Former Stein Mitchell Partner Touted as White House Counsel Problem Solver

By Andrew Strickler

Law360 (May 22, 2019, 1:58 PM EDT) -- Three years ago, Melanie Sloan had a legal problem and a personal crisis she called one of the most trying of her life. A friend suggested that the D.C. attorney call Pat Cipollone, a long-ago law school classmate she’d known casually and hadn’t talked to in well over a decade.

It seemed an unlikely pairing. Sloan is a vocal liberal and media-friendly activist who had long headed a government ethics watchdog group. By contrast, Cipollone was a respected figure in D.C. conservative legal circles, a devout Catholic who’d spent years in the elite ranks of BigLaw while staying mostly clear of politics and the press.

But Sloan said Cipollone not only remembered her from the University of Chicago, where both got law degrees in 1991, but greeted her “like an old friend.” He quickly agreed to represent her, and eventually dedicated far more time and effort to her case than Sloan said she’d ever expected.

“The most important thing Pat did for me wasn’t his legal work. It was his whole attitude of, ‘Of course I remember you, and I’d be thrilled to help you,’” said Sloan, now a senior adviser to liberal watchdog group American Oversight.

“Even though he knew I was on the opposite end of the political spectrum, it didn’t matter at all, and I don’t think we have that many people in our lives who will go as far and do as much as he did for me," she added.

Unbeknownst to Sloan, her affable, understated lawyer was poised to step onto a turbulent political stage that by October 2018 would lead to his current post — White House counsel to President Donald Trump.

It’s a vaguely defined job, and one historically shaped almost entirely by the political winds of the time and Oval Office occupancy. And while Trump himself revels in shoot-from-the-hip pugilism, colleagues describe the newest White House counsel as a “calming” presence and a forward-thinking tactician always looking for a favorable “offramp” in legal disputes.

And in contrast to many in BigLaw, he’s disinclined to self-promotion and infighting — qualities some of his supporters said will help him stay focused on the law in the notoriously chaotic Trump White House.

“Unlike many people in Washington political life, Pat doesn’t run around town engaging in gossip, he doesn’t push his own image, and he keeps his counsel close to the vest,” said Leonard Leo of The Federalist Society, who has known Cipollone since the early 2000s.

“He’s also an incredibly capable lawyer and a litigator familiar with the thrust and parry of trial practice and the importance of crisis management. Those are all skills I think will serve him as White House counsel.”

The 53-year-old Cipollone is also a political novice compared to his predecessor Don McGahn, a vocal conservative who has given speeches at Federalist Society, worked for the National Republican Congressional Committee and sat on the Federal Election Commission during the George W. Bush administration.

Ed Whelen, a conservative legal activist and president of the Ethics and Public Policy Center in D.C., said he first crossed paths with Cipollone at the U.S. Department of Justice in the 1990s, and has known him personally since.

"Knowing who will connect with the president is tough to figure out, but Pat is a very likable, extremely savvy guy, and I think that his personal qualities and his legal experience will more than make up for his limited executive-branch experience," Whelen said.

But Cipollone is also no stranger to Trump World. By mid-2016, he was quietly helping to prep the then-presidential candidate to debate Hillary Clinton. And he continued after the election as a behind-the-scenes adviser for Trump’s legal team amid the Mueller investigation.

By the time he stepped into the White House counsel job, the administration was braced for the Mueller report and faced an onslaught of criminal and congressional investigations.

At least on paper, Cipollone appears to have fully joined the fray. In recent days, he put a determined voice behind the White House’s broad rejection of congressional demands for records and testimony from current or former executive office members.

In a lengthy letter, Cipollone called the requests from the House Judiciary Committee “unmoored” from any articulated legislative purpose and an attack on the foundations of executive privilege and the separation of powers.

“The White House will not participate in the committee's ‘investigation’ that brushes aside the conclusions of the Department of Justice after a two-year-long effort in favor of political theater pre-ordained to reach a preconceived and false result,” he said.

Committee Chairman Jerry Nadler in turn said the president wanted to “make himself a king” and unaccountable to any oversight.

Cipollone’s road to the White House began in Kentucky, where he went to Covington Catholic High School — the same private boys school that was in the headlines early this year after a video of a confrontation between students at a pro-life march and a Native American went viral.

After graduating in 1984, Cipollone headed to Fordham University in the Bronx and the University of Chicago Law School, where he was managing editor of the law review.

Cipollone also clerked for U.S. Court of Appeals Judge Danny Boggs of the Sixth Circuit. Judge Boggs, now on senior status, was a Reagan nominee who had been deputy secretary of energy in that administration.

Still in his mid-20s, Cipollone had a taste of federal government service in a short stint as an assistant to Attorney General William Barr. He joined Kirkland & Ellis as an associate in D.C. in 1993.

Kirkland partner Thomas Yannucci, who recruited Cipollone to the firm, described the young lawyer as smart, hardworking and unusually adept at dealing with powerful people.

“We could have a client, a CEO or a general counsel come in, and they would really talk to Pat,” Yannucci said. “He just has a way with people, he's got great judgment, he's respectful. I think their feeling was, 'Here's a guy who's nuanced and just gets it.' In that sense, he was advanced compared to a lot of his peers."

While at Kirkland, Cipollone developed into a highly successful commercial litigator, eventually representing mega-companies like General Motors in product-related cases and defending Bechtel Corp. in suits brought by contractors.

Cipollone, who has long been active in Catholic charities, took a sharp career turn in the mid-1990s, becoming general counsel for The Knights of Columbus, a Kirkland client. The Catholic fraternal organization has a sizable insurance business and was embroiled at the time, along with many in the industry, in so-called “vanishing premium” class actions.

"He believed in their mission and was already a Knight, and he wanted to support them," Yannucci said.

Cipollone returned to D.C. and Kirkland in the fall of 2001, but left again in 2012 to become a named partner at Stein Mitchell, a storied white collar and litigation boutique co-founded by Jake Stein in 1965.

Stein became nationally known in the 1970s as the only lawyer who won an acquittal for a client in the so-called “Watergate Seven” trial, and was long considered a leader of the D.C. legal community. He died in April.

Cipollone "is hard to pigeonhole, and a bit of a populist in terms of his views,” Yannucci said. “He's not someone who thinks every lawsuit is frivolous, and there were times where he wanted to be on the other side of the table with a plaintiff, and that can be hard when you're in BigLaw."

Stein Mitchell managing partner Jonathan Missner said the firm had given Cipollone a new opportunity to represent “both massive companies and the little guy in the fight.”

“Pat just adored Jake, he loved that Jake was a ‘lawyer’s lawyer,’ and a guy who really stood for justice,” Missner said. Stein Mitchell Cipollone Beato & Missner became Stein Mitchell Beato & Missner upon Cipollone’s departure.

Outside of a busy work and family life — Cipollone and his wife Becky live in suburban Washington and have 10 children — he’s also served on the boards of a number of Catholic-affiliated organizations. They include the Sanctuary of Culture Foundation, which supports the Vatican library, and the Catholic Information Center in D.C. Cipollone is also credited with helping start the annual National Catholic Prayer Breakfast.

In 2017 and 2018, Cipollone made $6.7 million at Stein Mitchell, according to his federal financial disclosure forms. By comparison, McGahn was making $179,700 as White House counsel, the top pay for White House employees as of mid-2018.

Cipollone also has close ties to conservative pundit and Trump loyalist Laura Ingraham, who reportedly recommended him to the campaign. In a 2005 interview, Ingraham described Cipollone as her godfather and a key factor in her conversion to Catholicism.

One of Cipollone’s daughters has also worked as a Fox News booker for Ingraham’s show. Cipollone also represented Ingraham in recent years at Stein Mitchell, along with name-brand media companies like Sony Entertainment Group and Warner Music.

Attempts to reach Cipollone were not successful. The White House press office did not reply to a request for comment.

Missner and others declined to comment on Cipollone’s political views or how he might maintain a working relationship with Trump, whose recent relations with McGahn could most charitably be described as strained.

Cipollone’s ability to find the middle ground is being tested. Tensions this week over Trump’s pledge to fight all subpoenas were again raised when Cipollone told the House committee that McGahn enjoys “absolute immunity” from congressional subpoena, and had been directed not to appear at a hearing Tuesday.

Missner did say generally about Cipollone that “if there is a way to settle and negotiate an issue quickly and creatively to the benefit of the client, he’s going to be the first person to say ‘let’s do it.’”

But that’s only part of what makes Cipollone a good lawyer, Missner added.

“What makes him effective is that people know that if the early solutions don’t work out, he knows how to skillfully fight and is always willing to do so,” he said.

--Editing by Philip Shea and Rebecca Flanagan.

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