Headed for sentencing, Sean ‘Diddy' Combs' lawyers aim to show he's no longer a ‘Bad Boy for life'

CNN

a day ago

There was a time when summer for Sean 'Diddy' Combs meant throwing lavish parties and getting captured in paparazzi photos on yachts. This summer, the only images the public saw of him were courtroom sketches.
The man whose rise from intern to mogul looked like a hip-hop fairytale has been on trial for charges related to some nightmarish allegations with salacious details about his private life discussed in detail during the proceedings.
Combs was acquitted of the more serious charges of which he was accused – racketeering conspiracy and sex trafficking. He was found guilty of two counts of transportation to engage in prostitution. Next, comes sentencing with a hearing set for July 8 to discuss a request to expedite that process. For now, Combs remains in custody. He faces up to 10 years in prison for each count on which he was found guilty, although legal analysts predict he will get much less. (He also still faces dozens of civil lawsuits, for which he has denied all wrongdoing.)
After Combs was denied bail ahead of sentencing on Wednesday, his attorney Marc Agnifilo, acknowledging that he didn't see 'a glimmer of light coming from the Court' that the judge would reverse his decision, tried one more time.
In explaining why he denied bail, the judge cited instances of 'violence and illegal conduct' discussed during the trial, including a June 2024 incident between Combs and a former girlfriend who testified under the pseudonym 'Jane.' Agnifilo returned to a point that had previously been discussed in a sidebar during Jane's testimony – that Combs made an effort to get himself into 'a batterer's program.'
'He has these flaws in his personality, which are significant, and which have held him back, which have brought him into this courtroom,' Agnifilo said. 'He is a man who's in the process of working on himself.'
Names and labels can be tricky. In closing arguments, Assistant US Attorney Maureen Comey had to rather amusingly remind the jury that when she referenced 'enterprise' while speaking, she was referring to the alleged criminal enterprise for which Combs was ultimately acquitted of running, not his company, which is called Combs Enterprises. Ahead of his sentencing, Combs' attorneys are up against a label and an image nearly 25 years in the making – one in which Combs declared himself to be a 'bad boy for life.'
In 2001, Diddy released the song 'Bad Boy For Life,' featuring fellow rappers Black Rob and Mark Curry, in which he rapped, 'Don't think, 'cause I'm iced out, Imma cool off.' Bad Boy was also the name of the record label he founded in 1993.
'Bad Boy was kind of modeled after (record label) Death Row because Death Row had become a movement. We wanted to model ourselves behind the record companies that were movements, like Motown, Def-Jam, Death Row,' Combs told Rolling Stone in 1997. 'These were record companies that were the sound of the culture, and we wanted to become another sound of the culture.'
The 'bad boy' culture Combs cultivated, according to prosecutors, was one of excess and bursts of violence.
'He's an extremely violent man with an extraordinarily dangerous temper who has shown no remorse and no regret for his multiple victims,' prosecutor Maurene Comey said after Combs was denied bail following the verdict.
As Combs awaits sentencing, his attorneys are telling a different story.
'I think that if the trial showcases one thing, he's done remarkable things in his life,' Agnifilo said. 'He came here, he faced the court, he's been decent with the court each and every day, and he just deserves the chance.'
Following the reading of his split verdict, Combs dropped to his knees and appeared to be in prayer. Such a display was not entirely surprising from a man who in the past has shared his thoughts about contradictions between public personas and private conduct.
Here's some of what he has said:
The federal criminal case was preceded by a civil suit from Combs' former girlfriend, singer Cassie Ventura, who made disturbing abuse allegations against Combs. He denied the allegations and the suit was settled within one day. Combs later posted an apology video after CNN last year exclusively aired footage of him physically attacking Ventura in 2016.
During a 2015 interview on the syndicated radio show 'The Breakfast Club,' Combs reflected on his romantic relationships.
'I could promise you that… If I'm in a relationship with you, like 25 percent of your time you're gon' feel like, 'Oh man, I hate being here, oh man I hate this guy. Oh man, he cheated on me, he lied on me!'' Combs said.
'That's 25 percent, know what I'm saying? But then there's 75 percent of, 'Imma make you the happiest woman in the whole wide world,'' he continued. 'I'm going to be there to support your dreams, I'm going to be there to hold you, listen to you. I'm going to be there to be your best friend and I promise you'll smile the most. You know who I am, this is what it is: 25 percent, 75 percent, which deal would you choose?'
Combs was asked by Ellen DeGeneres during her daytime talk show in 2009 about loaning his Miami home to Chris Brown and Rihanna for a reunion after Brown was accused of brutally beating Rihanna over Grammys weekend earlier that year.
DeGeneres expressed surprise as to why Combs would aid Brown in light of the allegation, and the mogul said, 'I'm the type of person who doesn't cast judgment on somebody.'
'If friends ask me for a favor, then I'm gonna be there for a favor,' Combs said. 'As long as I know the energy of the favor is positive.'
He appeared less than comfortable with the conversation even as he told DeGeneres he 'doesn't feel it's right for anybody to hit anybody at the end of the day.'
'People who've been in relationships, we know sometimes these relationships get ugly and sometimes it doesn't come out into the forefront the way this one has come out,' Combs said at the time. 'It's a lot of stones being thrown and we don't know exactly what's going on.'
Brown and Rihanna ultimately split, and in June 2009 he pleaded guilty to assaulting her.
Fuse's 'On the Record' featured an interview in 2012 in which Combs discussed topics ranging from his career to his late father.
A portion of the conversation centered on his Sean John fashion line.
The interviewer, journalist Touré, asked Combs about his style advice for men.
That led Combs to discussing being a proponent of 'the love movement,' and offering men 'anti-ashiness' grooming advice which stressed the importance of using lotion to battle dry, ashy skin.
His trial included photo evidence and lengthy discussion regarding large amounts of baby oil procured for the sexual encounters Combs participated in called 'Freak Offs' or 'hotel nights.'
His 'love movement' was not just a one-off. Combs legally changed his middle name to 'Love' in 2021. He named his youngest child Love after she was born the following year.
His name change came after the 2018 death of Kim Porter at the age of 47 from pneumonia with whom Combs shared twin daughters D'Lila and Jessie, 18, son Christian, 27, and her son Quincy Brown, 34, whom Combs helped raise.
'Whenever I was around her, I felt as though God had his hand in it. I always felt like God had sent her,' Combs told Essence in an interview with Dream Hampton after Porter's death. 'Nobody could love me the way she loved me, especially as, you know, as crazy as I acted. I mean, she loved me through some real s**t.'
When Combs was presented with a lifetime achievement recognition at the BET Awards in 2022, he again talked about faith and love.
'Anything I do is through God,' Combs said. 'Anything I do is through love. That's what I evolve to be. And that's what I'm doing right now.'
Ventura was among the people he referenced.
'I'mma keep it a hundred with y'all, I was in a dark place for a few years,' Combs said, before thanking 'Cassie for holding me down in the dark times. Love.'
'I'm afraid with Puff [Combs] walking from the most serious charges that he's, not only him, the whole entire discourse, I just wonder what we're going to learn from this,' Hampton told CNN after the verdict this week.
Whether the man who has gone by many names can truly change is yet uncertain. Regardless of the professional or personal accomplishments touted by his attorneys, Combs is now also a convicted felon.
His 'bad boy for life' legacy seemingly solidified.