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Diddy's Worst Fears Behind Prison Bars

In this episode of the Two Angry Men podcast, the hosts discuss Sean Diddy Combs' recent sentencing and the implications of his time in federal prison. They delve into concerns about his safety, ...

Diddy's Worst Fears Behind Prison Bars
Diddy's Worst Fears Behind Prison Bars
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spk_0 Are you concerned Sean Diddy Combs could be sexually assaulted violently assaulted because based on what was said in court it feels like a thing.
spk_0 Yeah, it's clearly something.
spk_0 Welcome to the two Angry Men podcast mark.
spk_0 Diddy is going to spend definitely two plus years in a federal prison. I just want to lay this out right now.
spk_0 He is a target because they talked about this in court. They said he's already somebody tried to shank him already and that he is a big target.
spk_0 Are you concerned that Sean Diddy Combs could be sexually assaulted violently assaulted? Is that a thing because based on what was said in court it feels like a thing.
spk_0 Yeah, it clearly is a thing. I mean, they're already and he did not want to make a big deal on it. They already tried to shank him once at the end of the scene and that was thwarted and it happens in prison.
spk_0 I mean, I knew and I could tick off how many times we are aware of somebody getting seriously injured or killed in prison.
spk_0 And so they're going to have to keep him somewhere that he that they can keep an eye on him. It would have obviously been better if he had gotten less time and had been here to camp.
spk_0 But he's going to be in a facility where somebody's going to have to from the the OP and I think, you know, they're well equipped to do it if they can to keep an eye on him because he is a target.
spk_0 So what does he do to do they put him in solitary? Is he with the general population? How is this going to work for two years?
spk_0 Well, the first thing they do is they've got to designate him. That's what he's called. We're going to take a look at what the judge said. They're going to see the order on the docket.
spk_0 If they're going to take the months, they're going to take the offense characteristics. They're going to take some of the other findings that judge said were subrhyming made and they're going to designate him to a location.
spk_0 He's going to be in the MDC for a period of time before he's transferred when he's transferred, then they're going to take all of that into account and then he will be switched from the jail system to the prison system.
spk_0 So what about this? And I know you can't disclose specific conversations because you represent it. But can you give us a sense of the fear factor here on his part because he has they did attempt to shank him already.
spk_0 He knows he's a target. Now he knows that he faces upwards of two years with credit and all. But is he freaked out?
spk_0 Well, I've been talking to him since the sentence. I know in talking to him for numerous innumerable times that I would not say he's operating from a place of fear, although he was during the trial as all defendants are fearful.
spk_0 Nobody goes into a trial. Anybody tells you they're not afraid when they're in trial, just lying to their teeth. But I think post trial, he's he's acquitted himself well and was preparing himself for this.
spk_0 Obviously, I've got a lot to say about the sentence, but in terms of the fear factor, I think it's going to set in. I think over the next week, you're going to see it make some moves. And when I say make some moves, there's things you can do to try to figure out where and what you should do in terms of housing.
spk_0 So the judge gave him 50 months and five oh five oh five oh and where he served 13 and when you look at the 15% credit, it's going to be two years in change that he's going to actually have to serve.
spk_0 I got to ask you something about something that happened in court today and we talked a lot about this on the livestream and I couldn't believe my ears that did he booked a speech for Monday.
spk_0 When I heard that, I thought, yeah, when the prosecution said hubris, it's like, oh, yeah, the judge is going to let me out. It's no big deal. It just it was shocking to me that he would do something like that. It just seemed as tone deaf as just about anything I've heard in a long, long time.
spk_0 You know, it's interesting. There's been there's been a lot of things and obviously because I'm involved, I don't want a second guess. I don't want to lay blame. I might do that next week. But a lot of times you find that people in these situations and high profile people make decisions that aren't the best.
spk_0 And I think amongst them, I know that they tried to clean it up in courtroom afterwards. Who knows the real back story here. All I know is is that I think he is earnest to he being shun about wanting to better himself.
spk_0 I think the prostitutions and a gambit, if you will, by asking her 135 135 months, basically just, you know, between 11 and 12 years, that has this effect of having the brain look to the midpoint. If somebody's at 14 and somebody's at 135, your brain automatically goes to the midpoint.
spk_0 And so there is that tendency that if you go so over the top that you're going to get a sentence that exceeds in my opinion where he should have been. It's also I thought it was going to be I thought it was going to go higher than he did.
spk_0 Yeah, I will tell you this when I set kind of my internal over and under at 39 months going into this. And I thought there's a lot of reasons for our gap programs first step program given the man at comparisons why 39 months that is being the high end of one of the guidelines made a lot of sense.
spk_0 I thought when his honor came out and said that he went through the machinations of adopting the probation offices 70 to 80 whatever that to me said, oh, this is 39s out the window. He's going over 39 months. So I've respectfully lost all the bets for with people who took the over 39.
spk_0 Well, and also what he said was I am going to consider all the violence in the testimony. And when I heard that because you know the defense position was he was acquitted on the charges directly involving violence so the judge shouldn't consider it. And the judge said from the jump. I am going to consider it. And in the end, he said he was appalled by it. And you could just hear it. And literally said to Cassie, I heard you.
spk_0 And so even though he was acquitted, the judge said, I can still consider that it may not be beyond a reasonable doubt for jurors, but it's on the table for me.
spk_0 And what he did was in the argument was that it's what's called acquitted conduct, meaning there was conduct that he was acquitted on the judge said he wasn't going to basically go into that kind of whole line of cases.
spk_0 But he was going to consider it as a factor. And he did consider it obviously is a factor. And he said he was going to send a message basically the terms effects. I always think of my father, whatever a judge says, I want to send a message.
spk_0 My father used to say, shows you how old I am. You want to send a message, use Western Union. But judges do want to send messages in high profile cases.
spk_0 Anybody who says high profile cases, celebrity cases, you get a break. You don't get a break because if this were somebody else who had rolled the dice, so to speak, who had bet their livelihood, their livelihood.
spk_0 And all of his assets on the Rico, all of the life sentence on the sex trafficking and one, instead of the government getting kind of an obstruction or all kinds of other tax tips and service charge.
spk_0 You know, my opinion or what normally happens is the judge would say, well, you took your best shot government. I and you took a swing, you lost. And I'm not going to, I'm not going to let you indulge in being a sore loser.
spk_0 In this case, I think what he did was he said, I'm finding the guidelines 70 through 80, whatever. So now you can argue and go on appeal. If he sentenced within the guidelines that he miscalculated that, but what he did was, and I was telling what one of my partners, as he did that, I said, you watch, he can be intellectually diabolical.
spk_0 The way to insulate this sentence and this appeal is to come substantially under the guidelines that he's accepted of probation, but hammer him nonetheless. And that's exactly what he does. You come in at 50 to 60, it insulates the appeal.
spk_0 Yep. And that leads me to what I thought he was going to do as a Hail Mary. So indulge me for a minute. When, when did he said he wanted to speak, which I knew he would do.
spk_0 So you and I talked about it. Yes. I said, how have we talked about it? I agree. We had to speak.
spk_0 So here's what I thought he was going to say, because at that point, he knew he wasn't going to walk out of jail. He knew he was going to get time and significant time.
spk_0 So here's what I thought he was going to say, your honor, and he does his whole apology and remorse and all of that, and he does it all. And then at the end, he says this, your honor respectfully, I would like to say that I now understand what President Trump was saying when he said that the justice department was weaponized against him.
spk_0 Because I feel similarly, I feel like that's what happened to me, not with a man act, but with all those other charges. And they went into my bedroom, the way they tried to go into President Trump's bedroom, and it was wrong. And I thought that he would throw that Hail Mary to get a pardon. And Donald Trump to me, um, loves flattery more than anything.
spk_0 And if he embraced him in that courtroom, I thought that was his best shot. And it didn't happen. Talk to me about that.
spk_0 You know, people often, I think you are miscast in some quarters, not all quarters, but other people understand what a brilliant tactician strategist you are.
spk_0 Because if he had done that, I might have kind of massaged the message. I think there are, you've heard me talk about this. I think there's incredible similarities between Ditty's situation and the president's situation.
spk_0 I think that's the least of which is the lead prosecutor conspicuous by her absence today. Marine Comie was the one who prosecuted both Ditty and Epstein and whose father who's basically indicted at the kind of dispatch of the president.
spk_0 And there are similarities. They are both in New York. They both had in my opinion, prosecutors who weaponized the criminal justice system against them. And by the way, as soon as Sean heard the fact that the judge was adopting the sentence and guidelines that we just talked about.
spk_0 As soon as that judge said, I'm going to overrule the objections, overrule the idea of that he's going to adopt any of the defense object constitutional or due process of objections.
spk_0 And if I'm Sean Holmes and I'm sitting in that form, I would have just said, you know what, you're right. This guy, his honor was going to hammer me. I'm not going to get, I'm not walking out of here. I don't know. He was her brain scheme. It was to book a speaking or engagement or whatever for next week.
spk_0 I don't care what the speaking engagement was unless it was something that was going to be remote or virtual. That isn't even something you shouldn't have been talking about. And I should have been appealing to the other judge of one who could do something for me is DJT.
spk_0 So why didn't it happen because I look, you know, we had a big argument about this on the live stream today that there were people who were saying, oh, he'd lose his base. And I'm kind of like, I don't number one, I don't know he'd lose his entire base. And you know what, if you lose your base, you gain another base and you're free. And that seems to be what matters.
spk_0 So was this discussed, I mean, was it was it rejected? I mean, did somebody think of it?
spk_0 I can't get into any of that as work product. What I will tell you is, and I'm critiquing the team myself. I thought that the guy was cast when his honor came out and overruled the objections.
spk_0 So at that point, you have to, I always say, my favorite word in the criminal law is fluidity. You cannot, you know, it's the Mike Tyson who was a former client of mine and Mike famously said, everybody's got a plan.
spk_0 So they get punched in the nose. And when you get punched in the nose, you have to remain fluid. You've got to do something. And I'm not second guess in anybody. But this was not, so it's not the finest talent.
spk_0 Not hard to read between the lines.
spk_0 Was there a problem because there were too many lawyers in this case, because I'm just thinking when there's one, you know, you use somebody who has great judgment and there were plenty of people with good judgment.
spk_0 But this felt like a committee. And we talked about this at the beginning. And you kind of dismissed it and said, yeah, well, you know, this happens a lot.
spk_0 But I'm thinking, you have one person saying, do it this way, do it this way. It's easier. It's clearer. And you take bolder moves than when it gets kind of watered down. And that's kind of what it felt like today for me.
spk_0 Look, I love everybody on the team, but I was insistent to the extent I was listened to, which I think was quite a bit that Mark and Jenny run the show. And, and Alexandra handles the appellate.
spk_0 Mark and Jenny should have run the site. So my opinion and I'll just leave it at that.
spk_0 So, um, the appeal seems often, are they even going to bother appealing this?
spk_0 Oh, I, I think it's way too early to do, to make that determination. I mean, you have to let it sit in. I will try. And by the way, 50 months, 50 leaves you open to a number of possibilities if you're in Sean's columns.
spk_0 And he will be consulting with consultants. He'll be consulting with professionals who will give them the advice on that who understand exactly the permutations.
spk_0 But for an appeal, I'm going to go back to the point I made and try to make it less esoteric by giving him 50 months by the judge sentencing into 50 months.
spk_0 So the appeal, I think if I'm a handicap, if somebody comes to me and says, Mark, what do you think about an appeal? So that's Sean Colm just somebody else, the judge found sentencing guidelines that were over 70 and the judge went under by 20.
spk_0 And then I'm asked, I went to trial, I lost on a couple accounts and the judge went under what probation suggested the guidelines are, I would tell you that an appeal is incredibly and incredibly, it's always a heavy lift.
spk_0 But it just becomes a perky lean lift because of the way the judge did it. And by the way, I've said this a couple of times. This is not a judge who this job was a upgrade.
spk_0 He took a massive pay cut. He was an accomplished litigator. He has a pedigree that the most lost students would envy and he's a very, very brilliant man. And if you don't think he thought this through and understands nobody, no judge wants to ever reverse.
spk_0 And this is about as insulated a sentence as you can get from an appeal having said that on the man act itself, be left some wiggle room open for the constitutionality of the man act as applied.
spk_0 That's set, that's a separate grounds for appeal than the sentence itself as far as the sentence itself. I just think that's a lift. That's a bridge too far.
spk_0 So a lot of defendants in his position would get a prison consultant. And I would think that you've gotten one for him already that he's talked to them.
spk_0 And I would think he's talked to them. I want to go back to the safety issue that, you know, did he, you know, and the judge seemed to buy it. Did he sexually brutalized these women?
spk_0 You may not say he did or and did he may not say he did, but the judge clearly believed it. So that puts an even bigger target on his back, you know, to be sexually assaulted in prison, to be violently assaulted.
spk_0 So was this addressed by a prison consultant yet does he have one? Have they talked?
spk_0 Look, I, I talked to prison consultants. I want to say at least once a day or I profile and no profile clients. I think prison consultants are one of the essentials. Don't leave home without them.
spk_0 So to speak, don't go to prison without one. They, and I say this because they tell you and normally I mean, you think somebody like Craig, I told you, one of our, one of the top two or three, if not the top.
spk_0 They understand it because they've lived it and they get it and they know certain things that you just can't know having been on the outside. It would not surprise me if I, at a certain point, what's another client of mine entitutes him just to give me some guidance as well or another two clients because there are things you have to do.
spk_0 You have to look forward. We can't look backwards, but you're, you know, Harvey, I hate to say it, but the reality is the only thing that's more, yes, when we go to prison is a child of murder or child sexual predators.
spk_0 That's right. And so I don't feel I'm raising this crazy hypothetical when I say, no, it's not, it's not quick bait at all. You're, you're, you're having a discussion.
spk_0 It's a very hard discussion that criminal defensitors have to have weekly, if not more often.
spk_0 So you talked to these prison consultants all the time. What would they say to a high profile person like this about avoiding sexual and violent other violent assaults?
spk_0 There's all kinds of things that I mean the first and foremost is where do you get designated that I can't emphasize enough that so for you do anything in terms of preparing yourself.
spk_0 You have got to take your best shot as designation. Now you have some control over that. And when I say you, I'm talking about kind of the royal we meaning the court.
spk_0 You're lawyers can aim form can bring stuff to the attention of those who make the designation. You can send them material. You can try to point out things.
spk_0 So ultimately it's the end of the day. That's a decision that is made internally. They have their own protocol. They've got their own checklist, so to speak.
spk_0 And they're going to designate you at a spot. Now you do have remedies. If you get designated to someplace you don't necessarily think you belong.
spk_0 I've had clients who challenge that successful when they've been designated. They think it was because of a misnomer or a misclassification.
spk_0 And they've successfully done it. But sometimes be careful what you wish for. You got a little kind of what I would I call it L.A.
spk_0 Arlen's freeway therapy where okay, you want to go someplace that's not as onerous. We're going to send you someplace where you've got no relative anywhere near you because you challenge less.
spk_0 I don't want to say it's punitive, but it's punitive. And so that is the next kind of effort that's going to be made is to determine and to handle where the designation is and I'll bet your TMZ breaks that news as to where the designation is probably within minutes of when they make the designations.
spk_0 So let's say he is sent to a minimum security prison. Is he out of the woods when it comes to that kind of assault?
spk_0 If you're going, you know, you and I talked about Gillette Maxwell who went from the one place in Florida, which was a higher level.
spk_0 And she was transferred after she did the interview with a couple day interview. She was transferred to a what they call a camp in Texas, which I'm familiar with.
spk_0 I've had other clients in so a camp is generally one of the better places to be and the reason for that is because a camp is basically you get certain privileges.
spk_0 And if you step off of the line, so to speak, if you violate, if you do anything that is not kind of holding the oil, they will immediately send you someplace a lot more onerous. So that's why I say, in the long winded answer your question.
spk_0 Yes, you've got to get designated somebody. You know, I know he wants to be New York adjacent. If I'm Sean right now, I'm going to be angry for someplace like long, pop, satellite camp or something along those zones.
spk_0 But that still does an answer is he out of the woods when it comes to being sexually or other or in any way assaulted by being in a minimum security prison.
spk_0 When you say out of the woods, it greatly, look, you're never, it's a prison anywhere you go as a prison. You always have to watch your back literally. And if that's the case, you're never really out of the woods until you're released or you go to a halfway house when you get into one of the programs.
spk_0 But if you are in a camp or in a low levels designation, your odds go down dramatically. I mean, you and I, there's no, I just saw a buddy among didn't wake up substantially younger than you and me over last weekend. So there's no guarantees you're going to wake up in the morning.
spk_0 So there's never any guarantee, but if he gets designated at a what they call a satellite camp or one of the low security institutions, it's a lot safer for him.
spk_0 So he is used to calling the shots. And you know, I don't know how much you can talk about this because I mean, he's your client.
spk_0 But I know that people who call the shots when suddenly others are calling them for you. And you are suddenly a number rather than a king that it's hard.
spk_0 Do you have any concerns that he's going to have a really rough time following the straight and narrow while he's in prison?
spk_0 Well, I think he's, I think he has, I've seen a person I think he's changed dramatically while in the green, the jail, which he's not a prison, I make that distinction.
spk_0 Reconviction post conviction, reconviction jail post conviction person. So he has changed dramatically. However, there's always that tendency. It's in the personality.
spk_0 I mean, you're 55 years old like Sean six, be some odd like me 70 some of like you. It's very hard to change all the habits. And the judge kind of said that in as much today in a different way.
spk_0 In a different context, but it holds true everywhere. You're going to have to fight against that urge. You're going to have to fight against them. It's Sean said something that I thought in his statement was that it was humbling. And clearly it is humbling.
spk_0 And I will tell you are the new unit with a lot of the people that you followed over the years. There's various avenues that you can take. There's various decisions you make when you're in custody.
spk_0 And you know, I always tout the man end as brothers is making good decisions. There are others that I've had who made incredibly bad decisions. I've always hope that somebody makes for good ones.
spk_0 Yeah. So if you had to put this on a scale, 10 being on he's in huge trouble in prison and one he's going to be fine.
spk_0 Just in terms of the next two years for him in terms of the dangers of being there, the difficulty of being there. What number do you put it at?
spk_0 A four really a four. Yeah, I think and you might have me reassessed once he gets designated. But right now I don't have I mean I was fearful when the judge took the probation guidelines recommendations.
spk_0 I mean I was on I've been on a rollercoaster all day on this. I was on a rollercoaster yesterday on this and it's been very hard to handicap this and that's.
spk_0 And I know and when I say handicap it's because I'm so incredibly close to it and I'm constantly when you have one of these cases and we're truly in it in some way, shape or court.
spk_0 You're trying to always give the best advice you can and in this case, I can second guess or always second guess, not just this case, only case.
spk_0 But I'm hopeful that he gets designated to a place where he can continue to do the work on himself, which he needs to do. He's the first guy to admit he needs to do the work on himself.
spk_0 Even post conviction he hasn't made all the best decisions and he would be the first to admit that he's made some really good decisions, but he's going to have to continue to work on that daily.
spk_0 It's not a you don't just look a switch and change. It's hard work and he's doing the hard work and I hope he continues.
spk_0 Okay, and finally, and I don't want to put you in a difficult position if you don't want to answer it, it's fine.
spk_0 But the defense did an amazing job during the trial. I mean, they just did and they won.
spk_0 I don't think they did a good job in the sentencing hearing and you know, I thought the video they played was too slick.
spk_0 They put music on it. It didn't feel authentic to me. The idea of allowing him to book a speech on Monday was ridiculous.
spk_0 They avoided the playing the trump card even up to Slee. There were just a number of things.
spk_0 And I'm wondering what was the difference because it was basically the same crew. Why did it feel so different to me with the trial and then the sentencing?
spk_0 There's no way I can answer that question except to say Harvey or a various student server and the human traditions.
spk_0 I'll leave it at that. I don't want to put you on the spot, but I saw something radically different today.
spk_0 I'm leaving the top. I'm good to see you. I'm coming back. Have a safe flight.
spk_0 Thank you. Bye.