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Foreign welcome to this episode of Kennedy Saves the World. The world might soon need to be saved from Diddy, Sean, Puff Daddy Diddy. Diddy or not, Combs is going to be a free man in a few years. He was sentenced to 50 months in prison, 13 of which will be time served. So he's going to be in the who's Gal allegedly for the next three years. Some people say that's not long enough. Other people say for procuring some oil drenched male hookers, that's too much time. And of course, his legal team is going to mount a hearty appeal in this case. So let's talk about the sentencing, where he goes next. He wants to go to Fort Dix. I bet he does. I heard some of that testimony from the man whores. I bet he wants to go to Fort Dix. Josh Ritter is joining me now. He's a criminal defense attorney and he is the host of two podcasts, Courtroom Confidential and True Crime News. The sidebar reports Josh Ritter is also a newly minted FOX News contributor. Josh, welcome to Kennedy Saves the World.
B
Oh, thank you so much. It's my pleasure.
A
The pleasure is mine. So first, let's discuss. A lot of people were surprised that based on the lurid, salacious, disturbing testimony, they thought that he was going to get more time, but he wasn't convicted of the charges that would have earned him a life sentence, essentially. Was he overcharged?
B
Yes, yes, unfortunately he was overcharged, but he was also under sentenced. I think the, I think the sentencing by the judge was weak. I mean, honestly, yes, he was looking at life on the charges that they did not win, but he was still looking at 10 years apiece for the two charges that he was convicted of. So the idea that as you just laid out, he might be out in three years is incredible to me, especially to given everything that we know. I know that he was only convicted of, of a couple of charges, but the judge saw so much more, including that video with Cassie. And the idea that he was willing to give him, in my view, incredible leniency is pretty astounding.
A
So the judge sort of showed his hand at the sentencing hearing and it sounded like he was leaning toward what the prosecution was asking for, which was, you know, somewhere around 70 to 75 months in prison. And people thought that he was going to get upward of that. What do you think the factors were that led the judge to giving him a little bit more leniency?
B
You know, I don't know and I think you're right. First of all, the Judge did not allow him bail in between the time of the conviction and sentencing. That was kind of the first indication that the judge planned on giving him a pretty heavy prison sentence. And then the judge did make several comments that made it sound like he intended to send a message. And the prosecution was asking for 11 years. Even the probation department had recommended more than what the judge gave him. So, I don't know. The judge, in all his comments, talked about sending a message, talked about how he lived this life of privilege, how he had to understand that everything that he had done up until this point was wrong. And, you know, he's speaking for the victims, and then he kind of limps in there with a sentence that, listen, I, I don't want to go to prison for four years, but I still think that given what he did and what he was convicted of, the judge could have gone far above that, but he chose not to.
A
I know that there have been whispers that mysterious bags of money showed up for potential witnesses who did not testify in the case. Is it possible that the judge would have been influenced by an external factor?
B
Oh, God. Listen, would you put it past this man to attempt that? I don't think so.
A
No, I would not. I would not put it past his team to do whatever they can to secure his freedom because they still see a path forward to monetize this entire episode.
B
Oh, 100%. We're going to be watching some reality show based upon his time in prison. If they don't get cameras into the prison already, maybe that's why they're asking for the certain prison that they are. But I absolutely see him already scheming with his PR people to plan some sort of remarkable comeback from all of this. But I, I got to put a little bit of faith in this judge that, that, that some, some back, back alleyway bag deal was not taking place here. But I would not put it past Diddy's people that they thought about it, that they had some. They had some conference calls about it.
A
Yeah. And, you know, talk to people like, who knows the guy? You know, do we. Do we know his gardener? Do we know his neighbor? Do we know his tailor? Is there anyone that can maybe have their little palms greased with some baby oil in order to give us a sentence that's a little bit more amenable to getting out before Diddy is completely white haired? And it's, you know, it's kind of scary for advocates for victims of domestic abuse to know that this person is going to be on the street in three Years. Do you think that some of his victims, those who testified in court and those who have filed suit, and maybe even those that are still silent, are they scared now?
B
I think so. I mean, this, to me, this is a win for this man. I mean, you, we talk about, oh, is he going to be contrite? Oh, has he learned his lesson? I don't think so. I think that he might even be emboldened by all of this. He was looking at life in prison. I had said that when he got arrested and he was denied bail, that was the last time he's ever going to breathe a breath of fresh air. And I'm completely wrong.
A
And you're a criminal defense attorney.
B
I thought it was game over for him. I mean, the feds usually, by the time they bring charges, especially in a case of this high profile, they've got all their ducks in a row. And so it was pretty astounding how their case kind of fell apart. And I think it was, to your point that they overcharged it. And now the idea that he's going to be out in three short years, you know, memories. Memories can be pretty short, especially when you have basically unlimited funds and unlimited power. And I can imagine I could see him, you know, a few years down the line after the dust has settled from all of this, him starting to say, you know what? A lot of people turned against me. Where were all my friends when I needed them? How come these people didn't come to my aid? And how come these people testified against me? And it may not be outright violence, but, you know, he's still going to have some persuasion and power in the entertainment industry, and who knows what strings he might be able to pull.
A
Do we know how much money he still has?
B
I mean, every. He still has everything because they didn't seize any of it because this wasn't a financial crime. So he still got everything. Short of whatever the million or few bucks he paid his attorneys. He didn't have to fork over any money for bail because the judge denied it. So that actually saved. Saved him some funds. I mean, yeah, a lot of endorsement deals have left, and there's money that future money has gone out the door. But everything he's made up until now, you know, you got to imagine it's. Is he a billionaire? I don't know. I mean, it's got to be close to it.
A
I think on paper he was, but, you know, a lot of that was probably contingent on future deals and future sales, certainly with Diageo spirits. But now, you know, it's like you look at this and he's going to have three years to contemplate it. He wants to go to a minimum security prison based on what he was convicted of. Is. Is that the typical path for someone who's received the sentence and the conviction that he has?
B
Unfortunately, yes. I mean, it's not considered a crime of violence. What he's been convicted of it. That's what's funny is that the, the crimes that he was charged with required. You know, you have the racketeering charge, but then you had the trafficking charge, which required either force or fear. The jury didn't find that to be true. So what he was convicted of, you know, what we consider the man act or this transportation for, for prostitution, doesn't require any of that force or fear, just requires the actual act itself. And that's why I think it was so straightforward. They were able to prove it in this case, but because of that, it's not considered like a violent crime that might put him into some high max security. So, you know, the Department of Prisons, federal government's going to make those decisions, but I don't think the request for some sort of low security federal prison is, is something that's entirely extraordinary in this case.
A
Yeah. And he wants to go to Fort Dix in New Jersey, not only because it's a fun name to bandy about, but also they have a rehab program. Do you think he's. He's serious about sobriety and getting treatment for his substance and sex addictions?
B
I hate to be so cynical, but I mean, I read his letter to the judge and he talks about how he lost his way, and then he, you know, he puts together this highly produced video to play for the judge. To me, that is somebody who's for so long been able to either charm his way out of trouble, buy his way out of trouble, threaten his way out of trouble. It's not somebody who's truly contrite and truly, you know, turning over another leaf. I think that all the tears that we saw from court, you know, from the illustrations, is a guy who's now realized he's out of options. It is not a person who's realized that they've got real problems because he had real problems. He lost his way for decades. That, to me, is not somebody who's lost his way. That's somebody that just got caught.
A
I don't know if he, if he ever had a way to lose.
B
Yeah, yeah, yeah. I mean.
A
Okay, now I want you to put your defense attorney hat on and, you know, I'm sure you're able to look at this case as a rational person, a father, someone who has studied the law, but now as someone who defends unsavory individuals. It's really not about their moral character. It's about finding holes in the federal government case.
B
Yeah.
A
So what holes presented themselves to you?
B
They made a very interesting argument here about the crime that he was convicted of. Again, it's the man act, but it's the idea of transporting someone across state lines for the purposes of prostitution.
A
Their argument, throwing a couple of gigolos right in the. The back of the pickup truck and just driving to Arkansas.
B
Driving to Arkansas and having a good old time. Oh, yeah. Their point was, listen, he didn't actually participate in the prostitution. He videotaped it. So in that respect, he's much more a pornographer than he is a person participating in prostitution. That this law wasn't really designed for his conduct. His conduct is much more an exercise of his First Amendment rights to videotape and per. And. And record these types of performances. That. That even hurts my tongue coming it out, coming out of my mouth. But it's a clever argument. It really is. And it might have some receptive ears when they get to an appellate cord. But the funny thing about it, by the time this works its way through appellate courts, I mean, he might have served his sentence at that point, but I, you know, he's got unlimited funds. He'll continue to fight it.
A
Don't go anywhere more. Kennedy Saves the World right after this.
B
It's Will Kane Country. Watch it live at noon Eastern Monday through Thursday@foxnews.com or on the Fox News YouTube channel. And don't miss the show. Listen and follow the podcast five days a week at foxnewspodcasts.com or wherever you download your favorite podcasts.
A
That's interesting. You know, it's like I'm. I'm always intrigued and, you know, an advocate for protected speech that's protected by the First Amendment. And, you know, there obviously is an argument for making and enjoying pornography, but those hookers didn't procure themselves.
B
Right.
A
It's not like he just showed up with a video camera and went, oh, my God, there's Man Horse here. I love it. That's so fun. Is it my birthday? It's amazing. Like, I. Hookers are gross. Ew. But I mean, as long as we're all here, I happen to have some baby oil and lube in my backpack. Let's do this. Like, that's so far fetched because you had his former assistant and his girlfriend. Like, he, he decided which guys. You know, it's like, and these are people who are obviously operating under romantic and professional duress.
B
Yeah.
A
And they're like, you know, yes, I gave him the drugs because he threatened to kill me. You know, it's like, yes, I let a male prostitute pee on me because he had abused me to the point and dehumanized me. And I felt like I was nothing. I had no self worth, no self esteem at all. You know, those aren't people who are like, I'm gonna get Sean the gift that he's always wanted and that's a second penis in the bedroom.
B
I mean, it's. It's so sad to be that cardigan. It's so sad because it's so difficult from a prosecutor's perspective to get people, victims to testify in these types of cases. I know from experience, just convincing somebody who's been abused and brutalized in this type of way to be like, I need you to come to court. I need you to talk about the most awful thing that happened to you. And by the way, somebody's going to cross examine you about it. And here you have Cassie, who's been through about the worst type of abuse that we can all imagine, systematic and ongoing for years. She's eight months pregnant and she's still brave enough to go in there and testify in one of the most high profile cases going on in the country against an incredibly powerful man. And despite all of that, the jurors didn't. I don't know if they weren't convinced by her or if they didn't feel that it was enough, but I really feel bad for her that she went. You know, she was so brave to go through all of that, and it just didn't pay off the way she was hoping.
A
Yeah. And, you know, she just, she knew in her heart that if she told the world. Right. What she had been keeping to herself for so long, that they would. They would see the depravity, they would see the inhumanity, they would see her pain. And there is no way that they would let that man walk another free day in his life.
B
It was on videotape.
A
You know, it's like that's what millions of dollars in defense attorneys buys you is they go through everything and they craft arguments like, well, look at the text messages she sent to him. You know, she was asking for it. And, you know, all it takes is a little bit of doubt in one or two People's minds. And like, yeah, you know, that is pretty gross. Like, if it's as bad as she said, then she would have left. Same thing with Nicole Brown Simpson. You know, the jurors in the OJ Case looked at that and went, well, you know, she should have left a long time ago. So I really don't feel bad for her. And unfortunately, that's how some people are conditioned to see the world. And it sucks, and it's totally unempathetic. But I also think that's sort of a flaw with the prosecutors. And James Comey's daughter is not anticipating that.
B
Yeah, it's, it's, it's hard to explain, and it takes some real skill, this idea of what is a circle of abuse and why would people behave in a way that, you know, I imagine these jurors are saying, well, listen, if anybody ever asked me to participate in something like that and they were having, you know, all these depraved acts done to me, I would just walk away. Well, would you? Would you.
A
Would.
B
Do you understand the situation she was in and the coercion and the power and everything else and this idea of the cycle of abuse and how afterwards. Yeah, she may have sent some text messages that don't seem logical, but what does that mean psychologically? That was going on in her head. And they called an expert, the prosecution did, to try to explain that. But I just think, to your point, it's a, it's a flawed understanding and empathy of what these women really go through.
A
Yes. And, you know, it's like so much of it boils down to jury selection, and it, it's interesting because normally these federal cases have a much higher conviction rate. What do you chalk that up to?
B
No, I mean, normal. Like I said, usually the feds. The feds pass up so much, and usually by the time they decide to file something, they have done all their groundwork and they are ready to go. And the case against you is absolutely rock solid. And especially in a case this high profile, they're not going to. They, they knew the second they raided his home in LA and Miami, they knew the firestorm they were going to light off. And so they must have known that they had, they better have their, their, their case ready. And I'm just, I'm kind of shocked how they did seem to overextend themselves, especially when it came to this idea of racketeering. They just, they were trying to convince us that this guy, who's a maniac, but he's a maniac for Himself. The idea that you're going to make this a criminal enterprise and everybody who's involved in it has this overall arching goal. And that goal is what? To help Diddy gets his rocks off. I mean, it just didn't kind of make sense.
A
But they also, they didn't. They didn't outline the enterprise, which, if there's an enterprise, there's more than just one guy. Like, where are you at the head of the syndicate.
B
Right.
A
But you know, who are the lieutenants, you know, who are the captains?
B
Especially his. His right hand girl. I forget her name.
A
Christina Corum.
B
Right. Where was she? I. I thought.
A
I've been asking that this entire time because people I know who have known him and been in his inner circle and music and liquor and everything else, you're like, she's the Chief of Staff.
B
Yeah.
A
She's the one who knows everything. She's the one who would supply him with everything. Allegedly. According to testimony. So why didn't they go after her? What, did she have an immunity agreement with the Feds?
B
Well, usually when you see these cases where it's talking about racketeering and conspiracy, it'll be the United States versus about 12 different people. Right. Instead, this was us versus Sean Combs and full stop, which made me think that means everybody's cooperating and we're going to hear from all of those unindicted coconspirators and we're going to hear from her especially. And when we didn't, it made me. I don't. If they're getting immunity deals, the immunity deal would be for them to testify. So why didn't they testify? And if they're not getting immunity deals, why aren't they indicted? It just kind of. They seem like a very glaring absence from all of this.
A
Do you think that if he had been convicted of everything and he had been put away for life, they would have gone after her next? And now that the big charges didn't stick, now they. They don't have enough powder to go after her.
B
Maybe. But I also think the smarter strategy would have just been if she's not cooperating, then indict her, then just make it people versus Diddy and her or whoever else wasn't going to cooperate. But, you know, you got to imagine that they spoke to everyone and gave them a choice where, you know, which. Which side of this do you want to be on? And I can't imagine they chose the Diddy side. And if they didn't, again, you would have expected them to be witnesses in this whole thing. Maybe, maybe they bring charges on her. But like you said, they've lost the momentum. Now, now, now, now. There's no enthusiasm behind this case.
A
All right, well, we'll see what happens. Josh Ritter, thank you so much for your time. Diddy did the crime he's now doing some of the time, not that much. He'll be enjoying himself playing cornhole and knitting himself a lovely Christmas scarf, I'm sure. Josh, we will see you on the Fox News Channel and all of your podcasts. Thank you for being a part of this podcast.
B
You're the best. Thanks so much.
A
You are. Thank you. This has been Kennedy Saves the World along with Josh Ritter. Kennedy listen ad free. With a Fox News podcast plus subscription on Apple Podcasts and Amazon prime, members can listen to this show ad free on the Amazon music app. Oh, go ahead and leave me a review while you're there. I'd love to hear what you have to say. You've been listening to Kennedy Saves the World on the Fox News Podcast Network.
Podcast Summary: Kennedy Saves the World — "Diddy Did It!"
Date: October 8, 2025
Host: Kennedy
Guest: Josh Ritter, Criminal Defense Attorney and FOX News Contributor
In this engaging episode, Kennedy delves into the recent sentencing of music mogul Sean "Diddy" (Puff Daddy) Combs, who received 50 months in prison (with 13 months time served) following a high-profile criminal case. Joined by criminal defense attorney and FOX News contributor Josh Ritter, Kennedy dissects the charges, sentencing, legal strategies, and wider implications—interweaving wit, skepticism, and empathy, especially concerning Diddy's victims and the public's reaction.
Josh Ritter:
Kennedy:
The episode maintains a sharp, irreverent tone, blending legal insight with dark humor and skepticism about both the justice system and Diddy's intentions. Kennedy's quick wit and uncompromising empathy for victims balance out the legal nuance provided by Ritter, making for a lively and thought-provoking analysis.
For Listeners: If you missed the episode, this summary offers a deep dive into not just the legal outcome of one of the year’s most notorious celebrity criminal cases, but also the broader cultural implications, all served with a helping of Kennedy’s characteristic candor and humor.