I've watched Sean Combs get acquitted twice. Over 24 years, his recklessness and eye for star lawyers never changed.

Business Insider

04-07-2025

Back in 2001, he was "Puffy."
For two months, Sean "Puffy" Combs strode through a dense press scrum and into his Manhattan guns and bribery trial wearing a different crisp, shiny suit each day.
I remember neckties and matching pocket squares. And one morning, before the judge took the bench, he sat at the defense table, arms outstretched, as defense attorneys Johnnie Cochrane and Ben Brafman sat on either side, affixing his cufflinks.
"If it doesn't make sense, you must find for the defense," the late Cochrane, a dapper dresser best known for his defense of OJ Simpson six years earlier, quipped for reporters.
I covered that state-level case for the New York Post, watching as Combs, then 31, won a full acquittal after his lawyers convinced a jury that he did not fire a bullet from a 9mm semiautomatic Smith & Wesson into the ceiling of a Times Square nightclub.
Jurors also acquitted him of offering his chauffeur $50,000 to take the rap for another gun found under the seat of the Lincoln Navigator he shared with then-girlfriend Jennifer Lopez. Combs had faced up to 15 years in prison in that case.
"This has changed me and matured me," he promised after the happy outcome, saying he had given up nightclubbing in favor of church-going.
On Wednesday, 24 years later, I watched as a senior correspondent for Business Insider as a very different-looking Combs won surprise acquittals on federal racketeering and sex trafficking charges in a federal courthouse barely a block south of where the prior trial was held. A jury found him guilty of lesser Mann Act charges related to transporting his victims for prostitution.
This Combs — now "Diddy" — remains in custody, as he has for the past 10 months. Each day of the trial, he was escorted into the courtroom by federal marshals, wearing jail-approved khakis and a rotation of five thin, blandly colored sweaters over white collared shirts.
His hair is mostly gray now, deprived by his jailers of the "Just For Men" brand dye that one of his personal assistants testified he kept in his toiletry bag.
A quarter century ago, Sean "Puffy" Combs exuded swagger in court — even something approaching menace. "I'm a human being," I remember him saying as he glowered at me in the hallway once, unhappy about his coverage.
But Sean "Diddy" Combs could be Puffy's pleasant uncle, passing out Post-it notes full of advice and encouragement from his seat at the defense table like so many half-wrapped Jolly Roger candies.
"GREAT JOB!!!" read a note I once saw him hand lead attorney Marc Agnifilo.
Each morning and again at day's end, Diddy greeted most of his nine lawyers with hugs and fist bumps.
Puffy, circa 2001, was too aloof to be a hugger of attorneys — not until the verdict, when Combs, Brafman, and Cochran leaned in for a euphoric, seated embrace.
But there are throughlines linking then and now.
For both trials, an international press corps was drawn, moth-to-flame, by the certainty of a celebrity defendant and the hope that a still-bigger celebrity might steal the show.
J-Lo had been briefly in custody soon after the nightclub shooting, after a stolen gun was found inside her and Combs' chauffeured car. She was not charged, and while she testified at Combs' grand jury, neither side called her as a trial witness.
This time around, Kanye, too, disappointed; his cameo appearance at Combs' courthouse last month was over in a blink, 30 minutes tops. He was turned away from the courtroom by federal marshals, and Combs, like many in the press, didn't even see him.
Combs' recklessness is another parallel.
His lawyers acknowledged in closing arguments last week that Combs used drugs and committed domestic violence.
Federal agents testified at trial that they seized three AR-15 rifles with defaced serial numbers when search warrants were executed at Combs' homes in March, 2024, at a time when prosecutors allege he knew he was under investigation.
Combs was not charged for the weapons, and maintained through his lawyer that the guns belonged to his security guards.
"His brazenness is unmatched," lead prosecutor Maurene Comey told US District Judge Arun Subramanian during successful arguments against bail on Wednesday.
"He's an extremely violent man with an extraordinarily dangerous temper, who has shown no remorse and no regret for his violence toward multiple victims," she said.
There was reckless behavior the last time Combs was arrested, too. An evening of clubbing with a gun-toting entourage nearly cost Combs his freedom and burgeoning career as a multimillionaire music and lifestyle entrepreneur.
New York Supreme Court Justice Charles Solomon sentenced Combs codefendant Jamal "Shyne" Barrow to 10 years in state prison. (Barrow, then 21, had the unfortunate timing of running out of the club and into the arms of two arriving cops, a recently-fired gun still warm in his waistband.)
Solomon told me Thursday that he would have sentenced Combs to three and a half years in prison and remanded him on the spot, had he been convicted of gun possession for the firearm police recovered under the front seat of the Navigator.
Combs could have received more time, the now-retired judge said, given that the car had fled up Eighth Avenue with Combs and J-Lo in the back seat and the NYPD in pursuit.
"Another gun came flying out the car from the back seat" during the chase, Solomon recalled.
Another through-line — good lawyering.
"He had Ben, one of the best criminal defense lawyers in the city, and of course Johnnie Cochrane," Solomon said of the 2001 trial.
"And it worked. They certainly had enough to find him guilty," Solomon said.
"That weapon in the car — there was a presumption of possession," Solomon said. "Maybe it was jury nullification, who knows."
"He's a lot of things to a lot of different people. He's probably helped a lot of people make a lot of very good music, helped a lot of careers, started a lot of businesses," he added.
Combs' acquittal on sex trafficking and racketeering means he no longer faces a potential life sentence. He faces anywhere from zero jail time to as much as 20 years in federal prison for the two counts he was convicted of on Wednesday: transporting two ex-girlfriends across state lines to engage in sex acts with male escorts — the so-called "freak offs" at the heart of the trial.
"It's a partial win. He didn't win this case. He still faces considerable time," Solomon said.
"Oh my god I certainly would," he said when asked if he'd give Combs' prison time if he were once again Combs' judge.
"I would give him a lot of time," he added. "Because of what he did in the past, obviously, his background, and the violence involved here now. A leopard doesn't change his spots."