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The Chaos Inside Trump’s Legal Team

His attorneys describe a dysfunctional operation as they expect more indictments.

Photo-Illustration: Intelligencer; Photos: Getty
Photo-Illustration: Intelligencer; Photos: Getty

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One of the latest setbacks in Donald Trump’s many legal cases came from within his own team when attorney Tim Parlatore left the group and publicly blamed Trump adviser Boris Epshteyn for his departure. The problems within the group are deeper and more complex than Epshteyn, however, according to conversations I have had in recent days with some of the lawyers currently defending Trump in some of his most significant and perilous legal entanglements. They agreed to talk to me on the condition of anonymity and were careful not to violate attorney-client privilege by speaking about the specifics of any case, but it was clear from our conversations that there are serious problems with the effort to defend the former president.

“It’s not quite as dysfunctional as the media portrays it,” one of Trump’s lawyers told me about the group, but “to the extent it is dysfunctional, it does negatively affect things.” Another lawyer told me the media’s depiction of Trump’s legal team as disorganized and riven by interpersonal conflict is “fair but slightly overstated.”

On Monday, several Trump lawyers were spotted meeting with Justice Department officials, including special counsel Jack Smith, in an apparent bid to talk them out of bringing criminal charges against Trump in connection with his retention of classified documents at Mar-a-Lago and the subsequent efforts to stonewall federal investigators. Some of Trump’s lawyers told me they have already resigned themselves to what they see as the inevitable prospect of a federal indictment concerning at least the documents, even as they maintain that such charges would be legally unwarranted. News of the indictment became public on Thursday, when Trump announced he had been told to report to federal court in Miami.

These sorts of meetings are very familiar to federal prosecutors who have conducted complex white-collar criminal investigations (and, yes, as many have noted already, they tend to take place near the end of the investigation). In my past life, I was in the prosecutor’s seat for a couple of those discussions with the same lawyer leading the group on behalf of Trump on Monday, a former federal prosecutor turned defense lawyer named Jim Trusty. He fits a recognizable type in the white-collar bar — affable, plainspoken, and experienced in a broad array of criminal investigations — but he is also something of an oddity. He works at a relatively small and little-known Washington law firm whose principal focus, at least until recently, was online gambling and internet fraud.

Trump’s legal team is fractured across various jurisdictions and investigations, from New York to Washington to Florida to Georgia, and there is virtually no coordination among the attorneys. There is also no credible or unifying figure at the helm, which will increasingly complicate matters for Trump — particularly as decisions from prosecutors at the Justice Department and in Georgia are reportedly looming on the horizon, as Trump faces a major civil-enforcement action from the New York attorney general that will go to trial in October, and as the criminal case against Trump in Manhattan heads toward a trial currently scheduled for March.

The group itself is an odd bunch. As with Trusty, some were known quantities in their respective areas of practice well before their work for Trump — people like Ron Fischetti, who has reportedly been working most recently on the New York attorney general’s civil fraud case against Trump and his company; Chris Kise, a former solicitor general of Florida who worked on the effort to halt the Justice Department’s review of the documents seized from Mar-a-Lago; Joe Tacopina, the New York lawyer who was initially engaged to defend Trump in the civil case brought by E. Jean Carroll and is now defending him in the Manhattan DA’s prosecution over the hush-money payment to Stormy Daniels; and Todd Blanche, a former federal prosecutor in Manhattan who successfully represented Paul Manafort in New York and left a large law firm to defend Trump alongside Tacopina in Manhattan criminal court.

Other lawyers have had more eclectic qualifications and taken unusual paths to represent Trump. Parlatore, who once served in the Navy but has not previously worked at the Justice Department, rose to national prominence defending former Navy SEAL Eddie Gallagher, whom Trump later effectively pardoned. Still others appear to have virtually no relevant experience, such as Christina Bobb, a lawyer and former host for the right-wing One America News Network who found herself working for Trump last year before she reportedly got herself ensnared in the criminal investigation at Mar-a-Lago.  

One of the lawyers currently working on Trump’s sprawling legal-defense team drew a sharper, more provocative distinction. “You’re either one of two people as a lawyer for Donald Trump,” the attorney told me. “The ones who say ‘yes’ to everything, who will get sanctioned and get disbarred, who go to courts claiming election fraud that doesn’t exist, or who get put in a difficult position” owing to their service to Trump. “He gets these lawyers who just want to be part of that Trump world.” Others, in this person’s view, are more experienced, professionally secure, and independent minded and do their best to represent Trump within the boundaries of professional rules and norms.

Ordinarily, a person of significant financial means facing several serious government investigations would try to select a single national law firm to manage the effort, perhaps in partnership with reputable local counsel in the relevant jurisdictions. There are certainly variations on that scenario, including an array of midsize or prominent boutique firms that can field highly capable and experienced defense teams, but ideally, the team of lawyers is strategically, tactically, and even temperamentally aligned. A smaller number of firms also improves coordination and information sharing among the team and reduces competition and infighting among lawyers, particularly since financial incentives are more closely aligned when lawyers work at the same firm.

Whatever the precise structure, ideally the group members are in frequent communication with one another so they are aware of what may be happening in other jurisdictions; so they can review and coordinate legal filings to eliminate any potential inconsistencies across factual claims, legal positions, and even tonality; and so they can share government requests or subpoenas and ensure the responses are comprehensive and uniform, including with respect to the assertion of legal privileges that could inadvertently be waived. That is particularly the case when you have a prosecutor working on multiple major fronts, as Smith is, or when you have multiple prosecutors looking at the same fact pattern, as with the overlapping investigations concerning Trump’s effort to remain in power after the 2020 election that are being run separately by Smith and down in Georgia by Fulton County prosecutor Fani Willis.

Multiple lawyers working for Trump, however, told me there is no meaningful coordination across the groups. There are no standing meetings or calls — a common feature of large defense teams handling complex matters on behalf of a single client — to provide updates or compare notes among the groups. Even today, some of the lawyers working on Trump’s most important matters have never met or even spoken to one another, and they have little insight into what’s happening in the proceedings they aren’t directly working on. “You do what you do, then we all convene later and find out later what everyone else has done,” as one of them put it.

Adding to the chaos have been frequent staffing changes and the conspicuous shuffling of lawyers in and out of teams, which is inherently disruptive and at times has generated some understandable friction among the lawyers involved. Parlatore’s recent departure was just the latest example; his public comments about the internal workings of the team (the disclosure about Epshteyn objecting to additional searches for documents, in particular) have rankled some of the remaining lawyers. In addition, according to public reports, Kise has ended up in a less prominent position than initially anticipated; he was expected to maintain a leading role in the documents investigation. (He reportedly did not attend Monday’s meeting at the Justice Department.) There were also relatively last-minute staffing changes on the team defending E. Jean Carroll’s lawsuit (Tacopina was added to a team that was until then being led by Alina Habba) as well as the team defending Trump in the Manhattan DA’s investigation (with the relatively late addition of Tacopina and, later still, Blanche).

Some of the lawyers I spoke with acknowledged how strange it is that an ostensibly wealthy former U.S. president finds himself with such a professionally and geographically fractured group, but they cited a variety of explanations, all having to do with Trump himself. One reason, they said, is that Trump is cheap and has apparently been reluctant to spend the sort of money his legal circumstances would seem to demand. Another is that he seems to have a high tolerance for chaos and dysfunction and perhaps even enjoys being able to shuffle lawyers around based on his whims, however unwise it may ultimately be.

There is also a very serious question about the number of sizable, reputable law firms that would even take Trump on as a client at this point, particularly since most of them are based in Manhattan (where Trump is widely loathed); since so many lawyers have gotten into major trouble working for Trump; and since the media have cast a harsh light on large firms like Jones Day, whose legal work was integral to Trump’s first campaign and administration.

Fundamentally, this would seem to be a Trump problem, a function of his long, rich history of erratic and unfocused management, which has been documented in both his business and presidential roles. But after Parlatore left the team, he pointed a sharp finger in the direction of Epshteyn, who serves in a role that loosely approximates an in-house counsel or personal lawyer for Trump in addition to his campaign responsibilities. According to Parlatore, Epshteyn impeded efforts by Trump’s lawyers to conduct searches for more classified documents after the search of Mar-a-Lago and was “not very honest with us or the client” — a seemingly damning assessment of someone whose job supposedly includes managing the flow of information between Trump and his various lawyers.

As with all things Trump, however, you will get a slightly different perspective on the matter depending on whom you speak with in the former president’s orbit. One lawyer currently working for Trump insisted that Boris Epshteyn “doesn’t manage me” before proceeding to criticize his lack of “experience as a litigator.” This person explained, “He’s not really an attorney,” adding, “If you ask me what I think about Boris, I share the same sentiments [as Parlatore]. I think, frankly, all the lawyers do.”
Another lawyer told me, “Boris is exactly who you think he is. He’s a yes-man. He’s an enabler. He thinks suing people is the answer to everything.” In particular, this person cited the civil complaint filed on behalf of Trump against Hillary Clinton, which was tossed out, and a pending lawsuit against Michael Cohen, both of which drew some skepticism among Trump lawyers who weren’t directly involved in preparing the complaints.

I asked the same person whether Epshteyn’s performance was emblematic of broader disorganization across the defense teams and whether that was ultimately hurting Trump himself. The answer was quick and unequivocal: “Yes. Without a question.”

Yet another lawyer took sharp issue with Parlatore’s diagnosis of the situation and insisted Epshteyn was not standing in their way. “Every single one of Trump’s lawyers has his cell-phone number, and he will pick up on the first ring,” this person told me. “If he doesn’t pick up, it’s because he’s giving a speech. He’ll pick up even when he’s golfing. The idea that there’s this buffer is an insane lie.”

That lawyer went on to explain that the atomized, decentralized nature of Trump’s legal defense remains a significant problem apart from Epshteyn. “Substantively, it matters because you have one individual who is facing three separate criminal investigations, or really four if you say January 6 is its own, and who is actively running for president,” the attorney said. “It is a major machine. He has a staff of campaign folks putting out a message that necessarily has to include these investigations, so not having a central brain trust that knows intimately what’s happening in all four investigations and then can communicate that to Trump and among the lawyers and to the campaign staff, it creates dysfunction. It just does. There’s no way it doesn’t.”

Those observations point to a central paradox of Trump’s current legal situation, particularly as it relates to the pending criminal investigations and the prosecution in Manhattan. His reelection campaign appears to be a central component of his legal-defense strategy, since, if successful, a second term as president would allow him to shut down any pending federal prosecutions and investigations and would provide him with a potent justification for putting any state proceedings on ice. But as an electoral matter, Trump thrives on conflict and grievance. On the campaign trail, he has repeatedly posited an elaborate theory of political persecution at the hands of prosecutors, and by all outward appearances, Trump seems to be quite comfortable being publicly locked in an intensely adversarial dynamic with the Justice Department.

A productive legal defense in complex matters, however, tends to involve some level of humility, compromise, and conciliation — traits that are fundamentally incompatible with Trump’s public and political personae and ones he seems incapable of modeling even briefly. Early last year, for instance, Trump could have easily cut short the criminal investigation concerning the documents at Mar-a-Lago if he had simply returned everything and made some slight display of contrition. There might very well have been an opportunity even after the search of Mar-a-Lago to resolve the investigation along similar lines, but Trump resorted to attack mode and has publicly been stuck there ever since.

This could all conceivably work out in Trump’s favor in the long run if he manages to get reelected, but in the short term, the dynamics are problematic for him whether he realizes it or not. At the moment, he lacks the sort of disciplined, unified, credible, and coordinated legal-defense team he would need to maximally serve his interests, and the current situation will only get worse if more cases pile up, leading to more court appearances, more diversions from the campaign trail, and more high-stakes legal battles that could pose both personal and political risks.

Meanwhile, the knock on Smith and a number of the prosecutors working under his supervision — including former colleagues with whom I have spoken in the months since his appointment — is that, if anything, they may be temperamentally inclined to charge too many people and too many crimes. In private, some former federal prosecutors who have worked with Smith and his colleagues have expressed mild concern (they all mostly hate Trump, so no one is terribly worried) about the possibility that Smith could end up bringing a high-profile prosecution that fails (again) or gets reversed on appeal (again). Whatever one makes of that critique, the intensely adversarial posture Trump has adopted cannot possibly be helping him in strictly legal terms as he and his lawyers navigate the crucial months ahead across from Smith and his team.

At this point, the situation may very well be beyond repair, but there is only one person who could ever conceivably fix this. It is not Epshteyn but the client himself, a man who has practically dedicated his life to high-level chaos and dysfunction in all of his pursuits. When he was in office, this was a national problem with serious national implications, but this time around, Trump’s political opponents will be watching and rooting for him to stay the course.

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