
Cheyenne Roundtree
6
APPEARANCES
5
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012
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Oct 14, 2026
Cheyenne Roundtree - "Bad Boy for Life: The Rise and Fall of Sean Combs"
7:56
9:14

Doireann GarrihyHOST
How did that happen? And would he potentially still be free if he had accepted that?
C
8:03Cheyenne RoundtreeGUEST
So in 2024, I believe, since I have my dates right, or sorry, in 2023, actually, Cassie entered a rehab program.
C
8:12Cheyenne RoundtreeGUEST
She was triggered by being on a set of a music video after she, for the first time in a long time, tried to make music again.
C
8:18Cheyenne RoundtreeGUEST
And in this therapy, she started writing what she wanted to talk about this relationship that had left her scarred.
C
8:25Cheyenne RoundtreeGUEST
And after she finished kind of writing and putting these notes together, she sent it to Sean Combs team and said, I just want him to read it.
C
8:32Cheyenne RoundtreeGUEST
And there also was this offer of, you know, I do want to publish this, but if you want it, you could buy it and you can decide what you want to do with this book.
C
8:41Cheyenne RoundtreeGUEST
And obviously that was kind of a, what we know is a catch and kill that he would buy it and then it would never see the light of day.

Doireann GarrihyHOST
What was the actual experience like and what actually got him put behind bars today?
Bad Boy For Life |Inside the Sean 'Diddy' Combs Trial with Cheyenne Roundtree
18:46
19:00
19:16

Nadine MathesonHOST
Because sometimes it takes you, you know, you can be there present, but it's only when you're doing the writing that in your processing things, then you're like, oh, you're not getting a different perspective of it all.

Cheyenne RoundtreeGUEST
I think one thing that really stuck out with me through the trial, criminal trial, was Cassie and Jane, who obviously were his ex-girlfriends that were victims of sex trafficking.

Cheyenne RoundtreeGUEST
this element of love still there or something that wasn't ready for both of them to kind of completely write him off.
12 MINS LATER
Best Of: Rhiannon Giddens / Investigating Diddy’s Rise & Fall
37:49
37:56
38:08
38:35
47:28
Tonya MosleyHOST
Is that one of the earlier signs of his skill at being, I guess, kind of like a myth maker?

Cheyenne RoundtreeGUEST
I think it was the first instance that he created a persona around himself, and his first explanation was really early on, and it was explained as, oh, he just had a temper and he ballooned up in anger.

Cheyenne RoundtreeGUEST
And then at some point, he didn't even wanna talk about the origin of it, and it's this question mark of, it's kind of an innocent nickname [chuckles] really when you think about as a kid, why would you tell Oprah that you can't talk about it? So it feeds into this mysteriousness that he cultivated at an early age or in, in his early 20s, and then how he was able to shed that as time went on.

Cheyenne RoundtreeGUEST
And the biggest shift we saw was when he went from Puff Daddy, Puffy, to Diddy, um, which came after the criminal trial in 2001 when he was accused of carrying a firearm into a crowded nightclub where people were injured.
9 MINS LATER
Tonya MosleyHOST
And as someone who came of age with Diddy's music, it's almost overwhelming to think that something like this could continue to be pervasive, and we all just kind of accept it.
Investigating the system that protected Sean “Diddy” Combs
30:33
30:44
31:07
31:34
37:41

Cheyenne RoundtreeGUEST
She showed up to court nine months pregnant, um, with her third child, and that visual in itself was really powerful, at least to me.

Cheyenne RoundtreeGUEST
Um, this is a moment she should have been resting and welcoming her first son with her husband, and yet she was choosing to spend those precious moments testifying against someone that she hadn't seen since she broke up with him in twenty eighteen after attending the funeral for his late partner, Kim Porter.

Cheyenne RoundtreeGUEST
Uh, the Combs' defense attorneys made her read aloud these very explicit text messages talking about their sexual relationship and having to sit there as she knew that prosecutors were going to be showing these jurors and the defense attorneys and Combs these pre-cop videos as part of the case.

Cheyenne RoundtreeGUEST
And it was kind of surreal to be in that room watching these two people that loved each other at one point see each other for the first time after so many years and again, a payout, a lawsuit, and kind of the tipping point for the rest of his life.
6 MINS LATER
Tonya MosleyHOST
And as someone who came of age with Diddy's music, it's almost overwhelming to think that something like this could continue to be pervasive, and we all just kind of accept it.
Diddy Do It? Tupac Murder Trial Blows Up
26:02
26:21
26:25
26:47
26:55
41:47
42:08
Nancy GraceHOST
Is it me? Am I going deaf? But did I hear Keefe D repeatedly say Sean Combs ordered the hit? In fact, made a confirmation call after Tupac was murdered saying, was that us?

Cheyenne RoundtreeGUEST
Yeah, that's what he claimed to detectives back in 2008 in this proffer agreement.

Cheyenne RoundtreeGUEST
And actually during the trial, LAPD detective, former detective Darren Dupree, actually they tried to follow this through in 2009 and they sent KVD to New York to meet with Von Zip Martin, who is the alleged go-between guy that knew Puff in New York to try to get this claim corroborated.

Cheyenne RoundtreeGUEST
So there was actually a little bit of an investigation back in 2009 trying to corroborate KVD's claim of Combs' involvement.

Cheyenne RoundtreeGUEST
However, as before, Combs and his team have claimed that he had no part of this and that KVD is just making this up.
15 MINS LATER
Nancy GraceHOST
Am I the only person, am I just screaming in the wilderness, that many state Sean Combs ordered the hit on Tupac Shakur? I don't know why he's not in the courtroom thrown in the pot with the others right now.

Cheyenne RoundtreeGUEST
Well, I think the biggest thing about Diddy's or Sean Combs' legacy is that his ability to kind of wriggle himself out of tough situations.
Sean Combs on Trial
25:47
29:01
29:17

Cheyenne RoundtreeGUEST
Some of these encounters were allegedly videotaped, and when Cassie said that she tried to delete them, that there was at least one instance where a video she thought she had deleted was shown back to her as kind of like this, "It's there forever and I control this."
Lester HoltHOST
Then on March 25th, 2024, his fans and the rest of the music world saw something previously unthinkable: federal agents raiding Combs' mansions in Miami and LA.

Cheyenne RoundtreeGUEST
You just kinda see a surreal scene of this beautiful mansion crawling with federal agents for an investigation that wasn't quite clear what the scope was.