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In Pat Cipollone, Trump finds a lawyer he likes

White House counsel Pat Cipollone has built a bond with President Donald Trump, who fondly calls him “Mr. Attorney.” | Jabin Botsford/The Washington Post via Getty Images

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The new White House counsel is winning over his boss. Critics say it’s because he’s too deferential to the president.

During the 21 months of Don McGahn’s stormy tenure at the White House, he would often tell colleagues, half joking: “It’s a good week if I don’t get called into the Oval.”

Pat Cipollone, McGahn’s successor as White House counsel, doesn’t engage in the same sort of gallows humor — if only because, through what allies say is good personal chemistry with his mercurial boss and critics counter is a willingness to enable his worst instincts, he’s managed to stay on the good side of a president who fondly calls him “Mr. Attorney.”

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In six months on the job, Cipollone has turned the White House Counsel’s Office into a central hub of activity and made himself a constant presence in the Oval Office. A 53-year-old former corporate lawyer with an affable style, he has also made enough of an impression on Trump that the president has begun asking aides for their assessment of the White House’s top lawyer — a sign that, at the least, Cipollone has his client’s attention.

“He has the president’s ear, he’s earned the president’s respect and that allows people in this building not just to survive but to succeed in doing their jobs,” said Kellyanne Conway, a senior adviser to the president.

Cipollone is not one to seek attention — friends note that he is often found on the edge of photographs, as if he were seeking to step outside the frame. He is “a cordial but cut-throat negotiator. You never know what he’s thinking,” said a former client. “He should have been a professional poker player.”

But he has nevertheless been at the heart of the controversies that have gripped the White House since the winter, from clearing a legal path for the president to declare a national emergency on the southern border to shaping the White House’s defiant approach to congressional inquiries. Most recently, Cipollone was among the prominent voices who told Trump he could use his emergency powers to slap tariffs on Mexico — and then, alongside Vice President Mike Pence and Secretary of State Mike Pompeo, he helped shape a last-minute deal to end the showdown.

The centrality of the counsel’s office in White House policymaking is normal, and Cipollone consulted with predecessors in both parties before taking the job. But given the abnormal nature of the Trump presidency, a legal adviser who shows the president the best way to accomplish his goals — when many in his own party are often alarmed by the goals themselves — has raised concerns, even among some of the president’s allies.

“One of the best ways to act as a restraint is to raise legal concerns or to play up the economic or political consequences of a decision,” said a former White House official, who noted that McGahn often did so, to the president’s chagrin.

Cipollone’s traditional approach to the job stands in sharp contrast to that of his predecessor, a rumpled election lawyer who didn’t gel with Trump, and who focused almost exclusively on judicial nominations and deregulation. McGahn, who departed in mid-October, frequently dispatched deputies to policy meetings and was rarely present when issues finally reached the president’s desk.

That gave hard-charging aides who happened to be lawyers like the former White House staff secretary, Rob Porter, an opportunity to build outsized portfolios and assume some of the traditional legal responsibilities of the counsel’s office.

Don McGahn

Former White House counsel Don McGahn used to half-joking tell colleagues that “it’s a good week if I don’t get called into the Oval.” | Saul Loeb/Getty Images)

“With this president, it’s not about what the org chart looks like, it’s about how close you are to the president. But Don didn’t care about that,” said a White House official. “For Don it was, ‘I’m going to get my judges done and I’m going to make no friends in the process. I don’t care whether the president thinks I am his guy.’”

As a young lawyer in the 1990s, Cipollone worked as an all-purpose adviser and speechwriter in the attorney general’s office during Attorney General Bill Barr’s first stint on the job. The two share an expansive view of executive authority — one they say is simply a reflection of the Constitution, but that critics charge gives the president too much power. Cipollone has expressed that view in a series of letters to congressional investigators — telling them, in effect, to pound sand.

But while Barr is known among friends as “The Buffalo” — obstinate, stubborn and immovable — Cipollone’s pals describe somebody softer around the edges and a little more humble.

The son of Italian immigrants, Cipollone grew up in the Bronx before attending Fordham University and the University of Chicago law school. He likes to tell friends that his father, a factory worker, went to “UCLA — University of the Corner of Lexington Avenue,” according to his friend and former colleague Jonathan Missner, the managing partner of Stein Mitchell Beato & Missner, the law firm Cipollone left to join the White House.

The father of 10 children, Cipollone is also a devout Catholic. He left the tony law firm Kirkland and Ellis to serve as general counsel of the Knights of Columbus, a Catholic fraternal organization. Later, he founded, along with Missner, a charity to strengthen ties between Catholics and Israel.

In Washington, Cipollone is part of what many in conservative legal circles jokingly call the “Catholic mafia,” a group of like-minded lawyers and coreligionists who have gained influence in the Trump administration. The others include Barr, Supreme Court justice Brett Kavanaugh, Federalist Society executive director Leonard Leo, and the Fox News host Laura Ingraham, who has praised Cipollone — the godfather of one of her children — on her show several times, calling him a “wildly talented lawyer” and a “pretty cool godfather.”

It was Ingraham who recruited Cipollone to help Trump with debate prep during the 2016 campaign, and the two men “just clicked,” said his friend Thomas Yannucci, a partner at the law firm Kirkland and Ellis who recruited Cipollone to join the firm in the 1990s.

“He’s doing this job because he supported this president from the beginning,” said a former client of Cipollone, noting that he was “one of the few who said he would win even when bad exit polls came in on Election Night.”

Joe Biden

He later interviewed for the position of deputy attorney general, a job that went instead to Rod Rosenstein. But he helped prepare former Attorney General Jeff Sessions for his confirmation hearings and stood out as a particularly effective inquisitor, according to a Sessions confidant.

The Democrats’ seizure of the House of Representatives last November, which quashed any hopes that the administration would pass another piece of significant legislation before the 2020 election, has also made the counsel’s office a renewed locus of activity, unleashing an onslaught of Democratic investigations into everything from Trump’s real estate business to whether he obstructed justice to the impact of his short-lived child-separation policy.

“The battles we had during the first year were tax reform and health care — that was a lot of public policy, not a lot of legal stuff,” said the Federalist Society’s Leo, who spoke personally to the president this winter to recommend Cipollone for the job. “The issues now are much more about the assertion of executive power. Pat has been a very, very important player in helping to frame these things.’”

In contrast to McGahn, who studiously avoided the Mueller inquiry and eventually became its star witness, Cipollone’s office has dictated the course of the legal strategy the White House has adopted to rebuff congressional investigations into the Trump administration, which have taken up much of the oxygen in Washington since the midterms in November.

To Democrats, Cipollone and his colleagues in the beefed up counsel’s office, which has grown to approximately 40 lawyers from a low of about 25, are enablers of a president already disinclined to abide by norms and tradition. Their attempts to fend off congressional inquiries have been characterized as “outrageous” by Judiciary Chairman Jerrold Nadler, “a joke,” in the words of House Speaker Nancy Pelosi words, and as “a massive, unprecedented, and growing pattern of obstruction” by Oversight Chairman Elijah Cummings.

Others described Cipollone’s strategy as the standard posture adopted by previous White House lawyers, who have worked to stonewall Congress with the goal of forcing disputes into the courtroom. Most legal observers say the impasse between the two ends of Pennsylvania Ave. will inevitably takes months, if not years, to resolve — with the 2020 election around the corner.

“White House counsels have generally followed a fairly hostile approach to congressional inquiries touching on White House staff. One of the most hostile administrations in history was the Obama administration,” said Jonathan Turley, a professor of constitutional law at George Washington University. “The Democrats come off a bit like Claude Rains saying that they’re ‘shocked, shocked’ that a White House counsel would defy congress. These same Democratic leaders supported President Obama in a systematic refusal to turn over information to Congress.”

Cipollone and his hard-charging deputy for investigations, Michael Purpura, have articulated this view in a stream of letters to Capitol Hill that have largely relied on the argument that lawmakers have no “legitimate legislative purpose” to subpoena many of the documents they have demanded. This is the claim Treasury Secretary Steven Mnuchin fell back on in refusing to turn over the president’s tax returns, and one of the reasons Cipollone cited when he said the White House would not comply with Nadler’s subpoena for documents to aid in a wide-ranging corruption probe.

Donald Trump

The president’s personal lawyers have adopted the same line in lawsuits filed against Deutsche Bank and Capital One — seeking to prevent the disclosure of a ream of financial documents related to Trump’s business, and against the president’s longtime accounting firm, Mazars. A district court judge knocked down the claim in mid-May, arguing that Mazars was required to comply with congressional subpoenas.

According to Turley, the White House is hoping only to tie up the cases in litigation — perhaps through the 2020 presidential election — not necessarily to win. “They are well beyond the navigational beacons of executive privilege. So, if they go to court they have to anticipate that they will lose,” he said. “The benefits of that strategy are magnified in this case because they general view is that the House leadership wants to run out the clock.”

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Cipollone’s newfound power has raised concerns among some of Trump’s critics within the administration who say the counsel’s office has an important role to play in tying the hands of an impulsive president who has at times displayed little respect for constitutional constraints.

These critics say, in essence, that Cipollone is treating the president too much like a normal client. Rather than shut down some of the president’s most controversial ideas, whether declaring a national emergency on the southern border, imposing tariffs on Mexico or sharply restricting the use of fetal tissue in medical research, he has found acceptable — if controversial — legal pathways for Trump to follow.

Cipollone has not always green-lighted the president’s moves, however. He cautioned against Trump’s decision in late March, for example, to change the administration’s position on the Affordable Care Act and to back a lawsuit seeking the evisceration of the entire law.

“In the law that I practiced with him, he would say to the client: ‘What is your goal? What is the best way to get to that goal? And if you want an off-ramp, let’s take it now, let’s not take it three years from now,’” Missner said. “He never imposed his views on you. But Pat’s a pitbull. He will go and he will win.”

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