Lawyers who know Trump's legal team told me what they really think of them

Landing the President of the United States as a client is usually the sort of thing that lawyers would crawl over broken glass to add to their resumés.

When Bill Clinton faced a lawsuit over allegations of sexual harassment while governor of Arkansas, a long-running independent counsel investigation into his pre-White House conduct, a House impeachment inquiry and a Senate trial, the lawyers who rose in his defense had long held places in the top echelons of the Washington DC legal community. These were bold-faced figures such as Robert Bennett, former Senator Dale Bumpers, and David Kendall, who brought the resources of a top law firm, Williams and Connolly, to augment the work of Charles Ruff and Cheryl Mills in Clinton's White House Counsel's office.

But since Donald Trump took office in 2017, being the president's lawyer is a gig most high-powered Washington attorneys have tried to avoid like the plague.

Though he became the subject of what would be a two-year investigation conducted by former FBI Director Robert Mueller within his first six months in office, a lifetime of walking away from legal bills and disregarding legal advice meant he was unable to secure the services of any of the eminences grises of the legal establishment.

Instead, the men charged with representing the president in the Trump era make up one of the motliest crews in the annals of American jurisprudence.

His first personal attorney, Michael Cohen, now spends his days in a federal prison cell in upstate New York after pleading guilty to committing campaign finance crimes at Trump's behest. The man who now styles himself as Trump's personal attorney, former New York City mayor Rudy Giuliani, is now reportedly the subject of a Justice Department investigation of his own after two associates were indicted for other campaign finance crimes.

And while Trump has been able to attract some Washington legal graybeards like John Dowd and Ty Cobb to his cause, they didn't last long. Those who did, such as former White House Counsel Don McGahn, ended up leaving rather than do the "crazy s**t” Trump asked of them.

So when it came time for Trump's legal team to take to the Senate floor in his defense, the men and women who assembled at the purpose-built "impeachment table" on the Republican side of the Senate floor were more The Bad News Bears than the 1992 Dream Team.

Veteran litigators say the haphazard team that the White House has assembled is in stark contrast with the arguments offered by lead House manager Adam Schiff, a former prosecutor, and his colleagues.

Ted Boutrous, the Los Angeles-based co-chair of litigation at Gibson Dunn (where Schiff got his start as an attorney) told me the California congressman and his colleagues had hit the ball out of the park.

"If this were a bench trial, the chief justice would rule in favor of the managers' case and against Donald Trump in a second based on this record," he said when I spoke to him after the House managers had concluded their third day of opening remarks.

"I don't know how any reasonable judge or lawyer could watch that, hear the evidence, see the evidence and come out any other way," he added.

Boutrous stated that he has been "enormously impressed" with the way each of the House managers have contributed to the case.

By contrast, he said the president's lawyers’ performance on Saturday was just as "depressing and embarrassing" as the House managers' presentation was "impressive and inspiring."

"From a lawyer’s perspective, it was so far below what you would expect of any good lawyer, let alone lawyers who are supposed to be representing us all in a sense — they're supposed to represent the President of the United States," he said. "Whatever you think about the merits, at least put on a good-faith factual case that isn't filled with misstatements, follows the evidence and addresses the law."

Trump's attorneys "ignored all of the damning evidence and the main allegations behind the impeachment articles and instead sought to distract with disinformation and irrelevant arguments about the Mueller report and FISA," he said, adding later that Trump's lead private counsel, Christian Advocates for Serving Evangelism founder Jay Sekulow — an experienced Supreme Court litigator in his own right — appeared to be acting as if the Senate proceedings were a game or a radio talk show, rather than a courtroom.

"It's like there's a mania that has taken hold of some of these people, and these lawyers that are not adhering to the standards that we all have adhered to over the years. And they're doing it on the biggest stage imaginable," he said.

White House Counsel Pat Cipollone fared no better in Boutrous' assessment, particularly since several statements he made in the course of his presentation on Saturday bore no relationship to reality.

"Cipollone was making a ridiculously, provably false point when he said that Republicans weren't allowed into the SCIF during depositions. That will get you sanctioned," he said.

Another veteran civil litigator with Supreme Court experience, who did not want to be identified for ethical reasons, had similarly harsh words for Sekulow's performance, particularly the embarrassing gaffe he committed on Tuesday when he misheard Rep. Val Demmings speak of "FOIA [Freedom of Information Act] Lawsuits" and immediately began shouting in response about "lawyer lawsuits."

"That thing about the 'lawyer lawsuits' — what was that? He wasn't being attentive, and then to make matters worse, he made it into a huge rhetorical yelling thing that was just wrong," the lawyer said. "Do you know how humiliating that would be? You would go home and cry yourself to sleep, but he [Sekulow] just moved on and went back in front of the cameras."

"I had always thought of him [Sekulow] as sort of a clownish, weird figure," the attorney continued. "He had those cases in the Supreme Court, those religious freedom cases and he was always a bit of character, but in the Supreme Court you can't get away with not doing your homework, not being respectful, and not knowing the law or saying false things and misleading."

But former Watergate prosecutor Nick Akerman, who is currently a partner at Dorsey and Whitney in New York, said recent reports that John Bolton, Trump's ex-national security adviser, wrote in his forthcoming book that Trump told him the release of aid to Ukraine was linked to an announcement of investigations into Joe Biden — the "quid pro quo" for which Trump was impeached — mean the president's lawyers may have bigger problems than simply embarrassing themselves on TV.

"They are all witnesses, right in the middle of everything," Akerman said of Cipollone and his colleagues in the White House Counsel's Office. "They shouldn't even be representing Trump since they're the ones that basically are right at the core of his whole obstruction of Congress."

Akerman said that if Bolton told multiple National Security Counsel staffers to "talk to the lawyers" about the "drug deal" being put together by White House Acting Chief of Staff Mick Mulvaney and Ambassador to the EU Gordon Sondland, that may mean the entire counsel's office has a massive conflict. If this did indeed happen, then what is worse for them are the "knowingly false statements" made by Cipollone and others who argued in legal papers and on the Senate floor that Trump never linked the release of aid to Ukraine to investigations.

"The biggest concern these guys are going to have is that their credibility is completely blown," he said. "Who is going to believe them now? They have zero credibility at this point. If you're a trial lawyer in front of a jury, and the jury believes you're a liar, you've got nowhere to go. You might as well just head for the hills."