Matthew Cox | Inside True Crime Podcast
Prison Life For Diddy | Inmates Explain Diddy's Prison Experience
19 Oct 2025
Chapter 1: How do inmates perceive Diddy's celebrity status in prison?
I think if they sent Puff anywhere, he would be fine, right?
That's exactly what I told Pete. I said, he's going to pay five guys.
I don't even think he's got to pay. Let me tell you why. Celebrity? No. I think that, number one, you know, the dudes in there, they got cell phones, right? Yeah. So they have been following... The case, of course, from the entire time. And I tell people, listen, federal prison inmates are savvy. Y'all look down on them because you think prison, everybody's in prison is a piece of shit.
But these are some of the most savvy, intelligent people in the world. They have been following this case. There were no minors involved. Right. Which is what everybody thought, right? No gay stuff came out on Puff, right? This was his girlfriend's... Questionable stuff.
There was weirdo stuff, but weird stuff. But yeah, no him having sex with other men.
Cassie testified on the stand some things that may or may not be true because... Some of her testimony, initially when I heard Cassie testify, I thought Cassie was truthful. But a lot of what she said in her civil suit, you know what I'm saying? A lot of that shit was just flat out lies and it came out during the trial. They know that these were his girlfriends, right?
Mm-hmm.
Cassie and Jane. Well, Jane was like a little side piece, right? He was knocking down. And correct me if I'm wrong, you know I'm pro-puff. I don't look at what this Mann Act is as a sex crime like a chomo sex crime.
No, I don't either. But the BOP may.
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Chapter 2: What are the implications of Cassie's testimony against Diddy?
Total shit in what way?
Like, oh, he's messing with kids. He's doing this. He's doing that. But now, of course, it came out and they know it's not true. But some guys just won't back down. No, that just didn't come out because of this. So you've got to have those idiots. I got what you're saying.
They didn't bring it out. The feds just didn't present it because it's connected to Obama or something.
Yeah, some weirdo stuff on there. But you're right. Probably the bulk of them, you're right, And even if let's say even if you're 100 percent wrong and most of the inmates don't, they despise him. The ones that would act on it is very few, very few guys at a low are going to act on something like that. Right. Like, hey, I'm going to take this dude out. OK, for what reason?
You know, like even if one you're probably if you're that mental, you'd never you didn't you aren't at the low long. You you're you're a knucklehead. You got to the low. You're fucked up and you're gone already. Like if you have mental problems where you're attacking people, you're not going to last long at the low because there's chomos everywhere.
So those guys don't – those guys, they're not going to last long, long enough to bother Puffy. On top of that, so let's say you're completely wrong. Nobody really wants him there. Most likely nobody is going to act on it. Even if everybody didn't want him there, they're probably not going to act on it at a low.
And even if some of them were going to act on it, I think as soon as he gets there, first thing he's going to do is go up to five of the biggest fucking guys and say, bro, I'm gonna put 500 bucks on your book right now. Give me your information. I'll get 500 bucks. He puts 500 bucks on, On Five Guys books, they're going to follow him around like security.
Oh, they're going to let it be known. If he paid him, they're going to let it be known. Don't fuck with this nigga, man. Leave him alone. But I think if he went to a spot, where was that political? At a low... The low I was at, it wasn't really that political. Yeah, you know, the different cars moved around, but it wasn't really superly enforced, right? Right.
You didn't have to do it.
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Chapter 3: How do inmates react to Diddy's legal situation?
And she's got, like, a clothing line at, like, Walmart or something now. Or Target or something. Like, turned her into, like, a huge... Turned her into something. Into something.
Like, hey, this... Listen, I think Puff, man, you know, I wasn't... I think he got over-sentenced, number one. You know, he... Well...
Yeah, yeah, I guess I could argue that.
I think I couldn't see the enhancing him, 13 levels of first offender getting enhanced from a level 14 to a level 27. But, hey, what's done is done. We move forward. But I know and you know that he is going to meet, through this experience – some of the smartest people he's ever met, right?
And the relationship in there is gonna be based on reality instead of everyone that he's known since 1993 when he became Puff Daddy, it's all been all fake, right?
Yeah, you can't tell.
I'm going to laugh at this dude's jokes. I'm going to do what he tell me so I can work at Bad Boy or at the Ciroc or at Sean John. Whereas when you get to the feds, that ain't really, you know, people may look at you like that, but it's reality in there, man. And I think he's going to benefit from this thing if he even gets to that point because they're talking about a pardon too now.
I think the over-sentencing issue is that the judge obviously sat through the whole thing. She's seen all the bad behavior. He. Oh, he. Sorry. He's seen all the bad behavior. Is it he, judge?
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Chapter 4: What are the potential consequences of Diddy's prison experience?
I thought it was a female judge. No, it's an Indian dude. I ruined sub-Romanian.
Sheesh. So he's seen all the bad behavior, the, you know, buying, you know, using other inmates' phones. And, you know, he's like all these things that don't amount to anything. But in his mind, he's kind of decided that, you know, he's irritated with them. He's irritated that, well, I don't know how. You know, they'll get upset with you for going to trial and winning, right?
And then you would think that the judge would be like, they offered him 20 years. I don't know if they offered him anything, but let's say they offer him 30 years. For the plea?
Yeah.
30. Yeah. So what choice did you have but to go to trial? You might as well go to trial. You offered me 30. Right.
I'm 55.
Right. You offered me a life sentence. So I could see the judge initially saying, this jerk-off should have taken 30 years. He's wasting our time. But throughout the course of the trial— You would think—and once he wins almost all of the indictments, right, all the charges— The more serious ones. Right. You would think that the judge would say, fuck, he made the right call.
He should have gone. So did he give the court a hard time? Yes. Did he give the prosecution a hard time? Yes. But did he do it because he was innocent? Yeah, he did. So— You would think that, but I don't see that that's the way the judges look at it. I think they're irritated. You're buying. You're buying people's phone time. You're manipulating the system.
You've got guys out there trying to talk to witnesses. Like I feel like you're taking advantage of things. I feel like you think you're above the law. And so as a result, he over-sentenced him. Does that make sense? Like I don't think he did it for a legal reason. I think he did it just because he's irritated.
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Chapter 5: How can expensive gym memberships motivate you to work out?
His name is Tom Simon. And we were talking the other day, and he said, listen, because I was like, I just can't seem to even get into the gym anymore. He goes, you want to get in the gym? You want to really get in shape? And I go, yeah. He goes, go to one of these –
these um you know gyms he said that like weighs you and does everything and gives you a plan and stays on you he said he said that are extremely expensive he goes go spend an ungodly amount of money on one of these gyms he goes you'll go to the gym because every morning when you wake up you'll be thinking to yourself fuck i paid 750 for the next you know if i better get in you know for whatever you know i'm paying 300 a month i'm damn right we're getting up get up
And he's right. For me, we were going to do either Orange Theory or we were going to box.
Chapter 6: What are the benefits of boxing and calisthenics for fitness?
There's a boxing place.
What the hell is Orange Theory?
It's like a group workout. I feel like they ride bikes. I feel like it's kind of like spin class. You do cycles and they track your heart rate during the whole time.
I'm surprised you would do that, man.
You've been to prison, man.
I wouldn't do that. I did the boxing class. Listen, I ain't got no gym membership. I go, see in Jersey and New York, we got a lot of calisthenics parks. So you got pull-up bars and dip bars all over the place. But I go into a Walmart parking lot in the back and knock out 300 push-ups, 200 squats or whatever, 300 jumping jacks. You know what I'm saying? So I ain't buying.
But I stopped lifting weights though. Now I lift weights in prison, but when I got out, I let it go because that shit kept me sore.
Yeah, but that's why you had that, you were probably bulky. I was bulky, right. I was bone thin. I was 150 pounds. Yeah, but you was probably cut up, though.
Oh, yeah, I had abs. All of that. All of that. And see, that's what I prefer. I prefer to look like something, be cut up.
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Chapter 7: How does discipline from prison influence post-release life?
And the gas tank.
Boxing going to give you the gas tank too.
Yeah, yeah. My cardio is just horrible. But we went twice. We skipped today. And then we've got two more. We're doing it four days a week. So we're going to do Monday and Tuesday, and then we're going to do Thursday and Friday. And then probably next week we're going to start going to the gym. Instead, we walked two miles today. You're going tomorrow? Tomorrow morning, yeah. Why?
It's going to be a long day tomorrow. Oh, yeah. Well, we wake up. We go to the 545 one. Yeah, yeah. You go too, Kobe? No. No, but we have three podcasts tomorrow. We have two Tom Simon. We have Wade. My buddy Wade's flying in. I think I might. I don't know. Do I have something at night, too? I don't know. Something. Probably even have a call or something. It's going to be a long day tomorrow.
I work out every day, man. I don't miss a day. That shit is really for my mental health, man. Because it gives me a sense of well-being, you know, focus. And I like to feel good and look good.
And I mentioned this the other day to Jess. We were sitting on the couch doing something and we were talking about, I forget, man, we had just eaten like too much. And we're like, oh, I just ate too much.
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Chapter 8: What lessons can be learned from starting a YouTube channel?
And we're laying there and I go, I said, do you have any idea how disciplined I was when I got out of prison? Talk about it, man. And I just – I sat there. Structured. Absolutely. Structured.
There was – and I was – I would go around my brand new – when I moved into the apartment complex, I would – when I would go to the gym there to work out there because I worked there at that gym before I got a membership because I didn't have any money. So I'm not spending $35 or $40 for a gym membership, which was LA Fitness at the time. And I still have that membership. But –
Instead, I was just, I was like, Hey man, this place comes with a gym, doesn't have everything I want. I'll fuck it. I'll just, you know, like you said, I'll just do burpees. I'll do whatever I can do on my own. I'll use their equipment. What I can, what I can't, I'll figure something out. And so I would go there and, and so I, I, uh,
I would – on my way there, there's a brand-new complex that I moved into. I would grab a garbage bag because as you walk, even through a brand-new – people are just scumbags. People just throw stuff on the ground, and I would pick up garbage. I would stop and pick up garbage. Each time you pick up is a rep for the midsection.
Well, it wasn't just that, but I was thinking to myself, like, I don't want to live around filth. I don't want to live around this. I don't want to be around this. And it wasn't a big deal, an effort. Now, we walk around the neighborhood every once in a while, and I'll see something. I'm just like... It's fine. Somebody will get it. Listen, we drove, we got to our house.
One time we drove by something. It was like a tire on the side of the road. And keep in mind, you saw where I live. I live in a nice neighborhood.
No, I've never been by your house. What are you talking about?
You came and did the podcast there. Sure did. That's right.
That's right. That's where it used to be. Right, right, right, right, right. Yeah, yeah, yeah. Yeah. Somebody left a tire over there?
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