President Trump and his personal attorney, Michael Cohen, both seem to get themselves into avoidable legal trouble. (Yana Paskova/Getty Images)

Time and time again, President Trump and his associates have talked themselves into legal trouble. Trump’s splenetic tweets about foreigners were quoted in court opinions blocking his immigration initiatives. When Trump proclaimed he had no idea that his attorney Michael Cohen had paid adult-film actress Stormy Daniels for her silence, her lawyers cheered — the president had just handed them a very plausible argument that the nondisclosure agreement she signed with Cohen was unenforceable. Like his client, Cohen has caused problems for himself, careening from one ill-advised public outburst to another about Daniels, derailing his efforts to enforce the nondisclosure agreement and probably assisting the federal criminal investigation that culminated in searches of his home, office and hotel room this month. During special counsel Robert Mueller’s investigation, former Trump advisers Michael Flynn and George Papadopoulos have pleaded guilty to lying to the FBI, and indictments against his former campaign manager Paul Manafort and Manafort’s associate Richard Gates include similar charges. These are all self-inflicted wounds; any good attorney would advise against them.  

When wealthy and powerful people make such bad decisions, it’s tempting to assume they must have gotten terrible legal advice. But that’s rarely true. Yes, for most people, there is a crisis of good lawyering in America: Quality legal advice is too expensive. Our public defenders are overworked and underfunded. Few Americans can afford to litigate a civil dispute at all, let alone do so aggressively with elite lawyers. But when the rich and powerful — the self-styled “masters of the universe” — make legally disastrous decisions, it’s usually because they’ve either ignored their attorneys or self-indulgently chosen the wrong lawyers for the job.

The very qualities that lead people to wealth, power and fame can make them very poor consumers of legal advice; hubris is fatal to an effective attorney-client relationship. Trump prizes “loyalty” very highly, as many powerful people do. But real loyalty from an attorney doesn’t involve fawning over a client, refraining from criticism, or congratulating them for views both right and wrong. A good lawyer’s loyalty lies in being ready to give plain-spoken advice that will get you fired if your client’s in the wrong mood. An effective advocate’s loyalty isn’t about saying “Good idea” or “You’re right,” it’s about warning “Shut up” and “No, you shouldn’t do that” and “Yes, I understand you want to do that, but here’s why it’s a terrible idea.” Real loyalty looks like Cordelia, refusing to flatter King Lear at great cost, not like her sisters, praising him effusively to get more land.

So when I see Trump and Cohen running their mouths about the hush-money contract with Daniels, thereby putting themselves in greater civil and criminal jeopardy, I don’t assume they’ve gotten bad legal advice. I assume they’ve gotten at least some good counsel but have ignored it, because running their mouths is essential to their public personas. Trump believes he is the master of the deal — the man able to talk his way into whatever he wants. Cohen imagines himself an unmatched fixer, an artful wielder of power and influence to get results for clients. Those self-images are not consistent with shutting up for your own good just because some lawyer tells you to.  

In fact, the federal criminal justice system depends on hubris for prosecutors to prevail when they take on the powerful. Flynn, Papadopoulos, Gates — and perhaps Cohen — are merely the most recent examples. Media mogul Martha Stewart was convicted in 2004 of lying to the FBI in the course of an insider-trading investigation. Former George W. Bush White House aide Lewis “Scooter” Libby, recently pardoned by Trump, was convicted of lying to the FBI during a leak investigation . Gen. James Cartwright, pardoned by President Barack Obama, was convicted of lying to the FBI about his discussions with the press. Onetime Housing and Urban Development secretary Henry Cisneros pleaded guilty in 1999 to lying to the FBI about payments to his mistress. All of these people talked themselves into a federal conviction, almost certainly against the advice of their attorneys. Their undisciplined reactions to investigations — not the underlying crimes being investigated — were their downfall.

Prosecutors and federal agents are extremely adept at exploiting human foibles. Mueller knows from long experience that powerful people think they can talk their way out of trouble and resent lawyers telling them they can’t. He also knows that powerful people tend to favor action. Often, my first advice to a client is simply “Stop doing things” — stop trying to use your influence and connections and persuasiveness and industry experience to solve the problem of being the subject of a criminal investigation. Patience and watchfulness are usually the best strategy. But people who clawed their way to the top by dynamism are no good at sitting still.

Trump doesn’t seem to be getting particularly good legal advice about Mueller’s investigation right now. His most qualified outside attorney, John Dowd, resigned last month; his attorney Jay Sekulow is an able First Amendment litigator but not a criminal defense lawyer ; and federal prosecutors just filed court papers asserting that Cohen, his longtime fixer, is not “currently engaged in any significant practice of law.” This is also because of hubris, which, when it isn’t leading the rich and powerful to ignore advice, draws them to choose lawyers based on the wrong qualifications. Masters of the universe too often hire lawyers who flatter them, defer to them and uncritically support their chosen approach to a crisis. They fire or force out lawyers who tell them the cold truth. A penchant for flattery is useful at times, but it is not an effective tool in a federal criminal investigation. The same powerful people also select lawyers who seem prestigious or ideologically consistent, but who lack appropriate expertise. As a federal prosecutor, and now as a defense lawyer, I’ve seen wealthy defendants choose lawyers who are prominent in the media but have no idea how to defend a federal prosecution. I once watched a slick attorney familiar from cable news fumble through a federal sentencing, long on rhetoric but short on any grasp of the law. Never send a fixer or a talking head to do a criminal defense attorney’s job. Trump has relied on several lawyers who are very adept in their fields but have no experience in defending sophisticated criminal matters.

Even when the masters of the universe knuckle under and hire good lawyers, they’re notorious for undermining them. Take Cohen, who may or may not be a master of the universe but certainly behaves as if he thinks he is. At a recent hearing, his lawyers stood before U.S. District Judge Kimba Wood, asking her to delay federal investigators from reviewing Cohen’s seized records. They didn’t bring Cohen to court. That was shrewd: If he wasn’t there, he couldn’t be forced into the difficult choice between incriminating himself by responding to one of Wood’s questions or else publicly refusing to answer. A sensible client would have waited patiently at home. But Cohen lounged ostentatiously on a nearby boulevard, smoking cigars in an aggressive sport coat and mugging for the press. This served to emphasize that he was deliberately absent so that he couldn’t be confronted with questions only he could answer — for instance, about his client roster. He rubbed Woods’s face in his absence and undercut his highly qualified lawyers’ credibility. (At the next hearing, the following Monday afternoon, Cohen appeared in court.)

For a lawyer, this is the job. We go to war with the client we have, not the client we wish to have. That’s a good thing: We’re all flawed; we all do foolish things. It’s a privilege to fight vigorously for someone regardless of their mistakes, just as we would want to be supported when we err.

But we’re not miracle workers. Trump sent Joanna Hendon, an extremely experienced defense attorney, to represent his interests before Wood and try to prevent the government from getting confidential communications between himself and Cohen. If it can be done, she’s the lawyer to do it. But Hendon cannot change the fact that Trump chose Cohen as his personal attorney in the first place or that he’s already talked indiscriminately about the relationship. Character is destiny.   

Read more from Outlook:

Trump could still have obstructed justice even if he didn’t break the law
Sitting presidents can’t be prosecuted. Probably. I was an FBI agent. Trump’s lack of concern about FBI hacking shocks me.

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