“No one knew who he was,” said a person close to Cipollone, speaking on the condition of anonymity to describe a closed-door campaign gathering.
Here was a Washington Everyman, one of the faceless masters of the universe in the capital city who quietly turn the wheels of power, influence, the law and business — pointedly, and by design, without ever generating a headline.
That brief encounter would set in motion one of the more curious pairings in modern American politics, something approaching the knitting of a sinner and a saint. A twice-divorced president with a penchant for extramarital dalliances, name-calling and celebrity magazine spreads aligned with a preternaturally private father of 10 whose great passions trend more to devotional trips to the Vatican and Catholic charitable endeavors.
The impression Cipollone made on the day of Trump’s debate prep — the future president and his team viewed this unknown quantity as a man of discretion, of “judgment, intellect and modesty, not a leaker,” as one attendee put it — would linger. Nearly 2½ years later, Trump would select Cipollone as his White House counsel and more recently as the lead attorney in the impeachment trial that has played out for the past two weeks in the Senate chamber.
Cipollone’s central role in the defense has placed him on televisions screens across America, though he would have preferred it was not so. He’d argued before the trial that cameras should be banned from the chamber. He believed that Trump’s case could be damaged by the re-airing of comments made by the president and acting chief of staff Mick Mulvaney, who’d said at a news conference that the media should “get over it” because quid pro quos “happen all the time” in U.S. foreign policy, according to people familiar with Cipollone’s thinking who spoke on the condition of anonymity to discuss confidential strategy sessions. But keeping cameras out also would have had the effect of maintaining his carefully nurtured below-the-radar profile.
Until Jan. 21 at 1:27 p.m., when Cipollone stepped onto the podium on the second day of Trump’s trial and said, “Thank you, Mr. Chief Justice,” he had never uttered a word recorded by C-SPAN’s ubiquitous cameras. As if to underscore his near-anonymity in Washington, Chief Justice John G. Roberts Jr. initially mispronounced Cipollone’s name — as, at various times, would House impeachment managers Adam B. Schiff, (D-Calif.), Zoe Lofgren (D-Calif.) and Hakeem Jeffries (D-N.Y.). (It’s SIP-uh-loan-ee.) Prior to Cipollone’s name emerging as a contender for Trump’s White House counsel job, he’d never even appeared in the news pages of his hometown newspaper — The Washington Post.
Yet, he was now America’s most visible attorney.
“Pat Cipollone is doing a fantastic job, made easier by the fact that the other side has no case — and it is a Total Hoax,” Trump said Thursday in a email to The Post. “He has been a Great White House counsel.”
Cipollone, who did not respond to interview requests, and Trump came from different universes. The president was born into privilege, the scion of a real estate empire. Cipollone, whose given name is Pasquale, is the son of Italian immigrants of modest means. While Trump was the product of an exclusive Eastern boarding school, Cipollone had attended a conservative institution far from the power centers on the East Coast, Covington Catholic High School in Kentucky. His family had moved to the state from the Bronx when his father transferred to Kentucky for his factory job. (A Covington student is now embroiled in a lawsuit against The Post based on the newspaper’s coverage of his role in a confrontation during last year’s March for Life.)
In temperament and style, Cipollone seemed to be the president’s opposite. At the University of Chicago law school, he’d been known as the quiet one, “not the kind to engage in a lot of huge Socratic debate. Not a particularly outspoken person,” said Melanie Sloan, a classmate.
Early on, he worked at the large firm Kirkland & Ellis, but he took a detour to become a top lawyer at the Knights of Columbus, a Catholic fraternal organization, where he held the title supreme advocate. While there, he filed a brief in a Supreme Court abortion case in support of a Nebraska law that outlawed a procedure dubbed by critics “partial birth” abortion.
The practice, he wrote, amounts to “the killing of a human child during an already occurring live birth.” The high court ultimately struck down the law.
Later, he became a name partner in the D.C. firm Stein, Mitchell, Cipollone, Beato & Missner — which made him a wealthy man. Cipollone earned more than $6.7 million in 2017 and 2018, according to a financial disclosure form filed when he took the White House job.
His recent client list has included the construction giant Bechtel, Sony Entertainment Group and the Recording Industry of America. He also once served on a legal team for Johnny Depp in a lawsuit against one of the actor’s previous attorneys.
Over the years, Cipollone naturally fell in with the city’s circle of well-connected Catholics, like-minded influencers with firm positions on issues such as abortion and same-sex marriage.
“Pat puts biblical perspectives on everything,” said former senator Rick Santorum (R-Pa.). Both men have children who attended the Heights School in Potomac, Md., which is affiliated with Opus Dei, an ultraconservative Catholic institution.
He also forged a deep bond with Leonard Leo, then the vice president of the Federalist Society, the influential conservative legal group that has played a major role in shaping the judiciary. Along with Leo, Cipollone was one of the founders of the National Catholic Prayer Breakfast, formed in 2004 “in response to Saint John Paul II’s call for a New Evangelization,” according to its website.
The friends traveled to Rome together two summers ago and visited the Vatican with a priest from the Catholic Information Center, a D.C.-based educational organization on whose board Leo and Cipollone have both served. Cipollone has also served on the board of the Solidarity Association, an organization that supports Catholic evangelization and education.
Cipollone cares about “religious freedom, the culture of life,” Leo said in an interview.
Leo and Cipollone are close with William P. Barr, who served as President George H.W. Bush’s attorney general and now holds the same post in the Trump administration. Cipollone worked for a time as a speechwriter under Barr in Bush’s Justice Department.
“Pat and Bill come from the school that believes executive power is actually very important to the preservation of individual freedom, because the branch that is most susceptible to abusing the public is the legislative branch,” Leo said. “Since the legislative branch by far is the most powerful of the three branches, there has to be a check from both other branches.”
Cipollone has generally avoided electoral politics, but in 2012 he jumped in to help Santorum’s presidential campaign, flying on small planes with the candidate and one other volunteer. The operation was so stripped down that the high-powered lawyer ended up doing tasks normally handled by pimply interns — grabbing coffee or lunches for Santorum or doing advance work.
“Nothing was beneath him,” said David Urban, a consultant and Republican campaign operative who was the third member of the small campaign team.
In an interview, Santorum said he and Cipollone meshed on most issues but “didn’t always see eye to eye on immigration.” Cipollone urged him to moderate his hard-line tone, hewing to Catholic tenets about helping the poor.
On policy, “Pat’s just not a heavy hand,” said Santorum, who has been a client of Cipollone’s to handle contracts in the years since the campaign. “When it comes to legal [strategizing], he can be a very heavy hand.”
'Strong, silent type'
When Trump was elected, Cipollone again took a step toward politics, angling to become deputy attorney general in the Justice Department headed by then-Attorney General Jeff Sessions. Barr — then in private practice — was among those who recommended Cipollone, according to a person who is close to both men. Santorum and Leo also recommended him.
Cipollone didn’t get the job, a turn of events that irked Barr and other supporters. But he remained on the president’s radar, and in 2018 his name surfaced as possible White House counsel. He wasn’t the only finalist, according to an outside adviser who was consulted on a competition that he described as a photo finish.
“There was a tremendous amount of confidence in both his ability as an attorney and that he brought a lot to the table as somebody who understood the larger conservative project,” the outside adviser said.
Having secured the job, he sought input from Melanie Sloan, his University of Chicago classmate.
“I expressed my surprise that he would want to work in this White House. He just doesn’t see the president as I do,” said Sloan, who is a senior adviser to American Oversight, a nonpartisan ethics watchdog that has been critical of Trump. “I think of Pat as a very moral and ethical guy and a devoted family man. All of these values seem at odds with the president.”
At a White House event the month after Cipollone took the job, Trump told the audience that his new top attorney was the “strong, silent type.”
Yet last autumn, Cipollone — the man who doesn’t make headlines — spoke loudly, blasting out an almost Trumpian bolt that dominated the news cycle. In a brusquely worded, eight-page letter to House leaders, he declared that the White House would not cooperate with the House impeachment inquiry. The inquiry was prompted by allegations of a quid pro quo in which Trump threatened to withhold military aid to Ukraine unless it announced an investigation of a leading political rival, former vice president Joe Biden, and his son Hunter, who held a lucrative seat on the board of a Ukrainian oil and gas company.
“Never before in our history has the House of Representatives — under the control of either political party — taken the American people down the dangerous path you seem determined to pursue,” Cipollone wrote. “Put simply, you seek to overturn the results of the 2016 election and deprive the American people of the President they have freely chosen.”
The defiant approach was cheered by conservative tastemakers.
“Cipollone’s letter lays it straight out: You’re invalid. Illegitimate. The hell with you,” Lou Dobbs said on his Fox Business Network program.
Two days later, 21 of Cipollone’s former law school classmates, who said they represented a wide range of political views, asked him to withdraw the letter, arguing that it “flouts the traditions of rigor and intellectual honesty that we learned together” and that it “distorts the law and the Constitution for other purposes, including cable news consumption.”
But those who are close to Cipollone were not surprised at the content or tenor. Cipollone has a visceral disdain for this House and how it works, according to people who know him well but spoke on the condition of anonymity to describe private conversations.
Internally, Cipollone’s arrival in the White House has, at times, caused friction. He has complained frequently about Mulvaney and questioned his performance as chief of staff, according to multiple officials who spoke on the condition of anonymity to discuss private conversations.
Political instincts questioned
Even some of his allies say he does not share enough information with anyone except the president, because he is too fearful of leaks to the media. During meetings, he often has said he wants to speak with Trump one-on-one after the group leaves, a habit that some White House advisers say has left them out of the loop on what he believes is the correct course of action. White House press secretary Stephanie Grisham has complained repeatedly that he doesn’t keep the communications staff informed.
But publicly the White House has only good things to say about the counsel. “Pat Cipollone has done a masterful job leading the president’s defense team on impeachment and he has widespread support throughout the White House,” Grisham said in a statement emailed to The Post. “The president trusts his counsel on a wide range of issues and counts him as one of his closest advisers.”
Cipollone has proved to be a deft infighter. His powers of persuasion were tested during a fierce debate about whether Trump should release the rough transcript of the phone call with Ukrainian President Volodymyr Zelensky. Communications aides told him it would make things worse for Trump, according to officials involved in the discussions. But Cipollone prevailed.
Even then, it wasn’t an easy path. Cipollone tried to manage the media strategy for the transcript release without involving the communications office, arguing that he would provide the best briefings for reporters and lawmakers. He ended up doing the briefings.
The internecine squabbles did not subside. Some inside the White House viewed him as lacking political instincts and repeatedly giving Trump rosier predictions than other advisers. Several days before the impeachment vote, Cipollone was still telling the president that the House might not vote to impeach him, according to advisers who listened in on the discussions. Others told Trump, “Listen, you’re going to get impeached.” They urged the president not to put stock in Cipollone’s analysis.
The others were right. On Dec. 18, a House vote made Trump just the third president in American history to be impeached.
Cipollone was in line to take the lead at the Senate impeachment trial that everyone knew was coming. But with a client as mercurial as the president, he wasn’t going to get to make all the decisions about who else would be at the defense table.
On Christmas Eve, Trump approached Alan Dershowitz, the famed O.J. Simpson defense attorney and emeritus Harvard law professor, in the buffet line at the president’s Mar-a-Lago resort in Palm Beach, Fla. Trump told Dershowitz that he wanted him to join the impeachment defense team, Dershowitz said in a recent interview.
Dershowitz demurred, telling the president that his wife, Carolyn Cohen, would not be pleased. That sent Trump off to find Dershowitz’s wife elsewhere in the room. The president convinced her, and just like that, Trump had added some star power to his defense team.
The heat of the spotlight
Going into the trial, Cipollone also told officials at the White House that he did not want to appear on television news programs and talk shows during impeachment. Instead, he said, he preferred to defer that task to others, including Pam Bondi, a staunch Trump supporter who recently left office as Florida’s attorney general.
“I always hoped that he would do press,” said Ingraham, who has hosted a Fox News Channel program since 2017. “Many times along the way it was clear to me he had no desire to be a television lawyer. He likes to get his job done behind closed doors.”
But there was no avoiding television last week when Cipollone was the first attorney to take the podium to debate the proposed rules for the trial. He adjusted the microphone. A slender man with graying, exquisitely parted hair, he wore a dark suit and a simple red, striped tie. The Washington Everyman in uniform.
His voice dripping with disdain, Cipollone flung many of his remarks at the president’s main antagonist, Schiff, the California Democrat and lead House manager who had just finished his presentation.
“It’s too much to listen to almost,” Cipollone said, “the hypocrisy of the whole thing.”
He invoked the nation’s founders, saying the trial was “their worst nightmare.”
“It’s a partisan impeachment that they delivered to your doorstep,” he said.
“They’re not here to steal one election,” he said. ‘They’re here to steal two elections.”
He closed by urging senators to “end this ridiculous charade” so “we can go have an election.” With that he clapped his folder shut, punctuating the moment, and walked back to his seat.
Cipollone’s client was an ocean away, communing with some of the world’s richest people at the World Economic Summit in Davos, Switzerland. But Trump was paying attention and wanted a fiery performance, people familiar with the president’s thinking said. Trump had hoped for even more of a flamethrower — someone more like himself.
In the past year, the unassuming lawyer now arguing to keep Trump in office had ensconced himself deep into the volatile president’s inner sanctum.
One of Cipollone’s two predecessors, Donald McGahn, was known for staying in his lane, steering clear of the staffer danger zone that surrounds Trump and that has been a factor in so many White House departures.
“Don was very much focused on the judicial enterprise and deregulation,” said Leo, Cipollone’s friend. “Pat has focused some time on that, but he has broadened his interest areas. He gets himself involved in other things in the building with greater intensity than Don might have.”
Inserting himself in policy matters and palace intrigue carries risk. But Cipollone, who has traveled with Trump more than his predecessors, had staked ground as near as possible to the president.
His friends worry he is playing a little too close to the fire.
Alice Crites contributed to this report.