WASHINGTON — As a lawyer in private practice, Pat A. Cipollone, now President Trump’s White House counsel, told colleagues that there were two approaches to legal fights.
One, he said, was like the Department of State, when the two sides would try to work out a deal to avoid painful and expensive litigation. The other, when the first failed, was the Department of War.
As of this week, Mr. Cipollone has put himself squarely in the war camp when it comes to Mr. Trump’s defense against the House impeachment inquiry. After earlier advocating that the president adopt a policy of transparency by releasing the document at the heart of the impeachment debate — the reconstructed transcript of Mr. Trump’s call with his Ukrainian counterpart — Mr. Cipollone has shifted course and is now leading a no-cooperation strategy that holds substantial political risks but also seems to suit his combative client in the Oval Office.
It is a role that has pushed Mr. Cipollone, 53, to the center of a battle that could determine the course of Mr. Trump’s presidency and potentially lead to a constitutional battle with far-reaching ramifications. In building an argument that Mr. Trump has no obligation to respond to demands for information from Congress, Mr. Cipollone, in a letter sent Tuesday to House Democratic leaders, laid out an extraordinarily broad view of executive authority that, if maintained, seems likely to be viewed skeptically by the courts.
“Pat’s taking a leading role in this proceeding because of the institutional interests that are at stake,” said Jay Sekulow, Mr. Trump’s personal lawyer. “He’s the right man for the task. He has the right temperament and disposition.”
Rudolph W. Giuliani, another of Mr. Trump’s lawyers and a key player in the Ukraine affair, heaped praise on Mr. Cipollone. “From a lawyer’s point of view, the letter is close to brilliant,” he said.
But to critics of Mr. Trump, Mr. Cipollone is seeking to twist the law and stonewall an entirely legitimate inquiry from a coequal branch of government and undercut the ability of Congress to pursue its constitutionally mandated remedy of impeachment.
“I cannot fathom how any self-respecting member of the bar could affix his name to this letter,” George Conway, a constitutional lawyer and the husband of Kellyanne Conway, a top aide to Mr. Trump, said on Twitter. “It’s pure hackery, and it disgraces the profession.”
Mr. Cipollone’s defiant posture toward Congress, Democrats said, was more about political positioning than a serious effort to articulate a legal and constitutional defense for Mr. Trump.
“They’re taking a position that seems to me to be quite frivolous: that Congress doesn’t have any power to investigate most of what they’re investigating,” said Neil Eggleston, who was the White House counsel in the Clinton and Obama administrations. “It’s sort of a last refuge.”
A well-known figure in Washington’s community of Catholic conservatives and anti-abortion activists, Mr. Cipollone came to the White House late last year after earlier having helped prepare Mr. Trump for the presidential debates in 2016 and advised his legal team during the special counsel’s investigation into Russian interference in the campaign.
But Mr. Cipollone generally keeps such a low public profile that even those who have known him for years differ on how to pronounce his last name (it is sip-uh-LOAN-ee). He drives a pickup truck and a Honda Pilot, into which he loaded a beloved desk chair for the move to the White House after his appointment last December.
He has contributed substantially to Catholic charities and causes, but his political work has been largely behind the scenes, including his former law firm’s defense of former Gov. Scott Walker of Wisconsin in a campaign finance case.
The son of an Italian-born factory worker and homemaker, Mr. Cipollone spent much of his childhood in the Bronx. After his father was transferred to Kentucky, Mr. Cipollone attended Covington Catholic High School before returning to New York to attend Fordham University.
A debate champion and intramural athlete, he worked days in Fordham’s computer center and summers in construction, factory and clerical jobs. He was the class of 1988’s valedictorian, graduating first in a class of 650 with a degree in economics and political philosophy. Already interested in constitutional law, he wrote a senior thesis on “Substantive Due Process and the 14th Amendment.”
Mr. Cipollone won a full academic scholarship to attend the University of Chicago Law School. There, he sank deep conservative roots, helping lead a student chapter of the Federalist Society.
Mr. Cipollone served a clerkship with Judge Danny Julian Boggs, a Reagan appointee, on the Sixth Circuit Court of Appeals.
As part of the interview process, Mr. Cipollone took the judge’s famously difficult “general knowledge” quiz, which he used to gauge knowledge beyond the law. In Mr. Cipollone’s year, potential clerks had to answer 64 questions, including, “What was the Trail of Tears?” “What did the battles of Actius, Lepanto and Salamis have in common?” and “When and what was the Edict of Nantes?” (Judge Boggs said he had looked back in his files and could not find Mr. Cipollone’s score.)
Judge Boggs recently had lunch with Mr. Cipollone in the White House mess. “I complimented him on not seeing his name in the paper,” the judge said, “which means he’s doing a good job.”
Mr. Cipollone went from Judge Boggs’s chambers in Louisville to Washington, and a speechwriting job with William P. Barr, who was attorney general in the George Bush administration and was named attorney general by Mr. Trump a few months after Mr. Cipollone arrived at the White House.
A fellow clerk, Jennifer Hall, recalled sitting in Judge Boggs’s bookshelf-lined chambers between Mr. Cipollone and another clerk, Stephen Vaughn, now a trade lawyer in Washington. “They would yell at each other over me,” she recalled, “listening to Rush Limbaugh.”
Mr. Cipollone and his wife, Rebecca Cipollone, have 10 children. The youngest is a 10-year-old son and the oldest a 26-year-old daughter, who works at Fox News for Laura Ingraham, the conservative commentator, who was introduced to Catholicism by Mr. Cipollone.
Mr. Cipollone is a founder of the National Prayer Breakfast, participates in the anti-abortion March for Life, and events that draw Washington’s Catholic elite, like the Red Mass, celebrated each year at St. Matthew’s Cathedral on the Sunday before the Supreme Court session begins. (Mr. Cipollone was absent when the event was held this past weekend.)
After his stint with Mr. Barr, Mr. Cipollone joined the law firm Kirkland & Ellis in Washington. In the mid-1990s, he moved his family to Connecticut and took a job as general counsel for a Kirkland & Ellis client, the Knights of Columbus, a Catholic fraternal organization and multibillion dollar insurance company. He later rejoined the firm, then left for a partnership at Stein, Mitchell, Cipollone, Beato & Missner, where he worked on Mr. Walker’s case, among others.
Melanie Sloan, a law school classmate who works with the liberal watchdog organization American Oversight, said she called Mr. Cipollone for help in a complicated legal matter after classmates recommended him. “He was kind and happy to help me,” she said. “I don’t feel like too many people in Washington would take a call from somebody they haven’t been in touch with 20 years and be right there to help. And I never got a bill.”
Mr. Cipollone earned nearly $7 million at Stein Mitchell in 2017 and 2018, according to his White House financial disclosure report.
“With every client, with everybody he sat in front of, he used the term ‘off ramps,’” says Jonathan Missner, a partner of Mr. Cipollone’s at the firm. “That’s Pat. He looks for off ramps, and he’s good at it.”
It is also true, he said, that Mr. Cipollone “can be a pit bull — and that’s the Department of War.”
Michael Crowley and Sharon LaFraniere contributed reporting. Kitty Bennett contributed research.
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