Trump’s Biggest Legal Headache Is Finding Lawyers Who Want To Represent Him

Normally attorneys would be jumping at the chance to represent the President of the United States. With Donald Trump, the lawyers are distancing themselves from him as fast as they can.

Donald Trump is having significant trouble finding lawyers to represent him in the ongoing Russia investigation, with several top Republican lawyers refusing in recent days to join a legal team that has proven to be chaotic and disorganized, in no small part because they’re representing a client with a long history of not listening to advisers, legal or otherwise. The process began last week when John Dowd, who had been heading up negotiations with Special Counsel Robert Mueller about Trump eventually answering questions from Mueller and his investigators, resigned as Trump’s counsel abruptly as it became apparent that Trump wanted to pursue a more aggressive posture toward the Russia investigation itself. That announcement came just days after it was reported that Joe DiGenova and his wife Victoria Toensing would be joining the Trump’s legal team, and it was no doubt spurred in part by the addition of DiGenova and Toensing to the legal team. DiGenova in particular was a notable selection because he has made a name for himself most recently as a legal commentator on Fox News Channel and, in his many appearances, has pushed the rather implausible conspiracy theory that the Department of Justice was at the center of a “Deep State” conspiracy to undermine the Trump Presidency. That decision was seen by many as a sign that Trump wanted his defense to the Mueller investigation to take a far more aggressive turn and which could ultimately include trying to fire Mueller himself. In the end, it was announced that DiGenova and Toensing would not be joining the Trump defense and while it was claimed that the reason for this announcement was a conflict of interest due to other clients they represented, it has also been reported that the decision came in the wake of a meeting between the couple and Trump after which Trump told friends that he didn’t like their appearance and didn’t have chemistry with them.

That was just the beginning of Trump’s troubles, though.

A few days after Dowd had resigned it was reported that Trump’s advisers had reached out to Ted Olson as a possible addition to Trump’s defense team. Olson, of course, is probably one of the most famous Republican lawyers in Washington given his service in the Justice Department under President Reagan, his service as George W. Bush’s lead attorney in the legal disputes arising out of the 2000 election in Florida that ultimately resulted in the Supreme Court’s Bush v. Gore  decision, and his service as Solicitor General of the United States during President George W. Bush’s first term. Later, Olson earned nationwide fame as one of the top attorneys in the country leading the fight against laws barring gay and lesbian couples, most prominently including his work with David Boies, who had represented Al Gore in Bush v. Gore, in the lawsuit that ultimately led to the Supreme Court decision that struck down California’s Proposition 8 barring same-sex marriage. Within hours after the reports that the Trump team had reached out to him, though, Olson’s law firm announced that Olson would not be joining the team. As with DiGenova and Toensing, conflicts of interest with existing clients were cited as the reasons for the decision, but it was apparent that there was more to it than that. Olson himself seemed to confirm that when he called the staff turmoil around Trump “beyond normal” and stated this in a conversation with David Corn of Mother Jones:

I asked Olson about being recruited for Trump’s squad. He rolled his eyes, suggesting that this was never going to happen and that it was not just a matter of conflicts. (Though a conservative stalwart, Olson has in recent years enhanced his reputation by becoming a forceful advocate for gay marriage. Associating with Trump could well tarnish that shine.)

So this didn’t get too far? I queried. Olson shrugged in an I’m-not-getting-into-details way. “Who knows how these trial balloons happen?” he said, in a manner that definitely suggested he knows how they happen. He then joked, “Joe [diGenova] lasted longer. At least two days.”

So is Trump going to have trouble finding attorneys? Olson shrugged again. “Let me ask this a different way,” I said. “In the last few days has any lawyer come up to you and said, ‘I’m willing to work for Trump?'”

Without hesitation, Olson said, “No.” Not at all? “Not at all.”

Late yesterday, it was reported that yet another top Republican attorney had waved off a chance to join Trump’s legal team:

A prominent Chicago defense attorney said Monday that he had declined an invitation to lead President Trump’s legal team responding to special counsel Robert S. Mueller III’s Russia investigation, underscoring the president’s difficulty in attracting top legal talent to represent him in the probe.

Dan K. Webb, a Republican, is a former U.S. attorney for Illinois and a corporate and white-collar-defense lawyer for the firm Winston and Strawn.

In a statement, his firm said the president and his team recently reached out to Webb and D.C.-based partner Tom Buchanan.

“They were unable to take on the representation due to business conflicts. However they consider the opportunity to represent the President to be the highest honor and they sincerely regret that they cannot do so,” the firm said. “They wish the president the best and believe he has excellent representation in Ty Cobb and Jay Sekulow,” referring to the two lawyers now handling Trump’s defense.

For his part, Trump proclaimed in a series of Tweets over the weekend that he wasn’t having any trouble finding lawyers at all:

Notwithstanding Trump’s protestations, the opposite appears to be true. Rather than gaining the services of top Republican lawyers from around the country, Trump has been losing attorneys at a quick pace. One of the first to jump ship was Mark Kasowitz, who had represented Trump in many civil matters in the past, but left the team back in July.  Other departures of lesser-known attorneys followed in subsequent months, leaving us now at the point where the top lawyer in Trump’s personal legal team appears to be Jay Sekulow, who has largely made his name as an appellate lawyer representing clients on the religious right and appears to spend most of his time as Trump’s lawyer on cable news defending Trump. In any case, Sekulow doesn’t really have much experience in criminal defense generally or in the high stakes area of criminal defense in Federal proceedings such as the Mueller investigation. The other prominent face in Trump’s Mueller defense team, Ty Cobb, is actually employed via the White House Counsel’s office and doesn’t directly represent the President personally. Given the top-notch team of prosecutors that Robert Mueller has assembled, it appears quite apparent that the President is at a big disadvantage right now.

Notwithstanding the fact that the attorneys who have recently declined to represent Trump have cited conflicts of interest as the reason that they couldn’t represent the President, it also seems apparent that there are other factors at play. In the weeks after the 2016 election, for example, there were several reports that top Washington, D.C. and New York law firms had turned down opportunities to represent Trump with regard to his efforts to disentangle himself from his businesses prior to taking office. In many of those cases, the decision appeared to have come after other clients objected to the idea that the firms in question could end up representing Trump and threatened to pull their business from the firm. Much of this was due to the controversial statements that Trump had made throughout the campaign regarding minority groups and others, and when faced with the decision between representing Trump on one case and losing business that probably brings in millions of dollars per year in billings, the choice was obvious. Similar concerns may be motivating law firm decisions today. In addition to that, we have seen over the past fourteen months that Trump is a man who often doesn’t listen to his advisers, acts out on his own based on what he sees on Fox News Channel, and simply being an erratic and uncontrollable client. Finally, as I noted on Twitter this morning, Trump has a long history of not paying people who he owes money to, and of significantly underpaying what is owed when he does pay. Why would any lawyer want a man like that for a client even if he is the President of the United States.

FILED UNDER: Law and the Courts, US Politics, , , , , , , , , , , , , , , , , , ,
Doug Mataconis
About Doug Mataconis
Doug Mataconis held a B.A. in Political Science from Rutgers University and J.D. from George Mason University School of Law. He joined the staff of OTB in May 2010 and contributed a staggering 16,483 posts before his retirement in January 2020. He passed far too young in July 2021.


  1. Grumpy Realist says:

    A lifetime of not paying one’s bills is finally landing…

  2. Kathy says:

    It’s hard to believe armies of lawyers are not lining up for a chance to be stiffed by Donnie Dennison.

    Does the Constitution or the law provide an impeached official with a public defender?

  3. @Kathy:

    If he were a criminal defendant he would be entitled to the same rights as anyone else, but given his personal wealth he would not qualify for court-appointed counsel in any court in the country.

  4. Kathy says:

    @Doug Mataconis:

    I’ve always thought he should represent himself anyway. No one is a more fitting client for Trump. Though he might not want to do it because he knows he won’t get paid.

  5. CSK says:

    The reason Trump stiffs so many hundreds of people isn’t just that he’s cheap. He enjoys it. Nothing, absolutely nothing, gives him greater pleasure than screwing a dishwasher at one of his golf clubs out of overtime pay.

  6. Daryl's other brother Darryl says:

    I think there is more to this than the above.
    For one…working for Dennison, a known racist and misongynist, would destroy the brand of most firms.
    Second…I have to think most women and non-whites would immediately quit your firm. And then there are the recruitment issues…who is going to want to come to work for you?
    No large firm can afford to be as one-dimensional as working for someone like Dennison would force you to be.
    The Dennison brand is toxic. Why have that rub off on you?

  7. CSK says:


    Then he could challenge the inevitable guilty verdict on the grounds that he had grossly incompetent and inadequate representation.

  8. Lit3Bolt says:


    “Your Honor, the Court’s sentence is unconstitutional, as being me is itself a cruel and unusual punishment.”

  9. rachel says:

    @Grumpy Realist:
    Lets say that you’re an expensive, elite lawyer. You can pick and choose your clients, but you’re going to step up for:
    a client who will lie to you?
    a client who can’t understand, let alone follow your good advice?
    a client who will always be making more work for you with the metaphorical grenades he lobs out at least once a week?
    a client who will expect you to throw yourself on those grenades, destroying your reputation to protect him from the problem he just made?

    And to top off la coupe de glace à la merde, a client who is notorious for not paying his bills?

    Yeah, no. Not unless he puts up the whole estimated payment up front in an escrow account he can’t touch, and probably not even then because who needs this grief?

  10. grumpy realist says:

    @rachel: I have mentioned many times the comment made by one of Rod Blagojevich’s lawyers, when quitting: ” I don’t insist that my clients take my advice, but I do think they should at least listen to it!”

    It’s already obvious that being Trump’s lawyer is going to be an all-around pain-in-the-neck and a good way to lose one’s reputation. The only people who would be interested are a) the very greedy, or b) those without a reputation to lose.

  11. Kathy says:


    You left out: a client who is convinced he knows more about the law than you do, therefore your advice is stupid, you’re stupid, and you don’t deserve to get paid. Oh, and you’re lucky he doesn’t sue you.

  12. Stormy Dragon says:

    Problem is that a new lawyer or law firm will take months to get up to speed (if for no other reason than they can bill more)

    The new lawyer hasn’t even been hired and Trump is already trying to throw him under the bus.

  13. rachel says:

    Here’s a thought: what if Donnie Derps is deliberately driving his lawyers away so that when Mueller Time comes, he can decline to give any statements because he has no lawyers to counsel him?

  14. inhumans99 says:

    @Grumpy Realist:

    Yeah, you are right and I honestly do believe that racking up tens of thousands in billable hours and not getting paid is the true reason why some heavy duty lawyers are genuinely hesitant to step into the fray. It would be devastating for a firm to hand President Trump a bill for say $150,000 and have the President say good luck with that, I asked you to find a way to make it so I can legitimately declare myself President For Life and you failed so you are fired (while the lawyers stammer Mr. President Sir we already put in the labor so you need to pay us).

    My bad attempt at humor aside I genuinely do believe that President Trump’s reputation for stiffing people who work for him is indeed the problem (regardless of whether you are a Mar-A-Lago dishwasher or work for the firm that helped build Trump Tower).

    On the other hand if Michael Cohen offered to pay the bills perhaps attracting counsel would not be an issue, after all he is President Trump’s bestie, right?

  15. grumpy realist says:

    @inhumans99: Well–it’s six of one or half-dozen of the other. Let’s say that Trump’s reputation of not paying his bills certainly isn’t making a top-notch lawyer more inclined to jump on board. And then there’s all the other stuff (Lil Donnie not listening to his lawyer, not following his instructions, acting like a whiny toddler, flying off the handle…etc. etc. and so forth) which makes Trump even more of a Pain In The Ass.

    In short, Trump would be The Client From Hell and everyone so far has looked at the situation and said, nope nope nopity nope. They don’t NEED Trump as a client, don’t WANT Trump as a client, and would prefer to stay as far as possible from that barrel of excrement.

  16. Kathy says:

    Free advice to prospective lawyers wishing to take this dumpster fire of a client:

    “Mr Dennison, we require a retainer of $10,000,000.00 US Dollars in the form of a cashier’s check made out to Connem, Chethem & Howe before we do any work at all.”

    The actual figure for the retainer and the name of the law firm may vary.

  17. michael reynolds says:

    No, no, everything is fine, just fine. The WH is working like a Swiss watch. All the best people, because Trump is really smart, dontcha know.

    Isn’t that right, @Bung and @JKB and @Paul L and @Guarneri?

    The President of the United States is so toxic that lawyers won’t touch him. Lawyers! Manson had lawyers. Jeffrey Dahmer had lawyers. But lawyers want nothing to do with the ‘leader of the free world.’ Fortunately that’s not a problem, because no one in the history of the world has been as brilliant and wonderful as Trump, and he’s playing — dimensional chess and will outsmart everyone!

  18. Moosebreath says:


    The old saw that the person who represents himself has a fool for a client seems appropriate.

  19. Kathy says:

    @michael reynolds:

    No, no, everything is fine, just fine. The WH is working like a Swiss watch.

    Oh, but it is!

    Like a Swiss watch run over by a steamroller. 🙂

  20. MarkedMan says:

    Trump is right though. I’m sure there are many, many lawyers that would fall over themselves to represent him. That’s not the problem. The problem is that there doesn’t seem to be any top tier lawyers in that category. But for lawyer who is largely unknown, halfway through their career and stuck in a rut, being Trump’s lawyer for even a few weeks might be worth not getting paid. There are gullible people who would see that on your resume and think you must be a genius. And we know that such poor fools exist because of Trump University, Trump Wine, Trumps Sh*tty Condos, and so forth.

  21. gVOR08 says:

    When it comes to lawyerly ethics, Atrios is the only one who has it right:

    Everybody Has Their Price
    There are respected lawyers in DC who would happily represent genocidal dictators, and I don’t just mean in a “well, even the worst criminal defendants deserve legal representation” sense. I mean advocate for their right to continue to commit genocide.

    If Trump can’t get a good lawyer it’s because he won’t pay them a big sum of money up front.

    Can you write articles of impeachment that include, “If the President is too cheap to afford a lawyer the Senate will appoint one for him.”?

  22. grumpy realist says:

    An interesting theory relayed on by Josh….

    If this is true, then…..YYYEEESSS! (punches air)

  23. michael reynolds says:

    It’s not just that Trump won’t pay them, if they represent Trump their regular corporate clients will bail. He’s that toxic. Cravath or Baker McKenzie can rep Trump and lose clients with billings stretching back ten years and ten years into the future. Would you trade Trump for Starbucks?

    And the big firms all recruit from the same schools. Do you think the head of the law review at Harvard law, with a choice of basically any firm, is going to choose the Trump firm? Why?

  24. CSK says:


    Trump only wants lawyers who’ll tell him what he wants to hear.

  25. MarkedMan says:

    I don’t think it’s just that repping Trump, in and of itself, is a black eye for a firm, although I’m sure that’s a consideration. But smart people have observed that Trump makes everyone look bad. Rex Tillerson was CEO of one of the largest companies in the world. Who do you think will hire him now? Reince Priebus was considered a solid A lister in Republican Party circles. Now those same people see him as a clown. Just look at all the people who have already left the Trump adminstration. Can you name a single one that went on to something that was as least as prestigious as what they had before throwing their lot in with Trump.

    Bottom line: a law firm has to protect its reputation as competent. It can defend reprehensible clients and survive. But it cannot afford being made to look like a bunch of confused losers getting in and out of the clown car.

  26. HarvardLaw92 says:


    This is closest to the truth. We were one of the firms he approached, and indeed for a period of time his company was a client (I take credit for personally forcing the firm to end that relationship).

    The bottom line is that we just can’t afford to be associated with him. We don’t need the negative PR and we don’t want the visuals. It really doesn’t matter what he would be willing to pay or whether he sent a cashiers check upfront. We won’t go near him because no matter what happens, we’ll be sprayed with the stink of being associated with him.

    At this point, he’s radioactive. No other top tier firm is going to touch him, for the same reasons. He’s stuck with Jay Sekulow …

    Nutjob Jay Sekulow against Bob Mueller and the prosecution team that gutted the Gambinos. Let that one sink in for a few moments … 🙂

  27. michael reynolds says:

    I was just on the phone with my lawyer on another matter* and asked him if he knew anyone in the NY legal world who might take Trump up on his offer.

    I’m hoping I don’t get billed for the time he spent laughing.

    *Just got my first paying Hollywood gig. Yay?

  28. CSK says:

    @michael reynolds:

    Congrats. Did you sell one of your books, or is it a screenwriting gig?
    Some unsolicited advice:
    1. Keep your sense of humor
    2. Remain detached
    3. Always, always act as if they need you more than you need them.

  29. michael reynolds says:

    Well, I can’t be specific, but a property in which I have an interest is being adapted and going to script and I’ve wheedled my way into the room. I even get paid. Plus I get an excuse to drive down to LA, and I like LA.

  30. michael reynolds says:

    #3 is how I wheedled my way into the room.

    Are you employed in what I refer to as the Industry (but only ironically)? Had my first encounter with studio lawyers (other than options) and expect to be able to sit down in a few days.

  31. OzarkHillbilly says:

    @michael reynolds: Congrats. I think. 😉

  32. CSK says:

    @michael reynolds:

    No, I’m a writer. Or, as they say in L.A., an author, since writer there always means screenwriter. I received option money, purchase price, and a weekly consulting fee plus expenses for a book of mine I sold years ago. The movie was never made, but since I got all the money, I didn’t care. Hollywood assumes, probably with reason, that most people are dazzled when they come calling, so when they meet someone who isn’t dazzled, they turn accommodating and then obsequious.

  33. michael reynolds says:

    If you feel like it, shoot me an email. If I ever get down there (at this rate, who knows) I’ll buy you a drink and pick your brain. michaelreynoldsgrant (at) g (dot) mail.

  34. HarvardLaw92 says:

    @michael reynolds:

    Well done 🙂 Good on ya.

    Hope it doesn’t involve too much involvement with my shark brethren at the studios. They’re killers

  35. Barry says:

    @rachel: “…the metaphorical grenades he lobs out at least once a week?”

    You misspelled ‘several times a day’ 🙂

  36. Barry says:

    CSK says:

    “No, I’m a writer. Or, as they say in L.A., an author, since writer there always means screenwriter. I received option money, purchase price, and a weekly consulting fee plus expenses for a book of mine I sold years ago. The movie was never made, but since I got all the money, I didn’t care. ”

    From what other authors have said, you’ll get the money, but be prepared for your ‘child’ to be horribly mutilated and abused.