Loading summary
Michael Popak
Every day, the Department of Justice under Donald Trump finds a new way to screw up in court. It's certainly a function of the fact there's a brain drain. People are quitting because their ethics are being compromised and they won't stand for it any longer. That has hollowed out the Department of Justice and all of its offices, and the remaining people are overworked and underpaid. And then you have errors like what just happened this week in New York, where lawyers in the Southern District of New York prosecutor's office representing the Department of Transportation filed on the public filing for all to see an internal memo of attorney client privilege recommendations to the Department of Transportation about the very case. In other words, they accidentally, inadvertently, but maybe on purpose uploaded to the public filing a document that represents their playbook, in which they say in it, because we've all seen it now, that the judge will never buy this series of arguments. We've got to stop making them. And we're going to have to start making these new arguments. You know, it's interesting, but certainly not something the public should see, the judge should see, or the other side should see. And now we've got open warfare between one part of the government under Trump and another part where the Department of Transportation, as the client, is attacking publicly their lawyers as committing professional malpractice and even suggesting without any evidence whatsoever. But that never stopped the Trump administration before even suggesting that the lawyers in New York are trying to sabotage the Trump administration. Oh, I'm going to break it down for you right here on the Midas Dutch Network. I'm Michael Popach. Let's dive in. This was a little followed case. I followed it because I lived in New York. But it has to do with the congestion, toll pricing being charged by the state to try to reduce the amount of traffic in New York. It's a good thing, trust me. And it's working. The $9 toll that's being charged for anybody who enters the city below 60th street, if you want to get specific, has reduced the car population by 12%. That's a lot. Like 12 million less cars are coming in. That's a lot. But to the Trump administration and to Donald Trump, who wants to be the king of New York, he wants to get rid of it. So he had his transportation secretary, Sean Duffy, Remember, he used to be on the Real World, who's married to Rachel Campos Duffy, Fox News, who used to be on the Real World. That's his qualifications to be our transportation secretary. So he's fighting for the Trump administration against New York. All right, it was a case that was filed like in February. We covered it here on Midas Dutch illegal af. What happened? Well, what should have been a routine filing by the lawyers representing the Department of Transportation in the Southern District of New York's office turned into this major screw up. They uploaded what they thought was a letter addressed to Judge Lyman telling him about a procedural issue and instead they uploaded a letter internal dated 11 April from the three lawyers on the case. I'm not going to name them even though they've been out already. I think they've, they've suffered enough to, to address to Aaron Hendrickson, senior trial attorney in the U.S. department of Transportation, basically the lead lawyer for the client, telling her we're basically, this is a losing argument that you're making to Judge Lyman. He's going to reject it. Don't argue that it's illegal to have inserted the new toll in. That's a loser. You should go this way. You know what lawyers normally do. Lawyers will hope good lawyers will be candid with their client and say this is a losing strategy. But here's a different or better way that may be successful. Now, what good lawyers don't usually do unless they're completely gassed and inexperienced is upload to the, to the public docket the actual attorney client memo, pardon me, that they've sent to their client. And it was up there for quite some time. I mean, many, many, many commentators, including the legal AF and surrounding Midas Touch all grabbed ahold of it. I got a copy of it. Now, the judge has subsequently sealed it, so I'm not going to read from actual parts of it. But I will tell you in general, it says things like Judge Lyman won't go for this. Judge Lyman has rejected this. This is a loser. Try this route. Now what you would. Can I tell you how things like this happen as a practitioner? They happen. I mean, there are rules already on the books that if there is an inadvertent disclosure of an attorney client document and you find it out in a reasonable amount of time, you can demand its return, you can demand its destruction, you can claw it back. It's because we have so many pieces of paper now in the law, terabytes of information can be exchanged in a case and something can slip through the cracks. It happens. It's human error. Doesn't matter how much AI you use or how much or how many, how much investment you make in a platform to review the documents. It's going to happen. Now this One, I know how it happened because on the. It used to be back in old timey times, when I started my career, you would literally have to go down to court and have a courier or somebody in your office file it in person here and you get a stamp, okay? And that was really through the 90s, around early 2000s, we went to an electronic docket so that everything was. You would, you would upload it from your computer. See the problem? You have to hit the right document, attach the right document, like you're attaching a document to an email and upload it to the system. And then you double check to make sure it's right. And then the clerk's office double checks to make sure it's right. If your eye slips for a minute and you accidentally attach the wrong document, because these two documents sort of look the same because they're on letterhead, the dates are different, but maybe when you're double checking that little tiny version of it, you missed it. Then you upload your private memo instead of the correspondence to the judge. They immediately. It happens. So it can happen. You know, I'll be frank. I mean, on my trial team, in my life in 35 years, we've accidentally provided the other side with an attorney client document, immediately figured it out and clawed it back. It's happened to everybody. If it hasn't happened to you, it's because you're not handling big enough cases. That's all. So when they figured it out, while the Transportation Department is busy bashing, their first reaction wasn't, let's join together and fix this. You know, this is a bad thing, but we can fix this. You know, sort of circle the wagons, hold hands, attorney client. No. They immediately started bashing their own lawyers in public. It's professional malpractice. They should be fired. This is the transfer. This is the one side of the Trump administration against the other side of the Trump administration. Open warfare. They actually said out loud, some, some spokesperson for the transportation side actually questioned whether they did it on purpose as part of the resistance. Now, it probably didn't help that one of the three lawyers who signed this, who's the, the deputy chief, if you go on her LinkedIn, she has reposted some things that are not, that are a little bit of, a little bit critical to the Trump administration. But I don't think that led her to violate her professional ethics and to, and to risk her bar license by uploading a document that shouldn't have been in order to tank the case. I just don't Think that. I'm sorry, I think better of people in my profession. Now, what they did immediately, within 20 minutes after the media found it and everybody's phone blew up, here's what they filed. Let me read it to you. This office represents defendant Sean Duffy, Secretary of Transportation and the DOT and all that we write respectfully to request the court remove or permanently seal docket entry 65, which is an attorney client privilege, attorney work product communication inadvertently filed on the docket in this matter last night at 9:04 last night. Oh, actually they waited almost, almost a full day to do this. At 9:04pm last night, undersigned counsel inadvertently uploaded an attorney client communication from this office to the Department of Transportation through the docket rather than a letter intended for your honor. Immediately upon realizing this etter at 9:18pm we contacted all council of record via email and asked them to not to download it or to delete it. We then took the steps with the clerk's office. And we understand that at 9:48pm the prior night, the clerk's office had put a temporary seal on the document and it was no longer available on the docket. Actually, it was available because I got a copy of it. Although the contents of the document have been made public in news reporting, the document has been filed in error and should not be considered part of the court docket. The judge subsequently sealed it again. So I'm going to be respectful and not read from actual parts of it. I gave you the gist though. And then they asked the court to seal it. They say it's a mistake, it was done in error. It wasn't done on purpose. We shouldn't discuss it any longer. And then it's signed by the three, the three lawyers who are now in the doghouse because the new reporting is in response. The Department of Justice haven't fired these lawyers yet, but it's coming. They've transferred them off the case and they've sent the case to Washington to be run by, I guess, Pam Bondi's hand selected team out of Washington. We call that Main Justice. And then it was signed by Jay Clayton in that office. Now let me talk about Jay Clayton in that office for a minute. That office is racked with strife right now. It is. It was one of the most elite U.S. attorney's offices in the country. If you wanted to become a U.S. attorney, and I did at one point in my career, early on, it's, it is the, it is the job. Insert your favorite sport champion team. You know, like the New York Yankees or Lakers or whatever. It is the apex. It's where you want to work. And it has suffered a tremendous brain drain ever since Trump came in, because nobody wants to work in the Trump administration, especially what they did with the Mayor Adams indictment. After the Mayor Adams indictment was forced to be dismissed, there's like 10 different lawyers that quit in the Manhattan DA's office at senior level, including the acting interim U.S. attorney, Danielle Sassoon. And they wrote letters about it that we've all seen. So people that are left, there's very few people that are left that are senior know what they're doing. You know, they've. The senior people that knew what they're doing, that were the stars have all gotten out. That means the people that are remaining, I'm not saying they're not stars, but they're exhausted and they're doing the work of like two times that amount of people, you know, and errors happen like that when you press and you pressure an organization. They don't even have a U.S. attorney. They have an acting U.S. attorney in Jay Clayton that they list them as the U.S. attorney. He's not the U.S. attorney, he's the acting U.S. attorney because he hasn't been confirmed. And so, you know, and then you have the Transport Department of Transportation, they send out a press release or a statement that says, oh, this just shows the continued decline of A once proud U.S. attorney's office in the Southern District. I mean, they try to use anything for political expediency. I feel sorry for these three lawyers. I don't think they did it on purpose. I don't have any insider knowledge. I just don't think they would have done that. I've seen errors like this happen before. It does happen before. But what doesn't happen is what I'm reporting on is that the. Your client doesn't go to the press immediately and bash you and accuse you of committing malpractice and saying that you're playing for the other side. That doesn't happen. And that's the hot take here. So we're glad you're here on Midas Touch. Hit the subscribe button for Midas Touch and then come on over to the Legal AF YouTube channel, Legal AFMTN. We do it parallel in collaboration with Midas Touch. We're continuing to grow that It's. We're adding 70,000, 80,000 subscribers a month. Be the next one, get reminders there. We're doing a dozen videos a day. Some amazing contributors over there, including some brand new ones like Dave Aronberg and Melba Pearson, and we're adding Sidney Blumenthal and Sean Wallentz, Professor Wilentz out of Princeton, all coming together to bring you the highest quality yet entertaining information at the intersection of law and politics. So until My next Legal AF podcast or my next Legal AF the YouTube channel, this is Michael Popak and I'm reporting in collaboration with the Midas Touch Network. We just launched the Legal AF YouTube channel. Help us build this pro democracy channel where I'll be curating the top stories the intersection of law and politics. Go to YouTube now and free subscribe at legal a FMTN. That's at legal AFMTN.
ShipStation Ad
If you're running a retail business, don't let disorganized order fulfillment cause chaos. Use Shipstation instead. From running a business out of your garage to multiple warehouses, shipstation is ideal for every phase of your your growth. Save time with one login for all your stores and by automating tasks. Plus, you'll get the best shipping rates from global carriers. Calm the chaos with the shipping software that delivers. Start a free trial at shipstation. Com audio. That's ShipStation. Com Audio.
Title: Trump DOJ Accidentally Confesses It Lied to Judge
Release Date: April 25, 2025
Hosts: Ben Meiselas, Michael Popok, Karen Friedman Agnifilo
Executive Producer: Meidas Media Network
In this gripping episode of Legal AF by MeidasTouch, host Michael Popok delves into a significant mishap within the Department of Justice (DOJ) during the Trump administration. The episode, released on April 25, 2025, provides an in-depth analysis of how the DOJ inadvertently exposed its internal strategies in a high-stakes legal battle against New York's Department of Transportation (DOT).
Michael Popok opens the discussion by highlighting the systemic issues plaguing the DOJ under President Donald Trump. He states:
"Every day, the Department of Justice under Donald Trump finds a new way to screw up in court." [00:00]
Popok attributes these mistakes to a significant "brain drain" within the department, caused by ethical compromises that have led many professionals to resign. This exodus has left the DOJ's remaining staff "overworked and underpaid," exacerbating the likelihood of errors.
The focal point of the episode is a recent blunder by DOJ lawyers in the Southern District of New York. These lawyers, representing the DOT, inadvertently filed an internal memo detailing attorney-client privilege recommendations into the public court docket. Popok elaborates:
"They accidentally, inadvertently, but maybe on purpose uploaded to the public filing a document that represents their playbook..." [03:45]
This memo explicitly outlined that the current legal arguments against New York's congestion tolls were weak and likely to be dismissed by Judge Lyman. The disclosure of such internal strategies is unprecedented and paints the DOJ's legal tactics in a compromising light.
Popok provides context about the case itself, emphasizing its significance:
"The $9 toll that's being charged for anybody who enters the city below 60th street... has reduced the car population by 12%." [05:30]
Implemented to alleviate traffic congestion, the toll has successfully decreased vehicular influx by 12 million cars. However, the Trump administration, under the leadership of Transportation Secretary Sean Duffy, seeks to abolish these tolls, positioning themselves against effective public policy.
Explaining how the error occurred, Popok draws from his extensive legal experience:
"You have to hit the right document, like you're attaching a document to an email... and then you double check to make sure it's right. And then the clerk's office double checks to make sure it's right. If your eye slips for a minute..." [09:15]
The transition to electronic filings increased the risk of such mistakes. Despite safeguards, the complexity and volume of digital documents make human error inevitable. Popok reassures listeners that such mistakes are "human error" and not indicative of deliberate wrongdoing.
Instead of collaboratively addressing the mistake, the DOJ's Department of Transportation publicly criticized their own lawyers, accusing them of "professional malpractice" and suggesting motives of sabotage:
"They immediately started bashing their own lawyers in public." [11:05]
This reaction reflects deep-seated tensions within the Trump administration's factions of the DOJ. Popok refers to this as "open warfare" between different branches of the government under Trump.
The Southern District of New York's U.S. Attorney's office has been severely affected by staff turnover, with numerous senior lawyers resigning over ethical concerns, particularly after the controversial dismissal of the Mayor Adams indictment. Popok notes:
"The senior people that knew what they're doing, that were the stars have all gotten out... errors happen like that when you press and you pressure an organization." [10:45]
This depletion of experienced personnel has left the office "exhausted and... doing the work of like two times that amount of people," increasing the likelihood of further missteps.
Popok underscores the rarity of a client publicly denouncing their own lawyers following an accidental disclosure:
"What doesn't happen is... the Department of Transportation bashes their own lawyers." [12:30]
He expresses sympathy for the involved lawyers, asserting that such errors, while serious, are not typically intentional or ethically driven.
Wrapping up, Popok reflects on the broader implications of this incident for the DOJ and the integrity of legal proceedings under the Trump administration. He emphasizes the need for accountability and the restoration of ethical standards within the department to prevent future occurrences.
Note: The episode concludes with promotional content for the Legal AF YouTube channel, which the hosts encourage listeners to subscribe to for more in-depth discussions on law and politics.