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Laura Coates Live

Diddy Sentenced To Over Four Years In Prison; Laura Coates Interviews Suge Knight and Sharay Hayes; ICE Agents Raid Chicago's South Shore; Prosecutor Fired By Trump DOJ Leaves Note. Aired 11p-12a ET

Aired October 03, 2025 - 23:00   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.

[23:00:00]

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Thank you so much for watching "NewsNight. Catch our roundtable show, "Table for Five," tomorrow morning. And "Laura Coates Live" starts right now.

LAURA COATES, CNN HOST AND SENIOR LEGAL ANALYST: The closing chapter is written in the downfall of Sean "Diddy" Combs as a judge officially seals his fate. Tonight on "Laura Coates Live."

More than four years in federal prison awaits. That's the reality that Diddy is facing tonight. One of entertainment's biggest stars, an icon of rural music, fashion, and business, sentenced to 50, 5-0, months behind bars. In just a moment, my legal experts and court insiders are going to walk us through the sentencing and what comes next because yes, there is a next.

But today came down to one question: How much time should Diddy serve? Remember, he was convicted of two prostitution-related charges, but he was acquitted of sex trafficking and racketeering, the far more serious crimes that could have landed him life in prison. The prosecution wanted more than 11 years. The defense, 14 months. Basically, time served. The gap could not have been much wider between the two.

And Diddy made one final plea to move the needle in his favor. He addressed the judge directly after a two-month trial where he chose, which was his right, to sit in silence. He told the judge, "I ask your honor for mercy. I beg your honor for mercy. I ask your honor for the chance to be a father again. I ask your honor for the chance to be a son again. No matter what anybody says, I know that I'm truly sorry for it all."

Well, the judge listened, and then he made clear how he saw it. He said a substantial sentence was necessary to send a message that abuse against women must be met with real accountability.

But he also gave Diddy the hope of redemption, saying, "Mr. Combs, you and your family are going to get through this. There's a light at the end of the tunnel. You will have a chance to show your children and the world what real accountability and healing look like. And I'm counting on you to make the most of your second chance."

Those were his final words, the culmination of a very long day in court, a very long process, months in the making.

And the hearing, you know, it lasted nearly seven hours? Atypical. It was tense. It was raw. It was emotional. We heard powerful testimony from Diddy's own family. His six adult children huddled around the podium, telling the court through tears that he is a changed man.

The court also saw about an 11-minute documentary-style video about his family and his cherry work. Diddy actually was overcome and began to sob as that video played.

Five, five of his defense lawyers gave statements. They addressed everything from how prison life has changed him, the long-term impact of his drug addiction. But in the end, they did not get the sentence they wanted. Diddy's team claims it's un-American. And now, they are vowing to appeal, arguing the judge somehow acted as a 13th juror.

(BEGIN VIDEO CLIP)

MARC AGNIFILO, ATTORNEY FOR SEAN "DIDDY" COMBS: The jury reached a verdict on coercion. It found it was not coercion. And I think the judge said coercion today as a basis for a sentence at least a dozen times. We think that that is unconstitutional. We think that a jury verdict should mean more than our jury's verdict seems to mean. And so, we are planning to do it.

(END VIDEO CLIP)

COATES: They were always going to appeal. We begin with CNN's Elizabeth Wagmeister who has been in court since day one. And today, of course, was no exception. My friend, good to see you. What a lengthy day this was. What was Diddy's reaction when the judge handed down his sentence?

ELIZABETH WAGMEISTER, CNN ENTERTAINMENT CORRESPONDENT: You know, as you said, Laura, at certain points throughout this six to seven-hour very lengthy hearing, Diddy was quite emotional. As you said, watching that video, he was crying when he spoke to his mother and kids in the courtroom. He was crying.

[23:04:57] But when the sentence actually came down, not much of a reaction. I've got to tell you, he was quite stoic. When he stood up to leave the courtroom, he did turn to his family. And he made a gesture that, from my observation, made it seem like he was indicating to them it'll all be okay, I love you.

But no cries, no exclamation. You know, nothing that was noticeable from him when the judge said, you are getting more than four years in prison which, of course, we know that he was hoping to walk free today after serving already a year.

COATES: He certainly wanted to. A lot was made of whether he would. Also, a lot made about who would be there present. Cassie Ventura, she was not there, the prosecution's star witness. Jane, the other person who testified as well under a pseudonym, not in the court today.

Their stories, though, they loomed quite large. In fact, Diddy mentioned them specifically in his verbal statement. And, of course, the letter he wrote to the court. The judge told them that he was proud of them for their bravery. Essentially, of coming forward with their story. So, how central was their testimony to the -- the emotions we saw in court today, even from the judge?

WAGMEISTER: You know, you saying that their stories loomed large over the sentencing is perfectly put, Laura. This was really all about them. And when it came to Diddy, in a strange way, the sentencing hearing was almost like a celebration of his life from the defense. You know, they were talking about him as the most moral man to ever live, someone who has inspired so many people, a man who made mistakes but has done so much good for the world.

But when it came to the judge, the judge put the focus on the women. He said that he is proud of Cassie Ventura, that he is proud of Jane. He said that they have touched so many lives of women around the world. He spoke about domestic violence being a huge pervasive problem. He said, this is a problem that happens behind closed doors and them coming forward to tell their truth as credible victims, by the way. Those are the words that the judge used. He said that'll make victims around the world see this doesn't always have to be behind closed doors.

Now, I do want to read you a statement that I received from Cassie Ventura's attorney, Doug Wigdor. He tells me -- quote -- "While nothing can undo the trauma caused by Combs, the sentence imposed today recognizes the impact of the serious offenses he committed. We are confident that with the support of her family and friends, Ms. Ventura will continue healing knowing that her bravery and fortitude have been an inspiration to so many."

And again, the judge was reading some direct quotes from Cassie Ventura's letter that she wrote to him. So, her presence did loom quite large. And it's largely understood that this case would not have even happened. The investigation would not have occurred if she had not come forward with her lawsuit back in November of 2023.

COATES: Or the video that you were responsible for obtaining as well when it comes to that Intercontinental Hotel. Your reporting, precise, nuance and objective. Thank you, Elizabeth Wagmeister.

WAGMEISTER: And thank you, Laura Coates, because I just have to say, covering this trial with you has been such a pleasure. I learned so much from you. And you are the best partner in crime throughout this two-month legal saga.

COATES: Oh, what a sweetheart. Let's not be partners in crime, though. We see what happens.

(LAUGHTER)

Thank you so much.

WAGMEISTER: You're right. I'll be careful.

(LAUGHTER)

COATES: More on the judge's sentencing now with former federal prosecutors Nadia Shihata and Gene Rossi. Nadia was on the prosecution team that convicted R. Kelly in the Eastern District of New York.

Let me begin here with you, Nadia, because the judge tried to thread the needle with this sentence. But because he focused on violence, I wonder what impact that will ultimately have on the appeal that Diddy will have given the fact that violence was a part of the criteria in the sex trafficking, but not for the prostitution-related charges. What do you say?

NADIA SHIHATA, FORMER FEDERAL PROSECUTOR, PROSECUTED R. KELLY: Well, the law, as it stands right now, is very clear that the judge is permitted to consider all sorts of evidence regarding the offense conduct and also relevant conduct and, essentially, the totality of the circumstances.

I think it's clear they are planning to appeal and say he -- it was unconstitutional for him to consider the acquitted conduct. That would, I think, require a change in the current state of the law. So, we'll see where that goes. But I don't think the judge did anything improper in formulating the sentence as he did today.

COATES: The judge actually, Gene, was specific in the courtroom to say, I'm only talking to you about what you've been charged with --

GENE ROSSI, FORMER FEDERAL PROSECUTOR: Sure. Yup.

COATES: -- nonetheless. But he did -- the judge repeatedly cited evidence of Diddy's coercion in his decision. You saw Marc Agnifilo, the lead counsel in this case, pointing that out talking about the so- called acquitted conduct versus what he was actually convicted of. The fact that he can consider these factors is important as is his consideration of the victim impact statements --

[23:10:01]

ROSSI: Sure.

COATES: -- and what they said. Talk to me about that balancing act --

ROSSI: Sure.

COATES: -- the judge came out with.

ROSSI: I just want to supplement what Nadia said, who's just a terrific lawyer. A judge at sentencing, at the federal level especially, has extremely broad discretion. And even though he was acquitted of the sex trafficking and hung jury RICO, he can use relevant conduct for the two convicted counts.

And if you use coercion, force, and violence to commit the two convicted counts to MANN Acts, a judge has full reign to consider that as part of the conviction. For example, if you're charged with tax evasion and you use a firearm to cheat on your taxes, you may not be charged with a gun crime, but you can use that gun conduct to jack up the guidelines.

COATES: Aggravated factors --

ROSSI: Absolutely.

COATES: -- as opposed to mitigating. We talked about that very issue.

ROSSI: Yes.

COATES: Nadia, let me ask you. The sentencing, this was seven hours long. All the lawyers talked. And they provided written statements, of course, in the form of the motions to the court to try to get their suggested sentence.

The one witness who was going to speak backed out because they felt intimidated, it seemed, by the defense's letter, where they were pointing out in the letter something to the effect of that everything that came out of her mouth was a lie and the jury did not believe her. The prosecution equated that with a kind of bullying.

Then there was that 11-minute nostalgic video that they played. I want you to listen for a second to what it said.

(BEGIN VIDEO CLIP)

SEAN "DIDDY" COMBS, RAPPER, RECORD PRODUCER, RECORD EXECUTIVE: I'm telling you right now, you did a great job.

UNKNOWN: Thank you.

COMBS: I'm wrapping my head around meeting you and also telling you that you did a great job at the time.

UNKNOWN: It means a lot.

COMBS: It's a pleasure to meet you.

UNKNOWN: It means a lot. UNKNOWN: (voice-over): I'd rather, at end of the day, be the one standing there with you as the best person. You made us feel the best as a person.

(END VIDEO CLIP)

COATES: That was just a fraction of what we saw. But had you ever seen a criminal defendant at a sentencing put on this kind of a P.R. campaign?

SHIHATA: It's definitely unusual. I'm not sure it was helpful. It was a very kind of slick-produced video. You know, it's -- it's definitely not something I've generally seen. And it was a big juxtaposition between what the judge heard over six weeks of trial about the violent conduct, the coercion, the blackmail, and then this kind of campaign- style video of the Diddy that we all thought we knew before this investigation began. I'm not sure it was helpful, ultimately.

COATES: Gene, the ultimate sentence here, I think people have lot of questions. You did the numbers, you ran the numbers about this.

ROSSI: Ran the numbers.

COATES: He has 50 months, 5-0. What does that really look like in terms of how much time he'll actually serve?

ROSSI: For the victims, I don't have good news. He was sentenced to 50 months. He has served 13. You subtract 15% for good time. He then will serve 26 months in a prison, and then the last six months in a halfway house. So, essentially, he got a 26-month sentence because the six months of the halfway house is -- it's a halfway house.

I do want to say something about that video. When I -- when I heard about it and saw clips of it, I don't want to be prophetic here, but I thought of Charles Dickens, "A Tale of Two Cities."

COATES: Hmm.

ROSSI: This is a tale of two people. I think that video really hurt him because the judge heard the most egregious conduct you'll ever see in a federal courtroom in his lifetime. And then they have a video that shows something slick. I don't think it moved the needle in their favor.

COATES: Well, the judge essentially said that all can be true and you still have to be held accountable for what was actually convicted. Nadia Shihata, Gene Rossi, thank you both.

ROSSI: Thank you.

COATES: One of the moments that stunned the courtroom today was the fact that Diddy, apparently, had booked, according to the prosecution, had booked a speaking event for next week. The height of hubris is how prosecutors put it. But the defense clarified it was going to be a chance for Diddy to hold a teaching engagement to help others convicted of crimes. 50cent, who no fan of Diddy, wasted no time mocking him for it, saying

-- quote -- "Hey, to whoever was booking Diddy for speaking engagement, I heard he won't be able to make it. I'm available."

Joining me now, Rob Shuter, Diddy's former publicist, also Kierna Mayo, former editor-in-chief of Ebony Magazine and columnist at "Hammer & Hope." Welcome to you both.

Rob, let me begin with you here. You were his former publicist. What did you make of Diddy potentially thinking that he might be free to schedule something next week and just the whole -- the whole spectacle that followed from that very accusation?

ROB SHUTER, SEAN "DIDDY" COMBS'S FORMER PUBLICIST: Yeah, I think I was the first to report that he felt really, really confident about what was going to happen today.

[23:15:00]

We found out during the morning that there were some engagements next week, a little unclear exactly what they are.

COATES: Uh-hmm.

SHUTER: But I, too, reported that he had a private plane waiting for him here in New York to get him to Miami. They thought they entered that court this morning really, really confident. And as the day went on, they became less and less confident. Although I've got to say, once that final sentence was handed down, I still think this is a big win for Puff. He will see it that way, too.

Four years. It's a long time, but it's not a lifetime. Diddy will have another chapter. He will emerge from jail. He's still a very wealthy, very powerful man. And so, I'm sure he will be spending the next two, three, four years planning what he is going to do next.

COATES: I mean, the judge, Kierna, pointed out his resources find him half a million dollars, talked about the ability to engage this behavior for so long because of the network of resources as well.

And they have that video that played about 11 minutes or so. His young children featured in it as well, grownups at this point in time, who's talked about through tears, not wanting to be fatherless. Four of them have already lost their mother, Kim Porter.

But the video highlighted his rise from adversity to what he perceived as the pinnacle of the music world. I want to play for the audience a little bit more of what the judge saw.

(BEGIN VIDEO CLIP)

COMBS: So instead of talking about the guns and the violence, I was always talking about a better life, places we didn't go before, things we never wore, cars we never drove, houses we never lived in. Then I brought an aspiration to hip-hop, tried to take it out of just being street. Our whole stuff was a fantasy and a dream, a dream that I always felt would come true.

(END VIDEO CLIP)

COATES: How much does Diddy still believe in that image of himself?

SHUTER: I think Diddy --

KIERNA MAYO, COLUMNIST AT "HAMMER & HOPE," FORMER EDITOR-IN-CHIEF OF EBONY MAGAZINE: Say again, Laura.

COATES: Kierna, let me ask you about that image that he wants to portray to that judge and how he views himself. Can you contextualize how he sees himself based on your experience?

MAYO: Yeah, I mean, there's a lot of hubris. I'm sorry to say it really does smack of like Diddy-ism. It's pretty classic, like he's just on stage. I'm -- I'm surprised that that's the tactic that they took.

But, look, Laura, you know, I always think of these things not in legal terms but in social and cultural terms in the ways that it really hits human beings and how we live our lives. And I'm just thinking about the takeaway.

I'm really proud that the judge kind of resisted the allure of wealth and fame and power and all that Diddy really still embodies and will always embody because in the end, you know, Cassie and all victims are just deserving of so much more, like the attention should remain on them.

And while I admit -- I admittedly just feel really empathetic toward his children. You know, I -- I looked at the list of people who wrote letters on his behalf. I knew many of them. Like people loved this man. He's someone's father and friend, right?

But -- but so are his many victims. Just on a karmic level because, again, I'm completely not taking this from a legal place. But we understand that Diddy has caused harm. And in some respect, having to pay for causing harm just makes sense. It does.

COATES: The court mentioned the word irreparable harm that was caused to the two women who were named in the actual indictment of the convicted charges. Rob, I mean, the judge told Diddy -- quote -- "I'm counting on you to make the most of your second chance." What does that look like? What is the second chance for somebody like Diddy, particularly in the music industry and the entertainment space that Kierna was speaking of? What does that look like for him?

SHUTER: For Puff, it looks like a comeback. He won't be satisfied until he's back on top. I'm not sure he'll feel it internally, but externally, he now is going to be driven to have a number one album. He wants to sell out Madison Square Garden. I think his lawyer confirmed my reporting that he wanted to do that. He's going to go on tour. I hope along the way, though, too.

He is a very smart person, and he can smell sense, change in what is going on in the world, and I'm sure there will be some sort of charity aspect that he sets up, too. Once again, will his heart desire that? I'm not sure.

COATES: Hmm.

SHUTER: But will he want that for his fans and for himself? He desperately, desperately loved being Diddy. I worked for a lot of celebrities. Nobody liked being a star more than him. He liked going to the best restaurants.

[23:20:00]

He liked sitting front row at all the fashion shows. He loved going to the Met ball. We watched the Met ball. They love him there. So, Puffy is going to fight, fight really hard to get back on top.

COATES: Kierna, you simply agree. I see your head quickly. You want to comment?

MAYO: Yeah, completely. I can't imagine that he will stop. You know, he's the king of can't stop, won't stop. So, I do fully expect that when he returns, he will try his best to make uh waves in the world again. I'm just hoping that -- you know, in the same way that he will now have to pay this $500,000 --

COATES: Yeah.

MAYO: -- fee but -- essentially back to the government, I'm hoping that he will align himself with some -- lot more righteous causes, like the next $500,000 should perhaps go to some folks in Chicago who need defense against ICE right now.

COATES: We'll see.

MAYO: You know, there are real things happening in the world, and we need people to use their power in the right way.

COATES: Rob Shuter, Kierna Mayo, thank you both so much. Still ahead tonight, Suge Knight calls in from prison with his first reaction to Diddy's sentence and his message to his one-time rival.

(COMMERCIAL BREAK)

[23:25:00]

(COMMERCIAL BREAK)

COATES: Diddy is facing some serious time behind bars. So, what could he be facing in prison over the next three or so years? There's one man who might know better than anybody else. Diddy's one-time nemesis and founder of Death Row Records, Suge Knight. I talked to him earlier tonight on the phone from prison.

(BEGIN VIDEOTAPE)

COATES: Suge, we've talked a lot throughout the course of this trial. He got four years, two months. Do you agree with the sentence?

SUGE KNIGHT, FOUNDER, OF DEATH ROW RECORDS (via telephone): Well, I'm not the judge or the jury, but what I would say is that on one side of it, it's great for his children because kids are the future. And on the other side of it, these two victims got some satisfaction out of it.

But when you really look at it, three years seems like 30 years to Puffy. So, it's not like he walking in there and it's going to be Disneyland. You know, we have a reputation, and he's a famous person. So, either people are going to love him or they are going to hate him. It's not going to be a gray area. So, I'm quite sure there's a lot, a lot, a lot of controversy going on, you know?

COATES: Well, you know his defense counsel raised that point to the judge and said something like for someone like him, it'd be a trophy to hurt him. He already said that, apparently, he was almost attacked, shanked in jail. What's the next three and a half, four years going to be like for him?

KNIGHT (via telephone): Well, more than likely, they're going to try to do their best to protect him. But what we all got to understand is that we do understand what we signed up for. And we do understand that we benefit from mostly everything we do.

So, when you're big, get a little rough. You got to -- you got to respect him and lay in him (ph). And he can get his laces ready (ph) with God or he can get his workout -- workout on and get ready to protect himself. One way or the other. It's going to be a situation that's not pleasant. I'm happy (ph) for him, you know?

COATES: Suge, I mean, he said today, I know that I've learned my lesson. He has been arguing that he's a changed man who can, wants to do better, wanted the second chance to have immediate freedom. Do you believe him?

KNIGHT (via telephone): Well, what I believe is that -- the only thing I felt that they didn't do, none of his baby mothers came in and spoke up and said they'd never been beaten. They never had anything done to them badly. So that's a question. Okay, I think that's one of the things that the prosecution didn't ever look at.

COATES: Suge, if you could tell Diddy one thing tonight, what would it be?

KNIGHT (via telephone): Well, I've really got a relationship with God. So, I don't need to tell him that. But if it was about surviving in prison, don't listen to nobody in prison. Go there and do your own time. First thing you do, don't worry about who got your back. Have your own back. And use your time to better yourself. Use your time to working out, getting your health better, you know.

Don't get on drugs because you know there's more drugs in prison than there is in the streets. So, you got to stay away from the drugs, stay away from the unnecessary B.S., and make sure you make it home safely. But you're not home until you're home. Be prepared to fight. COATES: Suge Knight, thank you.

KNIGHT (via telephone): Thank you so much. Have a good night.

(END VIDEOTAPE)

COATES: You know, my next guest is one of the key witnesses during the trial's early days. Sharay "The Punisher" Hayes, an exotic dancer, who testified about the freak-offs he participated in with Cassie in the presence of Diddy. And Sharay joins me now. He's also the author of "In Search of Freezer Meat." Sharay, you actually went to the courthouse today to see this case through. Do you agree with the sentence?

SHARAY "THE PUNISHER" HAYES, EXOTIC DANCER WHO TESTIFIED AT DIDDY TRIAL: Um, I'm ambivalent. You know, I -- honestly, when I went down there, I was assuming time served. But that was pretty much just based on the precedents and other case law that I actually looked into. But there is a space where the judge -- he had to consider the victims, and he considered the behavior while Mr. Combs were being investigated. So, a slap on the wrist of time served would have been kind of in just to the -- the victims.

[23:29:58]

But, um, it's just hard when you, like I guess the defense is saying, you hear coercion as a catalyst for his sentence and it was something he was acquitted of. So, it's kind of a gray area, you know?

COATES: When we last spoke, you talked to me about your testimony weighing on you because of the impact it could have on the case and the idea of coercion, particularly with Cassie Ventura, which you say was not the experience that you had or perceived in spite of what she has now said. How are you feeling about that now that Diddy has been sentenced?

HAYES: Um, so, you know, after the fact, I started to realize that my testimony was really impactful, whereas some people say I might have been considered something as the swing witness because I --

COATES: Hmm.

HAYES: -- I kind of countered what the prosecution was trying to allege with consent. So, I'm seeing it all the way through, knowing that his acquittals, I could have been a source of that. And then --

COATES: Hmm.

HAYES: -- the judge still believing from what he heard that coercion exists. Um, again, it's kind of like a gray area to be that impactful in a way where there may still be victims, but my testimony might have stopped justice from being fully gained.

COATES: Well, you know, the jury made their own minds up. They were the 12 who decided this case based on the whole span of the trial. There was a moment today when Diddy was speaking to the court. He said that he was sick, sick from the drugs. He was out of control. You heard him speak today. How did he compare to the man you interacted with? Did you see a different person?

HAYES: Um, you know, hearing him actually speak in person, I have to honestly say I was -- I was moved.

COATES: Hmm.

HAYES: It made me sad. You know, it made sad because growing up as a young Black man, he's -- I have to say he is an idol. He's somebody that I look up to. You know, that type of success from somebody from my neighborhood is not something you see a lot as a young Black man.

So, seeing him in his lowest point and struggling that way, fighting for his life, and I'm not trying to take away from any of the heinous behavior, the negativity, but it did -- I did have empathy for that moment and him just, you know, acknowledging everything.

And if it was, in fact, the drugs, that out of control behavior with this type of fall, it's unfortunate to see, you know, somebody create that type of success squander it in this type of way.

COATES: He himself said something similar. Sharay Hayes, thank you.

HAYES: Thank you, Laura.

COATES: A reminder, you can revisit the ups and the downs of this entire case on my podcast, "Trial by Jury," available wherever you get your podcast.

Still ahead tonight, the dramatic helicopter-involved ICE raid in Chicago that has hit quite a nerve after American citizens were reportedly pulled out of their homes in the dark of the night. Details next.

(COMMERCIAL BREAK)

[23:35:00]

(COMMERCIAL BREAK)

COATES: In the darkness of the night, immigration enforcement agents pulling adults and children from their apartments in Chicago's South Shore neighborhood.

Daryl Ballard (ph), who lives in the building next door to where the raid happened, capturing video of the operation showing agents swarming the apartment building.

You can hear a helicopter hovering above, which Ballard (ph) identifies as a Black Hawk helicopter. The Department of Homeland Security confirming the raid led to the arrest of 37 undocumented immigrants, mostly from Venezuela, but also people from Colombia and Mexico and Nigeria. Residents and neighbors telling CNN affiliate WLS that the operation left them all but shaken.

(BEGIN VIDEO CLIP)

UNKNOWN: They just treated us like we were nothing. It was scary because I've never had a gun put in my face.

UNKNOWN: We're in the siege. We're being invaded by our own military.

UNKNOWN: It was terrifying. The kids were crying. People were screaming. They looked very distraught. I was out there crying when I've seen a little girl come around the corner. They were bringing the kids out, too. Had them zip-tied to each other. That's all I kept asking. Where's the morality? Where's the human? One of them literally laughed. He was standing right here. He said, (bleep) kids.

(END VIDEO CLIP)

COATES: With me now, former deputy and special assistant to President Biden, Dan Koh, and CNN political commentator Shermichael Singleton. I mean, Shermichael, this is clearly an escalation from what we have seen before in different raids. How has this operation unfolded? Why is this the tactic, you think, that might be used? Will it be sustainable?

SHERMICHAEL SINGLETON, CNN POLITICAL COMMENTATOR, REPUBLICAN STRATEGIST: Well, I think they want the element of surprise. I understand that your prosecutor raids do occur, but I do think you politically have to be careful with the optics. I mean, this is just a matter of politics. If people are going to see this, I can see easily how many people would be uncomfortable.

Again, I get you want the element of surprise, you don't want people to get away, you don't want criminals either way. I think we could all agree with that. If there's a way to be clear what doors to knock on so that you're not -- so that you don't run into unintended consequences, right? You don't want to be arresting or handcuffing people who are Americans, who are sleeping in their beds.

And so, if there's a way to avoid that, I would probably try my best to figure out the best way to do this so that you're not causing unnecessary harm and strife to innocent Americans who are simply sleeping.

COATES: I mean, Dan, this discussion about whether the end justifies the means, there is -- DHS says at least one -- at least one U.S. citizen with an active narcotics warrant was arrested and turned over to local law enforcement.

[23:40:06]

As Shermichael points out, there was also details about Americans who were swept up in this actual net as well. But on the idea of the end justifying the means, will that be enough to placate people who are totally offended and horrified by the optics?

DAN KOH, FORMER WHITE HOUSE SENIOR AIDE TO PRESIDENT JOE BIDEN: No. I think this is a horrific testament to the America that we're living in, and candidly, what people feared about a Donald Trump presidency, and that frustrates people when they say and are being gaslighted now to not use hyperbolic language about this president.

We were told first that only violent criminals would fall under this umbrella. Now, we're seeing a guy, Roderick Johnson, a 67-year-old American, who had his door knocked down, was detained for three hours. He asked for a lawyer. They wouldn't give him one. They asked for a warrant. He wouldn't them him one.

So, there has been so much history, and I don't have to tell either of you at this table, of tension between law enforcement and citizens for so long, progress that has been made. And when this happens, when mass men are knocking down doors and detaining American citizens, that sets us back as a country. And it is so damaging. And it just continues to manifest on itself. That feeds this narrative about Donald Trump for people who are skeptical of him.

COATES: Let me focus on that tension for a second because there was this -- you've heard about the ICEBlock, the app that is essentially around that showed where they were and how to identify their location. We know, of course, that this has now been removed, and there is a lot of controversy around the removal of it.

Um, when you look at that tension with Silicon Valley, with apps, social media, and Apple about this very notion, does the application of the identifying and locating of ICE agents, does that pose enough of a security threat to ICE agents to warrant the removal of the app?

SINGLETON: Oh, I certainly think so. I mean, look at what happened in Dallas a week ago. Allegedly, the perpetrator of the crime there used that app to target ICE agents. Again, you asked a question, does end justify the means? I think for most people, they will say, look, we want people who are here legally removed, we want people who have committed heinous crimes removed.

And I think you have to have this delicate balance of not sort of disrupting the normal ecosystem of regular American citizens while also removing people who should not be here. You're going to get a lot of support from people when you're doing that. But when you have those unintended consequences, when you're kicking down the doors of regular people, that's when the lines get blurred.

And so, again, my advice would be do the job. People want them removed. You're going to get the support there. But let's just be careful that we're not, I guess, harming people, if you will, who should not be harmed in the process of us trying to remove people who are in the country illegally.

COATES: Why that place, why that way will be a pervasive question, as it should be, particularly given the campaign promises about most violent firsts. You have to wonder whether this net actually captured those very people. But you have this split screen, the government working in that capacity, and then shut down the block about things. Then when you look at that split screen, what is that suggest for the voters of this country?

KOH: I think it's incredibly distressing. Let me give you a couple examples. For many people, it was once again the tech CEOs, not for people but just bending the knee of the president. This whole conversation about money and the budget. We have $50 billion a year that go to oil subsidies when they're having record profits. We have $50 billion going to pharma. We have people able to write off their private jets and their yachts.

COATES: Uh-hmm.

KOH: Yet we're having a raging debate about 0.4% of the Medicaid budget that will allow hospitals to not I.D. people before deciding whether to let a gunshot wound victim bleed out, or a mother who's having complications delivering a child to deliver their baby, or somebody who is in a car crash to be able to get medical care.

So, when people are seeing that, I think they're just blaming both sides. They're saying, no one is working for me. A New York Times poll about who's more at fault had 26% Republicans, 19% Democrats, 33% blaming both.

COATES: Uh-hmm.

KOH: The rest of them having no idea who to blame because they're just so disaffected by this. They're seeing tech companies bend, they're seeing all of these handouts to the big guys, and they're getting screwed.

SINGLETON: But you know what? If Democrats were to say, let's keep the government open and compromise on this, the president, John Thune, the speaker of the House, Mike Johnson, have all signaled that they're willing to compromise on healthcare.

And so, I understand why Democrats are taking the position that they're taking. I don't agree with it, but I understand. But you're going to inadvertently impact so many people who rely on an open government. Let's keep it open, Dan, and let's do what we're doing. Have the conversation and try to compromise where possible on healthcare.

COATES: You both seem to be operating in good faith. That's not the trust issue we're facing on Capitol Hill.

[23:44:53]

KOH: I think when there are clear racist tropes videos being made and J.D. Vance, who was supposed to be setting an example for our children, gets up there, laughs it off and says, well, Hakeem Jeffries is not Latino, so he shouldn't be offended, every single person of color who has ever seen something like that understands the pain of those kind of videos. And right now, Donald Trump and MAGA are just writing it off as a joke. That is so offensive to so many Americans.

COATES: I think there are a number of federal employees who don't see anything funny about the predicament they might find themselves in and how. Dan, Shermichael, thank you both.

KOH: Thanks, Laura.

SINGLETON: Thank you.

COATES: If anyone had any doubts about the purge happening at Trump's DOJ, well, then you just wait till you read this letter from the 20- year career prosecutor who was just fired. I'll show you next.

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COATES: Tonight, a fired federal prosecutor taping a note about duty to the door on his way out.

[23:49:57]

Michael Ben'Ary, who was leading the only criminal prosecution on U.S. soil against a man allegedly involved in the planning of a bombing during the U.S. withdrawal from Afghanistan in 2021, taking issue with the dismissal of multiple career officials in the DOJ in just recent months, writing to colleagues, "The political leadership of the department have violated the principles of the Constitution, jeopardizing our national security and making American citizens less safe."

I want to bring in former federal prosecutor, Mike Gordon, who handled some of the most high-profile cases against January 6 rioters and is suing the administration over his firing this summer, arguing that the decision was politically-motivated.

Mike, welcome. Eager to get your perspective on the times we're in. Ben'Ary parting messaging to his colleagues included a plea to continue to do the right thing. What do you make of him not going out quietly? And will other rank-and-file and line prosecutors follow suit?

MIKE GORDON, FORMER FEDERAL PROSECUTOR: Thanks, Laura, first of all, for having me on. And I have to say, I am so proud of people like Michael Ben'Ary for speaking out and calling out what is happening in this country and to the Department of Justice.

Unfortunately, letters like this have become incredibly common. I've read them from colleagues every week from the past few months as prosecutor after prosecutor and FBI agent after FBI agent has been unfairly fired.

COATES: You know, one of the things he wrote about was that "This highlights the most troubling aspect of the current operation of the Department of Justice. The leadership is more concerned with punishing the president's perceived enemies than they are with protecting our national security" -- unquote.

Tell me, what are the implications of firings like this person, Ben'Ary, for national security, particularly given the cases that he was assigned to oversee? Will our national security and the prosecution of cases like that be compromised?

GORDON: Yes. So, let's talk about how the government is organized. There are 93 U.S. attorney's offices, they're all over the country, and they deal with the crimes that happen in their areas. The Eastern District of Virginia, where Michael Ben'Ary worked, because of where it sits, is the office that handles most or the most important terrorism cases in this country.

And by firing Ben'Ary, who was the chief of the National Security Section, after just forcing the resignation of the deputy chief of the National Security Section the week before over the Jim Comey indictment, and after demoting the chief cybercrime prosecutor, Maya Song, who was the first assistant in the office, what this administration has done is they have decapitated the national security prosecution capacity of the most important U.S. attorney's office in the country for dealing with terrorism, and they did all of that just based on some unfounded, inaccurate social media posts.

So, random people on social media appear to be staffing the Department of Justice's most important counterterrorism units. That should scare everyone.

COATES: You know, the Eastern District of Virginia, while not getting all the attention of, say, the SDNY in the everyday conversations about prosecutions and high-profile matters in the press, is a storied institution in and of itself for the reasons that you have described.

The person who now heads that office does not have prosecution experience, overseeing attorneys, career prosecutors with a tremendous amount and who must be suffering from at least an impact on the morale given what you have displayed. Is she in over her head?

GORDON: I don't know U.S. Attorney Halligan personally. I've never met her. But no one with the background that she has or the lack of background that she has should be in the position she's in. Running any U.S. attorney's office, but particularly someplace like the Eastern District of Virginia, requires not only having criminal expertise, but also civil and appellate. She has none of the above.

These are the most serious matters facing our country. And we need people in those positions who have extensive experience, ideally decades of experience, handling these cases, people like Michael Ben- Ary with 20 years of experience, someone who was the chief of staff at DEA, somebody who was national security and other types of serious cases like that. I don't know Ms. Halligan, but I can't imagine choosing her for this role.

[23:55:00]

COATES: Mike, quickly, it must be enticing to want to leave given what's happening. How do prosecutors balance the resolve to stay in their commitment and wanting to leave?

GORDON: I tell you, I've had that conversation. When I was in DOJ, I've had it with so many colleagues, and I've had it since then. People are torn between on one hand feeling like if they stay, are they complicit in the political leadership destroying the Department of Justice day by day as they're doing, or are they better off staying and doing their best to continue the department's mission of following the facts and the law wherever it leads without fear or favor? People don't know what to do, but they also have mortgages and families to feed and, you know, their own concerns. So, it's tough across the department.

COATES: A horrible choice to make for public servants. Mike Gordon, thank you for coming.

GORDON: Thank you for having me.

COATES: And thank all of you for watching. "Anderson Cooper 360" is next.

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