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Dear Reader,

As the summer draws to a close, we still don’t know whether Donald Trump will someday be indicted. It now seems more likely than when we held our Memorial Day barbeques, given the expansion of DOJ’s January 6 investigation (which now, finally, appears to be focused on the real centers of power and not merely on the riffraff who physically stormed the Capitol), the sudden jolt of activity from the Fulton County DA (after she waited a year-and-a-half to seat a grand jury), and the unexpected search of Mar-a-Lago for highly classified documents.

In the face of these mounting pressures, Trump has lawyered up, which is a smart move, and his right. While he has survived thus far – largely in spite of rather than because of his assorted bag of attorneys – the genuinely dreadful lawyering around Trump will soon begin to take a more serious toll.

It’s never quite clear who exactly represents Trump on what at any given moment. He has a track record of failing to pay his lawyers, and otherwise falling out with them. One former Trump attorney, Ty Cobb, has been making the media rounds declaring that his former client should be investigated and likely will be indicted. (It’s a questionable ethical move, by the way, for any lawyer to publicly slag a former client.) 

The lawyers, for their part, have suffered fates ranging from federal conviction and imprisonment (Michael Cohen); to search warrants and pending investigations (Rudy Giuliani, John Eastman); to multi-million dollar defamation suits (Giuliani, Sidney Powell); to challenges to law licenses (Rudy again, plus Powell and Eastman); to subpoenas and compelled public testimony (Pat Cipollone, Don McGahn, Patrick Philbin; I’m including former Trump White House counsel, who do not technically represent the president personally, because Trump chose them and they worked to protect his interests, generally.)

It does seem like Trump has finally moved beyond the ghastliest dregs, at least in terms of his formal, in-court representation: Giuliani, Powell, Alan Dershowitz, Lin Wood, and Jenna Ellis haven’t appeared on any formal filings in many months. They continue to spew maniacal conspiracy theories to defend Trump in public, but their names now seem gone from the official court dockets.

The team that remains – again, as far as we can tell, given the rotating cast of characters – is more of a mixed bag. Trump has retained the services of Alina Habba; the Washington Post reports that “[h]er professional experience includes serving as general counsel to a parking garage company.” He’s also got Christina Bobb, a former host at the far-right One America News Network whose “prior legal experience at the federal level consists mainly of a handful of trademark infringement cases on behalf of CrossFit.” And Trump is represented by Lindsey Halligan, whose practice, the Post reports, “focuses on insurance claims at residential and commercial properties… A search of federal court records found no filings under her name.” 

On the higher end of the scale, Trump has retained Jim Trusty and Evan Corcoran. The good news is they’re both former federal prosecutors. (Trusty used to lead DOJ’s organized crime group and, as the SDNY co-chief of that same unit, I was supposed to run certain things by him – but rarely did, keeping with SDNY’s general disdain for supervision.) But the bad news is their work so far hasn’t remotely reflected their impressive pedigrees.

Take, as Exhibit A, Trump’s motion seeking appointment of a special master to review the Mar-A-Lago search documents for potential privilege issues, and other fairly mundane and uncontroversial relief. Trump’s legal team nearly blew it. Despite their modest ask of the court, they contaminated their motion with wild conspiracy theories and accusatory blather aimed at DOJ and various political figures. Worse, the filing was a procedural apocalypse – prompting the judge to reject it on various technical grounds amounting basically to “Who are you, why are you here, what do you want, have you told the other guys, and what on earth are you doing?” 

The judge charitably gave Trump’s team of bumbling advocates a chance to fix their mess and re-submit it. Trump’s team accordingly filed a new motion that was an improvement, but only in the sense that a D-plus is an improvement on an F. The judge (as I anticipated would happen, on air at CNN) has indicated a “preliminary intent” to grant the motion. But Trump’s lawyers were bad enough that they nearly gakked the legal equivalent of a three-foot putt.

It seems so obvious that it feels silly to say it out loud: the quality of defense lawyering matters. But I mean: it really matters – even more than the quality of prosecution, in my view. Prosecutors tend to fall within a fairly narrow band of competency and style. We all get trained up a certain way within DOJ, and we learn the same tactics and core values. Of course, there’s variation – I worked with many dazzling trial attorneys and a few who were just so-so – but overall, prosecutors are a solid and steady group. And criminal cases generally rise or fall not on the talents of individual prosecutors, but rather on the strength of the evidence. Prosecutors know and embrace this. You’re not the star of the show, one SDNY veteran told me when I was a rookie, the evidence is

But defense lawyering involves more variance. A brilliant defense lawyer can single-handedly win over a jury, largely through force of personality. I’ve written before about my experience prosecuting John Gotti, Jr., which ended in a hung jury and a mistrial. The defense lawyer in that case never filed a single brief or other legal document – to this day, I don’t know what his letterhead looks like, or if he has any – but he won over the jury with self-deprecating humor and a local, conversational folksiness. And I’ve seen less charismatic defense lawyers win cases through meticulous research, writing, and analytical ability. 

The flip side is even more stark. More than once (more than five times), I’ve watched some schlocko (to use the technical term) give a defense closing, after which I’d whisper to my trial partner, that actually helped us. I’ve seen defense lawyers botch cross-examinations of key witnesses, elicit damaging testimony from their own clients, and make self-defeating legal arguments to judge and jury alike. Put it this way: in my experience, defense lawyers typically have more influence over the outcome of a case than prosecutors do. 

The stakes for Trump will only rise in the coming months. Whether he gets indicted or not, decision day has to be approaching for the various prosecutors who are circling him. Thus far, Trump has slipped out of harm’s way through a combination of prosecutorial reticence (see Mueller, Robert), in-house solicitude (see Barr, William), blind political allegiance from his supporters or others too afraid to cross him (see impeachments, both), and just plain old dumb luck. But Congressional inquiries and civil suits and impeachment trials are one thing; a criminal charge is another. 

If Trump does find himself on the wrong side of an indictment, the case will not be ironclad. Any charge will, by necessity, require prosecutors to prove criminal knowledge and intent, to a unanimous jury, beyond a reasonable doubt. Trump is notoriously tough to pin down when it comes to his state of mind. He doesn’t email or text, so there won’t be one game-over document. He’s managed to keep his inner circle from flipping on him. And he speaks in a stream-of-consciousness manner, and with such baffling imprecision, that it’s tricky to isolate any one snippet and pin intent on it. 

In any case with so much at stake and so many evidentiary unknowns, defense lawyering can make all the difference. Trump needs to get serious and quit staking his future with the dregs and mediocrities of the profession. This isn’t a casting call for a movie or a reality show; this is court, and competency is everything. If Trump doesn’t straighten out his legal team, and soon, then he’ll suffer the consequences.

Stay Informed,