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Hey there, folks. It is Friday, January 9th, and yes, Diddy is sitting in prison, but things actually just got worse for him. And with that, welcome to this episode of Amy and TJ Just got works robes because he has very few options for getting out of prison. And one of them apparently just went away.
A
It's coming out of D.C. yes, it is. And look, we have been waiting to see if President Trump would pardon or consider pardoning Diddy. This has been on the table from the get go. Before his trial, did, during his trial, after his trial. He has been asked, the President has been asked repeatedly, hey, would you consider pardoning Diddy?
B
And he was asked one more time by the New York Times. And this was the one. And the reason we were hopping on giving the update robes is because he gave an answer like he had never given before. And we're actually getting the most official, I guess, response and confirmation that a request has been made.
A
That's right. So Trump has revealed for the first time ever that Diddy actually sent him a letter asking for a pardon. And for the first time ever, we heard the President say he is not considering granting Diddy's request for that pardon.
B
I mean, that's, look, his appeals are going on and his lawyers are the best in the country and are making the best legal arguments. But if you were a betting man or a betting woman and you were in Vegas and you put your money on which of these two is his best option, a lot of people might have put their money on a pardon from Trump.
A
Absolutely. And look, we have been hearing from him and we'll get into some of the back and forth, but the President had not shut the door. And you were even saying by the language he chose with the New York Times that he might have still left a crack open for the possibility perhaps in the future.
B
Obviously, he, I say obviously it's, it's obvious to me. But we speak on Rosie's. The headlines are everywhere this morning and folks will see them that say Trump says he is not going to pardon Diddy or Trump shuts the door on pardoning Diddy or all those things. And you could read it as such. But his language, robes. He didn't say, I'm not going to pardon this man. He chose his words carefully. And they could be true. I am not considering pardoning him. Which is a statement steeped in present moment.
A
And not considering him doesn't say I'll never consider him or I won't consider him in the future. Just right now, I am not considering. And he didn't say right now, but you could infer that that is a part of that sentence. And look, this letter that we're hearing about. So when he tells the New York Times that he asked me for a pardon through a letter, obviously the next question from the New York Times is going to be, can we see it? And in fact, President Trump beat them to it. He said, oh, would you like to see that letter? He knew exactly that. Obviously, reporters have been chomping at the bit to try and find out where his head was. But now to be able to see a letter that Diddy wrote to the president to see where Sean Diddy Combs head is and how he asked him and what he said, that that would be reporter gold.
B
I don't know if we'll see it. It felt like one of the things, once again, that Trump is very good at dangling over the press and keeps our focus right there for a little bit. And I got the impression, robes, you tell me that this was a letter. This wasn't a legal letter. This wasn't something written by an attorney. This was from Diddy personally.
A
It did seem that's what he, the way he said it, it did sound as though Sean Diddy Combs personally wrote President Trump a letter teasing the reporters, would you like to see the letter? So of course, the reporter said, yes, but then they made it very clear in the article that President Trump, in fact, did not produce that letter for them. And then they said after the interview they went back and they asked for a copy of the letter or they asked the White House, could you even give us a description of its contents? We'll take that, too. The White House just referred reporters back to his original comments that he is not considering pardoning Sean Diddy Combs. So they also tried to go through Diddy's lawyers. They too did not respond to a request for a comment about the letter. So they were just trying to get some corroboration or at least some idea of what Diddy said in that letter.
B
This is significant after what we saw last year after, I mean, this was the talk of the tier the year, at least from a legal standpoint, was it not?
A
Absolutely.
B
It had implications of race of the entertainment industry, power, men, abuse, physical assaults, responsibility, coercion. I mean, you keep going and going. It just had all of these elements to it that had the whole country talking, not just about some baby oil, but we were having real conversations about what this meant and responsibility and friendships and who should step in and women. And this was everything. So to think that the guy at the center of all of that might possibly end up walking out of jail way early is top of mind for a lot of people and relevant to the justice system. So to. To hear that one of his, what some would say best options might be off the table, it does bring this to a. To a level.
A
It certainly does. So he loses what, yes, many would consider his best or easies path out of prison. But a lot of us, I mean, we mentioned it, but we didn't focus on it because it was on Christmas Eve, December 24, that Diddy's lawyers made that official appeal. So they appealed his conviction, and they also appealed his sentence. So his attorney, one of his attorneys, Alexandra Shapiro, I thought this was interesting in the filing, on Christmas Eve, this is, this really is his last day ditch. This is his last chance at getting out of prison. So in the appeal, in the filing, she said called his sentence unlawful, unconstitutional and a perversion of justice. And she asked the appeals court to consider two things. First of all, just to actually throw out his conviction entirely. But if the appeals court decides not to do that, they're asking for him to be resentenced. And, and that's interesting because they are going after the judge in this case. They said that the judge did not properly follow sentencing guidelines when sending him to prison for 50 months. That was his prison sentence. They actually used this word. They said the judge flouted new guidelines and improperly considered conduct for which Combs had already been acquitted. When they, when the judge formulated his. His sentence. And we've talked a lot about this.
B
Yeah, I mean, the judge was, I mean, the judge wasn't shy about it. He says, yeah, I know these things. You weren't the most serious charges he was not convicted of. He said, still, I am. I think you're a bad dude who did some bad stuff. And I'm still going to consider stuff you were not convicted of in your sentence, which, I mean, just from a layperson sounds wrong, but I might not be legally wrong, but it's sounds wrong.
A
Yes. So in the filing, Diddy's attorney said that the judge acted as a 13th juror. Exactly to what you're saying. So he acted as the 13th juror in the case. And they called the sentence draconian so they are going after this judge in a way that they haven't before because up until now they've been trying to appeal to that said judge.
B
Yeah, he was literally his judge. I mean, he was judging him on everything. So yeah, they were very kind to him and great judge. Did he even have nice words for.
A
The judge said he's been doing a fabulous job right before the verdict. Yes, he was doing his best to try and butter him up. It did not work. Yes. Cuz in September, just a few months ago, you remember, this was the other effort they were making to try and get him out of prison. They were actually appealing directly to that judge. They said, hey, he was convicted under the Man Act. This was not an act that was intended for its current use. This is an act just steeped in racism. And this was not the original intent of the law. And it was applied to Diddy to get these longer prison sentences. The judge said, nah, too bad. So sad. So that didn't work. Appealing to the judge. So now they're appealing to a federal appellate court and they're throwing the judge under the bus.
B
Yes, appealing to an appellate court. But no longer can he appeal to maybe President Trump who now seems to be saying he is not considering pardon. But would you believe, folks, we have to go back maybe, I don't know, 10 years to get the answer as to why Diddy isn't at home chilling in Miami right now. Yes, it has to do with his relationship with President Trump. And if he had just done a few things differently all those years ago, he might be home. Stay here, we'll explain.
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All right, we continue here on Amy and TJ on this Friday, January 9th. Just getting word from President Trump that he is taking away at least one what some thought was a pretty decent option for getting out of prison for Diddy, which was a presidential pardon. President Trump telling the New York Times in an interview that he is not considering pardoning Diddy even though he is now acknowledging Diddy did officially send him a letter asking for a pardon and robes. He's going back and forth. We talk about how much he has kind of teased the press when asked a question about pardoning Diddy. And he has given some insights into their history and certainly into how he now views their relationship.
A
Yes, we have so many quotes over the past several months from President Trump that were teasing where he might be leaning when it came to whether or not he would pardon Diddy. But he did make it clear that they did at one point have a friendly relationship. He said, I'm gonna quote the president here. I was very friendly with him. I got along with him great and seemed like a nice guy. I didn't know him well, but when I ran for office he was very hostile. That is the key point here. So everything was good until 2016.
B
Do you remember what he, what Diddy said? There was something out there, but I can't remember it being that harsh. Or maybe it was he took it personally.
A
He did take it personally. And I don't know the exact comments that Trump is referring to, but he says that Combs made some nasty statements about him at the time when he was running for president. He said that Combs used to really like me a lot. But that relationship busted up. And so here are a few other things. He said that we could read the tea leaves, but he always left open this possibility that he might consider it. So he said, I haven't seen him. I haven't spoken to him for years. I don't know. I would certainly look at the facts. If I think somebody was mistreated, it wouldn't matter whether they like me or don't. Do you believe that? No, I don't either. Because then he kept saying other things that belied that last statement. Um, he said after the Diddy verdict, I had not heard this one before. Tell me if you did before. But President Trump said after Diddy was convicted of two of the lesser accounts, he said, well, he was essentially, I guess, sort of half innocent. I know what they do still in jail or something. But he was celebrating a victory, but I guess it wasn't as good of a victory.
B
Yeah, I don't remember that one.
A
I don't at all.
B
That one didn't make a lot of headlines.
A
No, it did not. But he said, we're human, human beings. We don't like to have things cloud our judgment. Right. But when you knew someone and you were fine, and then you run for office, and he made some terrible statements. So, I don't know, it's more difficult, makes it more. I'm being honest, makes it more difficult to do when it comes to pardoning someone. So, to me, that was the point. He. And I thought about this when I read the headlines that Trump has now said he's not considering pardoning Diddy. He. You know, when you first go into the workforce, someone always gives you this advice. You meet the same people on the way up as you do on the way down. And if Diddy had just remembered that, maybe he'd be in a different position right now. When he wrote that letter to President Trump, if he maybe just hadn't said, I don't know, made a comment about the political race, this might just be a warning. You never know. You never know whose help.
B
You're going to need lessons today from Diddy and Trump, but that is 100% correct. When you think of the possibility that Diddy could be home right now in that $50 million home, if he had just 10 years ago not said anything about Trump running for office or not said anything nasty about him running for office or supported him, it's incredible to maybe think about where he would be. And so, yes, maybe that's the lesson. Just be careful.
A
Yeah. I mean, the thing is, you. You imagine, I mean, you're someone like President Trump, and you. You have people's freedom in your hands. You know, that is one of the incredible powers of the presidency that you have that ability. No matter what someone's accused of, no matter what someone's been convicted of, you can set someone free. And if you have pissed off that person. Yeah. I mean, and especially someone like President Trump. I'm not saying he wouldn't consider the facts. I'm not saying he wouldn't look at the case, obviously in its entirety, but how someone made you feel as a human being is such a huge part of your decision.
B
I thought it was an honest statement, and I thought he put it in, not necessarily in Trump terms. He was almost humble in the way he was saying it.
A
Yeah.
B
This guy hurt my feelings years ago, and I have to be honest, that still sticks with me. He said it in a way that I appreciated, and maybe we're not used to hearing from him.
A
Wouldn't you love to read that letter, though?
B
Yeah. You remember the letter he wrote to the judge? That was. He had a long letter he had written to the judge around his sentencing time as well. I'm sure it's a good one.
A
I'm sure it is, too. But, you know, also, as a human being, when someone writes something to you that's flattering, that's kind, that's humble, that's even reflective, if they want something from you in return for that letter, it just doesn't read the same.
B
But still, people like to be praised and honored and begged for things. People love to have power over others. So we'll see. Man. Glenn, Maxwell and Diddy. My goodness. That's the thing. I think a couple rappers are even asking for pardons. Why not? This is the best shot you got at it. All right, folks, just wanted to hop on, give you that update. You have the morning run. We'll have that up for you here, as always, in a few hours on the feed. And as always as well, top right corner of that Apple podcast app where you see our show page says follow click that button. You can make sure all of our updates come to you. But for now, I'm T.J. holmes. On behalf of my dear Abby Robot. We will talk to y' all soon.
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Podcast Summary: Amy Robach & T.J. Holmes Present – "Overnight: Diddy Just Lost His Trump Card" (Jan 9, 2026)
This episode centers on the dramatic development in Sean "Diddy" Combs' high-profile legal saga: former President Donald Trump has, for the first time, definitively said he is not considering pardoning Diddy. Amy Robach and T.J. Holmes break down what this means for Diddy, analyze the historical context and nuances in Trump’s statements, and discuss the legal avenues still available to Diddy in his efforts to overturn or reduce his prison sentence.
“I was very friendly with him. I got along with him great and seemed like a nice guy. I didn't know him well, but when I ran for office he was very hostile. That is the key point here. So everything was good until 2016.”
The conversation is insightful, conversational, and occasionally irreverent, reflecting on legal strategy, celebrity, politics, and personal dynamics. The hosts blend sharp legal commentary with an understanding of media spectacle and the messiness of real-world relationships.
This episode dissects the end of what many considered Diddy’s most promising route out of prison—a presidential pardon—and illustrates how personal history and political slights can tangibly affect justice at the highest level. If you want to understand the intersection between law, media, and the power of old grudges, this is a must-hear installment.
End of Summary