Diddy do it? You’ll have to be more specific. He’s facing quite a bit of legal jeopardy.
Diddy get a bum rap? That remains to be seen.
Diddy really have over 1,000 bottles of lube in his house? Yeah.
Diddy kill his career? Most likely, yeah.
Whenever anyone asks me who’s the most famous person I’ve ever met, my answer is always the same: Diddy.
Technically he was still Puff Daddy at the time, although if we’re being really specific, he was Sean Combs — as in The People of the State of New York v. Sean Combs.
I met him as he was being prosecuted by the Manhattan District Attorney for a 1999 nightclub shooting. Combs, who was there with his then-girlfriend, Jennifer Lopez, was indicted alongside his bodyguard, Anthony “Wolf” Jones and his then-protege, Shyne — a young rapper from Belize who sounded uncannily like The Notorious B.I.G. Lopez was never charged and broke up with Diddy during the trial, eventually hooking up with Ben Affleck for the first (but not the last) time.
At the time, Combs was riding high as the head of Bad Boy Records — a producer extraordinaire who had recently branched out to rapping and performing as a solo artist. He had survived the destructive East/West Hip Hop War and with his rivals at Death Row Records in disarray, Combs looked poised to dominate hip hop for the next few years.
And that’s what happened. His use of upbeat tempos and obvious samples from hugely popular songs gave his singles and albums a party-like atmosphere — something that was reinforced with his big budget music videos, which often featured people in brightly colored outfits drinking and dancing at a club or bar. After the twin shocks of the 2Pac and Biggie murders, Diddy’s brand of feel-good hip hop proved to be just what the doctor ordered, and the next few years featured many rappers attempting to co-opt Puffy’s style in much the same way that many had tried to copy Dr. Dre earlier.
I was working as a paralegal for the D.A. at the time of his criminal trial and randomly ended up in an elevator with Combs one morning as we were both heading to court — me to deliver some files, him to meet with his counsel, Johnnie Cochran and Ben Brafman. There are two things I remember about the future Diddy. One, he was taller than I thought he would be (I don’t know why I thought he was short — maybe all those videos of him with Biggie together warped my view of him). Two, his suit looked like it cost more than my entire wardrobe — actually, I’m sure it did. (Also, as we made our way from the elevators to the courtroom, I was slightly ahead of him. When we turned the corner, Cochran had his back to us and must have been informed that his client was coming up. So he turned around to offer a hug, only to frown once he realized it was me and not his client. It was probably the complete opposite of the euphoria he must have felt that day in court when O.J. tried on the bloody glove.)
And, of course, the other thing I remember was that he was acquitted. Despite a couple of witnesses testifying that they saw Diddy shooting a gun inside the club, the jury believed the Bad Boy impressario’s claim that he was unarmed that night. His bodyguard was acquitted, too.
Shyne, however, was convicted and served time in prison before being deported. In 2024, one of the shooting victims recanted her testimony pointing the finger at Shyne and accused Diddy of firing the shot that hit her. She also accused Diddy of coercing her and providing financial incentives for her to testify the way she did. Furthermore, a 2024 documentary on Shyne accused his lawyers of selling him out and sacrificing him for Diddy.
All of that just underscored how powerful he was at the time. And in the years since, he became even more bulletproof. It’s not hyperbole to say that Diddy rose like a phoenix from the ashes of his criminal trial and reached even greater heights of fame, becoming an actor (he was hilarious in Get Him To The Greek playing [checks notes] an unscrupulous record company executive), fashion mogul, reality TV show host, and entrepreneur.
His music career also flourished over the next decade or so before slowing down thanks to changing industry norms and musical tastes, as well as his own outside ventures. His 2003 single “Shake Ya Tailfeather” from Bad Boys 2 went to #1 on the Billboard charts and his 2002 remix album, We Invented the Remix, went platinum. In 2004, he performed at the infamous halftime show for Super Bowl XXXVIII and hosted the 2005 MTV Video Music Awards. His 2006 album, Press Play, went gold and produced several hits, while his 2010 album, Last Train to Paris, gave him his last big hit single to date, the double platinum selling “Coming Home.” He also did a well-received Bad Boy Family Reunion Tour in 2016 with several of his acts including Ma$e, Faith Evans, Lil’ Kim, 112 and others. Shyne, who has more or less left the music industry, even made an appearance — albeit live via satellite from Belize.
He also continued to produce albums and songs for top artists, including Mary J. Blige, Jay-Z, Britney Spears, Ice Cube, Kayne West and others — although that has also slowed down in recent years.
Most importantly, Diddy did a great job at smoothing over his rough edges, at least in public. He turned on his charm and charisma, making him seem likable, marketable and, most importantly of all, safe. He wasn’t as humorous or effortlessly funny as Snoop Dogg, but like his former rival, Diddy had seemingly survived a serious criminal charge and come out of it looking reformed and more respectable.
Of course, that’s what most of us saw. Others saw differently.
In the years since his acquittal, he continued to rack up a laundry list of assault allegations and complaints — albeit nothing serious enough to derail his career. He escaped some other legal entanglements without any long-term harm, including complaints about worker conditions at his Sean Jean clothing factories and, most sensationally, accusations of being involved in planning the 1996 murder of rival 2Pac (allegations that the L.A. Times later retracted).
Meanwhile, there were lots of rumors about some pretty salacious and deviant things in his private life — as well as hints that he was not a very nice person, especially when the cameras were off. Despite the seriousness of some of these allegations, for many years they stayed at the level of rumor and gossip as Diddy faced no legal consequences. Maybe instead of Puffy, Puff Daddy or P. Diddy, he should have been nicknamed “Teflon Sean.”
His luck seems to have run out.
In 2017, his former chef filed a lawsuit against him for sexual harassment. The lawsuit was settled for an undisclosed amount two years later and things seemed to quiet down for a while.
But then in 2023, Combs was hit with a lawsuit from Cassie Ventura, a former girlfriend and protege. The “Me & U” singer was in a long-term relationship with Combs from 2007 to 2018 and accused him of rape, sexual abuse, assault and sex trafficking, among other crimes. These lawsuits can take a long time to settle, but Diddy moved faster than a lightning bolt and made a deal with Ventura the day after she filed. Maybe they had already been negotiating and she filed the suit to give herself some leverage and maybe even force his hand?
Or maybe Combs knew there could be more lawsuits coming and hoped to stem the tide by settling the Ventura suit immediately and getting it out of the news cycle. If that was the case, then his efforts were for naught, as the floodgates opened and many accusers stepped forward to file sexual misconduct lawsuits against him. The week after he settled his Ventura suit, a woman accused Combs and singer Aaron Hall of Guy of sexually assaulting her when she was only 16 years old. Another woman alleged that Combs drugged and raped her and recorded it on video. One woman claimed she had been gang-raped at a Bad Boy studio when she was still a teenager and another claimed she was raped and impregnated by Combs and then pressured to have an abortion.
Meanwhile, in September 2024, Dawn Richard, a cast member on Diddy’s Making the Band reality show on MTV and member of Diddy’s girl group Danity Kane, filed a sex trafficking, sexual assault and harassment lawsuit while backing up Ventura’s claim of abuse and assault at Combs’ hands. Another lawsuit accused Combs and Jay-Z of raping a then-13 year-old girl at an MTV Video Music Awards afterparty in 2000. The lawsuit was dismissed after the accuser decided not to go forward (Jay-Z issued a statement calling the allegations “frivolous, fictitious and appalling” and has, since, filed a defamation lawsuit against the accuser).
And that’s just a sample of the legal jeopardy Combs is in. According to an October 1, 2024 story in The Washington Post, Combs could be facing hundreds more sexual misconduct lawsuits.
Then there’s the big one — the most serious legal issue he faces and the one that could land him in prison for the rest of his life.
On March 25, 2024, federal agents raided Combs’ properties in New York, Miami and Los Angeles, recovering some electronic equipment, lots of drugs, some modified AR-15s and, in the bit that got the most attention, over 1,000 bottles of baby oil and lube.
That last item became relevant after reports emerged of Diddy holding debauched parties featuring live sex acts, drug use and other things that would make Caligula or Mötley Crüe blush. Many A-Listers who had allegedly attended these “freak-offs” faced scrutiny for their ties to the now-disgraced mogul, including Leonardo DiCaprio, Mariah Carey, Justin Bieber, Jay-Z and Beyoncé, and others.
Diddy was not immediately arrested after the raid, but the damage to his image was done. After all, the feds almost never take a step like that unless they already have a mountain of evidence against someone. That, plus all of the sexual misconduct lawsuits already filed against Diddy changed the narrative around him.
Then in May 2024, Diddy’s image took a bigger hit when CNN released surveillance footage of him striking Ventura in a hotel lobby from 2016. The footage was so damning that Diddy didn’t even try the Shaggy defense (as in “It Wasn’t Me” — it worked for R. Kelly during his first sexual assault trial back in 2007) and immediately released a statement expressing regret for his “inexcusable” actions.
Finally, in September 2024, Combs was arrested by the feds and indicted on sex trafficking and racketeering charges. He pleaded not guilty and faces up to life in prison. His trial is scheduled to begin in May 2025.
This is where I put the standard disclaimer that allegations listed in an indictment are accusations and are not proof of guilt. Diddy is entitled to the standard presumption of innocence that we give all criminal defendants in this country. Plus, anything can happen in a trial and Diddy can afford good lawyers, so you never know (although one just loudly quit his defense team).
So with all of that being said, I don’t think it’s premature to predict that his career is done and that he’s most likely heading to prison and bankruptcy.
For one thing, the feds don’t bring charges on a long-term investigation like this unless they have a rock-solid case. There’s a reason why they win over 90% of the time and only 2% of defendants even bother to go to trial against them. On a long term investigation like this, you can bet they have years and years of evidence against Diddy.
Additionally, the fact that he was denied bail says a lot. It’s rare for non-capital defendants to get denied bail, and the stated reason was that the court was concerned about his history of violence, as well as allegations of potential witness tampering. That means he’s being treated more as a mob boss and not a celebrity, which raises the stakes considerably. Judges also consider the strength of the charges against a defendant in deciding whether or not to set bail. Evidently, this judge thinks the prosecution has a pretty strong case.
Secondly, trials are about storytelling, and the better story (or at least the one that sticks with the jury) usually wins. If there’s a piece of evidence that really resonates with the jury, then even better. When the feds recovered those gold bars from Senator Bob Menendez, I knew his goose was cooked. Not only is that the kind of detail people remember but it really illustrates the depth of the corruption he was accused of.
The 1,000-plus bottles of lube might not be a smoking gun the way those gold bars were for Menendez, but it does reinforce the government’s case against Diddy. After all, prosecutors will have to prove beyond a reasonable doubt that Diddy abused all of these women sexually and coerced them into performing various sex acts — including at his “freak-offs.”
There’s really no reason why anyone would have that much lube unless it was in furtherance of those alleged sexual acts. I doubt even the Board of Directors at K-Y has anything approaching that amount in their homes.
As such, that’s the kind of detail that will stay with you. Heck, look at all of the jokes that have already been made about Diddy having all of that lube.
Of course, I could be completely wrong and he could beat all of the lawsuits and criminal charges and emerge even stronger. I guess there’s a possibility that this whole thing could be a conspiracy between all of these accusers and the federal government (R. Kelly tried to make a similar argument — and it didn’t go well for him). And with the ongoing turmoil in the D.O.J., as well as Diddy’s one-time friendship with the current President, a pre-trial pardon certainly can’t be ruled out.
But even if that were to happen, it wouldn’t shield him from the sheer volume of civil lawsuits against him that will inevitably drain his resources further. Let’s assume, for argument’s sake, that he and his lawyers are able to get most of them dismissed. Most likely there will still be some lawsuits that survive, and if he settles those suits, it will cost him plenty of money (to say nothing of his legal fees).
That’s no big deal as long as money is coming in — it’s all about the Benjamins, right? Unfortunately for him, he’s radioactive right now, which means he’ll be lucky if he gets a few Hamiltons or Lincolns. Businesses have cut ties with him and his clothing company. He can’t really fall back on his music career since he hasn’t been a reliable hit maker for a while now. He won’t be making any movies, hosting any award shows or doing any high profile performances anytime soon, either. So it’s hard to see how he’s going to avoid losing much or even all of his net worth.
I guess he’ll really find out if the inverse of “Mo’ Money, Mo’ Problems” (less money, fewer problems) is true.
