Trump’s legal strategy is a great way to wind up in prison

If you want to get convicted, hire lawyers who tell you what you want to hear.

Michael Cohen, a personal attorney for Donald Trump (Photo By Tom Williams/CQ Roll Call)
Michael Cohen, a personal attorney for Donald Trump (Photo By Tom Williams/CQ Roll Call)

At least on paper, Donald Trump is a lawyer’s dream client. He’s not just world famous, he may someday become the most high-profile criminal defendant on the planet. He runs up massive legal bills, and actually has enough money to pay them (or so he claims, anyway). And who wouldn’t want to be able to advertise to potential clients that they once represented the President of the United States?

And yet, elite attorneys largely treat Trump as Typhoid Mary. Earlier this week, former Solicitor General Ted Olson rejected an offer to join Trump’s legal team — for the second time. Last June, Olson was among lawyers from four of Washington, DC’s top law firms who reportedly turned down Trump as a client, including another former Solicitor General, Paul Clement.

As one lawyer told Yahoo News at the time, “the concerns were, ‘The guy won’t pay and he won’t listen.‘”

Then, on Thursday, John Dowd — the lawyer who led the legal team representing Trump in Special Counsel Robert Mueller’s investigation into Russian interference with the 2016 election — resigned. According to the New York Times, he did so because “Mr. Trump was increasingly ignoring his advice.”


That leaves Trump with a ragtag band of personal attorneys to defend him in the Mueller probe. Some of these lawyers, to be sure, have very serious legal credentials. Others are a bit more goofy. But there appears to be one unifying theme among Trump’s legal team — a tremendous personal alignment with Trump’s own viewpoint.

Trump is surrounded by yes men, and he’s likely to regret that fact. A lawyer’s job is to provide objective, realistic advice to their client, not to tell the client what they want to hear. And a client who won’t hire lawyers that tell him the truth is likely to find themselves in deep trouble.

As Dowd departs, Trump’s newest hire is Joseph diGenova, a former federal prosecutor best known for spouting conspiracy theories on Fox News. In one of his many Fox appearances, diGenova told Fox’s Tucker Carlson that there “was a brazen plot” within the FBI to “illegally exonerate Hillary Clinton, and, if she didn’t win the election, to then frame Donald Trump with a falsely created crime.”

DiGenova, it should be noted, is a former United States Attorney with very serious legal credentials, so it is unclear whether he actually believes the conspiracy theories he’s repeated, over and over again, on Fox News, or if he’s being careerist in a calculated, cynical way. It is possible, as the Washington Post’s Aaron Blake notes, that diGenova’s conspiracy mongering appearances were “auditions for joining Trump’s legal team.”


But regardless of whether diGenova is a true believer or a charlatan who went on TV to advertise for a single, particularly high-profile client, it’s hard to imagine him being an effective member of Trump’s legal team now that he’s got the job.

Suppose that, after looking at the evidence against his new client, diGenova concludes that Trump is in serious legal jeopardy —  including in New York state court, where Trump can neither fire prosecutors nor issue pardons — and that Trump’s best course of action is to seek a plea bargain that avoids jail time. How would diGenova possibly have credibility to break this bad news to his client after he just spent months claiming that the allegations against Trump were a grand conspiracy by the Deep State?

DiGenova joins two of Trump’s longtime personal attorneys as members of the president’s legal team (Kasowitz reportedly “stepped back last summer,” but is in contact with Trump and “could take on a larger role again.”) Like diGenova, Marc Kasowitz has impressive legal credentials, but few of those credentials suggest that Kasowitz is the right lawyer to advise a major politician on a high-profile criminal probe involving allegations that strike at the heart of the national interest.

Kasowitz built his career by suing big banks and litigating major cases involving securities law. This is serious legal work, and Kasowitz may be the ideal attorney to hire if you want to sue Goldman Sachs. But that sort of work does not give him the kind of intimate knowledge of the Justice Department’s inner workings that a Ted Olson or a Paul Clement would have brought to the table.

What Kasowitz does bring to the table is a distinctly Trumpian desire to throw elbows at his opponents. According to the New York Times, Kasowitz urged Trump to take a more “combative approach” to the Mueller investigation — and Trump, who recently attacked Mueller for the first time on Twitter, appears to have embraced this approach.

That may satisfy Trump’s combative instincts, but it is rarely a good legal strategy. Innocent people typically don’t attack the prosecutor. They are much more likely to cooperate because they want to show that they have nothing to hide.


Another of Trump’s longtime lawyers is Michael Cohen, who claims that he paid porn star Stormy Daniels $130,000 of his own money to cover up Daniels’ relationship with Trump. Cohen, in other words, is either so devoted to Trump that he’s willing to write enormous checks on his client’s behalf, or he is so devoted to Trump that he’s willing to lie about writing enormous checks on his client’s behalf. Neither of those options suggest he will provide dispassionate legal advice.

And then there’s Jay Sekulow.

Sekulow may be the oddest character in Trump’s band of misfit attorneys. An accomplished appellate attorney, Sekulow built a name for himself by litigating cases on behalf of religious right clients. Sekulow also founded at least two legal non-profits, which are ostensibly charities, but that also appear to have made Sekulow fantastically rich.

According to a multi-year investigation into these organizations, “the two charities paid out $15.4 million to Jay’s law half-owned law firm, $5.7 million to Gary,” Jay Sekulow’s brother, “$1.6 million to Jay’s wife Pam, and ‘$2.74 million in private jet lease payments to companies owned by Jay Sekulow and his sister-in-law, Kim Sekulow’” Additionally, “Sekulow-linked companies also ‘earned $2.89 million for space rental, media production and administrative work.’”

Meanwhile, Sekulow’s public performance as Trump’s attorney speaks for itself. In a June 2017 interview with Fox News Sunday, Sekulow alternatively claimed that Trump is under a Justice Department investigation, that Trump isn’t under a Justice Department investigation, and that Sekulow doesn’t know whether Trump is under a Justice Department investigation.

Trump, of course, is also being advised by lawyers within the White House Counsel’s office, including attorney Ty Cobb. But as a government lawyer, Cobb’s role is limited. Among other things, the federal appellate court that oversees the District of Columbia has held that government attorneys cannot invoke attorney-client privilege to avoid a grand jury’s demand for information. So Trump would be foolish to rely too heavily on Cobb for confidential advice.

And, in any event, Cobb appears to be falling out of Trump’s favor. As the legal news site Above the Law puts it in a pointed headline, “Trump Contemplates Axing Ty Cobb, His Only Competent Attorney.”

It’s probably going too far to label diGenova, Kasowitz, or even Sekulow as incompetent attorneys. All have impressive achievements within their areas of expertise. But none of them appear suited to offering painful, objective advice to their most high-profile client. That’s a potentially disastrous shortcoming in a defense attorney.