When Pat Cipollone steps foot onto the faded blue carpet of the Senate chamber next week, the relative anonymity he has enjoyed for much of his three-decade law career will be stripped away by the glare of cameras and the scrutiny of history.
But President Donald Trump’s White House counsel, who is expected to lead his defense during the country’s third-ever presidential impeachment trial, will have more to confront than the 100 senators serving as jurors. Cipollone will face twin, and perhaps competing, demands on his performance from a President obsessed with production value and from a Senate dynamic that may reward the most measured display.
Trump’s desire for a prime-time-worthy drama to clear his name is set to collide on Tuesday with the reality of a defense helmed by someone with little experience in the spotlight.
A litigator and plaintiff lawyer for much of his career, Cipollone is described by people who know him as always well-prepared and even-keeled – traits that colleagues and friends say will guarantee he arrives on Capitol Hill armed with an airtight legal argument, but that don’t guarantee the kind of telegenic representation Trump has sought in the past or privately said he wants in his trial.
Focusing on substance
While few, if any, lawmakers in either party believe Trump’s symbolic day in court will end with anything but an acquittal, a strong defense from Cipollone and the deputies expected to assist him could bring the trial to an earlier close – especially if the Republicans who are unsure about calling witnesses find that the White House’s arguments settle their remaining questions about the case.
Cipollone has spent weeks preparing for the trial. A rotating cast of House Republicans involved in the lower chamber’s impeachment proceedings have trekked down Pennsylvania Avenue to brief Trump’s lawyers on the case. Aides have choreographed a two-pronged strategy that will feature different supporting characters for the pair of arguments against each article of impeachment, with the supremacy of executive power at the heart of both defenses. And Cipollone has been updating the President regularly about the evolution of his defense.
Jay Sekulow, one of Trump’s personal lawyers and someone who brings a wealth of TV experience, is expected to assist Cipollone in presenting the case.
Cipollone is expected to deliver the opening argument in the trial, while Sekulow is expected to present an overview of the “entire process” surrounding impeachment, sources close to the legal team said.
“Pat has tried cases with billions of dollars at stake and had taken cases to jury verdicts involving tens of millions of dollars,” Sekulow told CNN. “He knows how to communicate to an audience. He understands the nuance of the Senate.”
Two of Cipollone’s deputies, Pat Philbin and Michael Purpura, are also expected to play supporting roles on the President’s public defense. Ken Starr, the former independent counsel whose work led to the impeachment of Bill Clinton, will present arguments on the Senate floor alongside Robert Ray, his successor at the Office of Independent Counsel, and Alan Dershowitz, a constitutional lawyer. The White House is also expected to put additional attorneys on the floor – including Jane Raskin, one of several lawyers brought on to bolster Trump’s legal team during the special counsel’s probe last year, and Pam Bondi, the former Florida attorney general who has been helping the White House with communications behind the scenes.
White House officials say Cipollone’s background uniquely prepares him for the challenge of connecting with both the senators in the room and the regular people watching at home. Born to Italian immigrants, Cipollone rose from humble beginnings in the Bronx and worked in factories, on construction sites and at McDonald’s, where he flipped burgers and advocated for his fellow workers to unionize.
He went on to Fordham University, graduating as valedictorian, and eventually attended law school at the University of Chicago. Cipollone later clerked for a Sixth Circuit Court of Appeals judge and went on to practice civil litigation. Throughout his career, Cipollone – whose given name is Pasquale, which he shortened to Pat – has been active in the Catholic community; he and his wife have 10 children.
Rising stock amid impeachment
Cipollone’s relationship with Trump has long been reinforced by the fact that he shares the President’s sweeping view of executive authority.
In a now-infamous letter to Congress on October 8, Cipollone echoed the fiery language of his boss but expressed sentiments with which he agrees: that the executive branch has the right to deny Congress access to testimony, for example. That eight-page missive established the White House’s official position of refusing to cooperate with the impeachment inquiry, which persisted throughout the House’s months-long proceeding.
Nearly two dozen of Cipollone’s former law school classmates signed onto a letter to him in October, urging the White House counsel to disavow his message.
“We are sorry to see how your letter to the congressional leadership flouts the traditions of rigor and intellectual honesty that we learned together,” the 21 former classmates wrote. “When any President openly invites the help of foreign powers for partisan political purposes, Congress in the exercise of its constitutional powers should conduct an inquiry and the White House should cooperate…Your letter instead distorts the law and the Constitution for other purposes, including cable news consumption.”
Josh Davis, director at Goulston & Storrs and a former law school classmate of Cipollone’s at the University of Chicago, said he finds Cipollone’s handling of the impeachment saga “profoundly disappointing” despite the respect he had for his fellow law student when they met.
“My memories of Pat are that he was a very smart, careful person with whom I often disagreed but who I had great respect for,” Davis, who signed the letter to Cipollone in October, told CNN. “He was good on his feet in law school classes, he was prepared and said smart things.”
Slowly since joining the Trump administration in December 2018, and more rapidly since the impeachment inquiry started, Cipollone has developed a warm relationship with the President and has consolidated power within the West Wing. His stewardship of the White House’s response to impeachment – and other recent, high-profile contributions, such as performing the legal review of the White House’s decision last month to take out a top Iranian general – has elevated his position internally.
White House officials say Cipollone built the counsel’s office like a law firm, hiring lawyers with specialized experience and preparing from the day he started, which was soon after Democrats won control of the House, for the likelihood that Trump would one day face impeachment.
Cipollone has also benefited from his close alliances with people across the spectrum of Trump’s eclectic inner circle. His decades-long relationship with Attorney General Bill Barr, people familiar say, gave him credibility in the President’s eyes when he started on the job. Both Barr and Cipollone are Catholics, and Cipollone grew close to the attorney general when he worked for him as an aide and speechwriter the first time Barr held the job, during the George H.W. Bush administration.
Fox News host Laura Ingraham is also a longtime friend of Cipollone’s; his daughter has worked on her prime-time show in Washington. The fiery conservative host helped bring Cipollone into Trump’s circle long before he ascended to the White House counsel role.
Cipollone even helped Trump with debate preparations during the 2016 campaign, alongside Ingraham, a person familiar with the sessions said. At the time, Trump’s first White House counsel, Don McGahn, was the top lawyer on the campaign.
Debuting his style
Cipollone’s presentation before the Senate will be watched as much for the way he delivers it as for the arguments he outlines. Trump has wavered for weeks over the type of trial he would support publicly, but privately he has long craved a robust defense aimed at vindicating him.
Cipollone – someone Trump has described as the “strong, silent type” – has no experience on television and little in the public eye.
Jonathan Missner is a friend of Cipollone’s and partner at the law firm, Stein Mitchell Beato & Missner, that Cipollone left to take the White House post. He said Cipollone has never been one to seek the spotlight.
“He’s got a very calming personality. I don’t think he yells. I don’t think he gets rattled easily,” Missner told CNN. “He’s quick off his feet. He doesn’t need to be the center of attention and he doesn’t want to be the center of attention, and he doesn’t need credit for anything.”
“There are so many lawyers who want attention,” he added. “So, it’s ironic that he’s the guy that’s doing it.”
Cipollone has been walking through his prepared arguments with aides during sessions at the White House. His team has pored over documents related to the Clinton and Nixon cases, and he honed the White House’s central argument by crafting the trial brief due to Congress by noon on Monday. Trump’s legal team previewed the aggressive tone they will strike in the trial on Saturday evening when they filed a response to the Senate’s summons, denouncing every aspect of the articles themselves and the procedures followed in the House.
Cipollone huddles in his office each morning with top White House officials, including acting chief of staff Mick Mulvaney and legislative affairs director Eric Ueland, to strategize on aspects of the case.
White House officials note Cipollone has tried cases as a litigator, claiming his time in the courtroom has taught him to keep an audience’s attention and weave catchy arguments as well as any television experience could.
“Presenting to debate requires [a] unique combo of skills that Pat has in spades,” Ueland told CNN. “Members like him, trust him and respect him and look forward to him leading the President’s defense on the Senate floor.”
Ueland said Trump “made it emphatically clear” by tapping Cipollone to lead his defense that “he trusts him, respects his abilities and counts on him to deliver in the US Senate.”
“He’s a trial attorney, not some academic or corporate lawyer who has only done contracts or real estate deals,” said another administration official, who argued it is a “misconception” that Cipollone’s inexperience on the airwaves will be a hindrance.
White House officials at one point considered adding one or more House Republicans to give the defense more teeth, but Senate Majority Leader Mitch McConnell and others advised against the idea. Trump’s fixation on having his fiery conservative allies go to bat for him on the Senate floor underscored how badly he wanted to see a fight on his behalf.
Dershowitz, a lawyer Trump personally persuaded to join his defense team, Sekulow and Bondi have all proven themselves adept performers over years of cable news appearances. Their presence on the team could add dramatic flair to the presentation, reflecting the President’s desire for a theatrical defense.
Although multiple sources said Cipollone, Sekulow, Philbin and Purpura have carefully laid out plans for the defense, even the senators who will ultimately decide Trump’s guilt or innocence don’t know exactly how the trial will unfold – leaving room for twists in the process to alter Cipollone’s course.
Missner, the former law partner who started a Catholic charity with Cipollone, suggested the White House counsel wouldn’t be rattled.
“He’s one of these people – and I don’t know many people like this – that are capable of thinking 10 steps ahead,” Missner said. “All the time.”