy Entertainment Artist Series, on our platform.
This means our Instructors are no longer using his music in any newly produced classes.”
Likewise Howard University axed its relationship with Combs after a video appearing to show the rapper attacking Cassie in 2016 was released online.
In June, the institution rescinded an honorary degree awarded to him and disbanded a scholarship program in his name.
“Mr. Combs’ behavior as captured in a recently released video is so fundamentally incompatible with Howard University’s core values and beliefs that he is deemed no longer worthy to hold the institution’s highest honor,” a statement from the university’s Board of Trustees said.
