Pat Cipollone, Trump’s aggressive impeachment defender, could change the presidency

WASHINGTON — While President Trump’s legal team is most publicly associated with Rudy Giuliani’s frequent and bombastic appearances on Fox News, or Jay Sekulow, who has a syndicated daily radio program, it is Pat Cipollone, a deeply private 53-year-old White House counsel who is expected to take the lead for the impeachment trial in the Senate.

This starring role is a major change for a man who has largely flown under the radar during his time in the West Wing, and perhaps a surprising choice for a president who often judges his aides based on their TV appearances.

But now, this low-key lawyer is using a defensive strategy that could end up redefining the power of the presidency. Cipollone’s supporters say he is a quiet professional who is protecting executive privilege and has earned the trust of President Trump. But Cipollone’s detractors say his stonewalling of the impeachment inquiry and other investigations into Trump could do long-term damage to the very institution he is supposed to protect.

“He doesn’t represent the president personally. He represents the office of the presidency and I’m worried that this stonewalling litigation posture is going to significantly end up hurting the office of the presidency,” said Neil Eggleston, who served as White House counsel under President Barack Obama.

Cipollone was named White House counsel a little over a year ago. Despite his position as the top lawyer for the White House and the presidency, there are only a handful of photos of him online and little has been reported about his early life. The air of mystery surrounding Cipollone even extends to within Trump’s orbit. One source close to the president described Cipollone as “not a known entity” and in interviews with officials and the president’s associates about the White House counsel, several mispronounced Cipollone’s name. (There’s a long “e” at the end.)

Jonathan Missner, a partner at Stein Mitchell Beato & Missner, a boutique law firm that Cipollone joined in 2012, said the White House counsel “never wanted attention” and has always kept a low profile.

“He’s been in this job for a year, and there’s still basically very little known about him and you very rarely hear from him or see him on camera,” said Missner, who worked with Cipollone until he became White House counsel, and the pair have remained friends. “This is not by accident. This is Pat."

The privacy Cipollone has maintained may come to a dramatic end in the coming days or weeks if he assumes his expected role in the Senate impeachment trial. And as he seems set to take center stage for Trump’s defense, Cipollone has sparked concerns that his aggressive approach to fighting Trump’s impeachment will do lasting damage.

Cipollone declined to comment for this article, but those who have worked with him say he is highly regarded by both Trump’s personal legal team and by the president himself. “He’s a serious tactician. He’s an aggressive advocate, but measured,” Jay Sekulow, one of Trump’s personal lawyers, said of Cipollone.

And Cipollone has something else that may be even more important than legal acumen in his role as White House counsel for the mercurial Trump. He’s become close with the president in a West Wing that has seen record levels of staff turnover with various high-ranking officials cycling in and out of favor. Multiple sources who requested anonymity to discuss the inner workings of the White House described Cipollone as having a strong relationship with Trump.

“The president sees him as beyond loyal,” one source who has worked for the president said of Cipollone.

Another source close to Trump said Cipollone enjoys an unusual level of trust in many of the varied and, at times, warring factions that make up the president’s world, including Trump’s personal attorney Rudy Giuliani, the president’s son-in-law and adviser Jared Kushner, other family members, friends and conservative media outlets.

“There’s very rarely one person that had credibility with Jared, Rudy, Newsmax, the Trump family, and then Trump,” the source said. “That’s a universe of what? Maybe five people.”

For Cipollone, the path to Trump’s White House began in the Bronx, where he was the son of Italian immigrants. When Cipollone’s father, who was a factory worker, was transferred to Kentucky, the family moved with him. Cipollone later returned to the Bronx for college and majored in economics at Fordham University. He earned his law degree from the University of Chicago in 1991.

After law school, Cipollone clerked for a federal judge. He went on to work in the Department of Justice as an assistant to then and now Attorney General William Barr during the administration of President George H.W. Bush. After Bush left office, Cipollone became an associate at Kirkland & Ellis, a large international law firm headquartered in Chicago.

Cipollone entered Trump’s circle during the 2016 campaign, when he was introduced to the future president by Fox News host Laura Ingraham, who credits the attorney with mentoring her as she converted to Catholicism. Ingraham told C-SPAN in 2005 that Cipollone was her “friend” and “godfather” as well as “one of the most brilliant attorneys in Washington.” Cipollone helped Trump with debate prep during the general election campaign, and a source said Cipollone later did legal work for Trump during former special counsel Robert Mueller’s investigation into Russian intervention in the 2016 election.

According to a source who has worked closely with Trump and Cipollone, the White House counsel’s early upbringing in New York strengthened his relationship with the president. “The president's from Queens. Pat grew up in the Bronx,” the source said. “They’re both these super successful outer borough guys who kind of have that real sense of people and they know when they like somebody.”

Cipollone has told colleagues he believes his working-class upbringing in the Bronx defined his outlook. He also credits his aptitude for legal argumentation to the experience of growing up in a large Italian family. Cipollone now has a big family of his own, having raised 10 children with his wife.

Catholicism has also played an important role in Cipollone’s personal and professional life, according to a friend. In 2004, along with other influential Catholics, Cipollone founded the National Catholic Prayer Breakfast, an annual event in Washington that mirrors the older National Prayer Breakfast and has drawn participation from many prominent political figures.

Cipollone came into the White House counsel’s office just after Democrats took control of the House in the midterm elections of 2018. With the opposition’s newfound power, Cipollone expected investigations, and he beefed up his staff accordingly, nearly doubling the White House counsel’s office. He also sought the advice of predecessors from both parties, and met with top Democrats, including the late Elijah Cummings, who served as chairman of the House Oversight Committee before his death last year. Cipollone also reached out to the two men who later went on to help lead the impeachment inquiry: House Intelligence Committee Chairman Adam Schiff and House Judiciary Committee Chairman Jerry Nadler.

When he met with the opposition early in his tenure as White House counsel, Cipollone’s message was that he was prepared for aggressive congressional oversight and was willing to cooperate. The White House did work with Cummings on some of his oversight efforts, but when the Ukraine scandal emerged and led to an impeachment inquiry, he adopted a more partisan stance.

In fact, one of the strategies that has helped Cipollone’s standing in the White House is deferring to the president in the impeachment process. His decision to give Trump freedom to respond to impeachment as he sees fit has raised eyebrows among some legal experts, but endeared him to the president. “He’s ‘let Trump be Trump,’” the source close to the president said.

The leeway the White House counsel has afforded the president included a bombastic six-page letter Trump sent House Speaker Nancy Pelosi ahead of the impeachment vote last month. That missive was reportedly drafted without input from Cipollone’s office. Daniel Jacobson, who worked in the White House counsel’s office under President Barack Obama, described the situation as extremely unusual.

“This letter that Trump wrote with the all-caps and exclamation points. ... That would never happen in our White House for lots of reasons,” Jacobson said. “It would just never have been the case that nonlawyers would have been allowed to draft a quasi-legal document.”

While Cipollone gives Trump a wide berth, he has offered investigators and adversaries almost zero compromises or accommodation. Cipollone’s most visible move came in early October 2019, when he authored a scathing letter of his own to House Democrats. In it, he criticized the impeachment proceedings for lacking adequate procedural protections of the president’s interests, a deficiency he said made the inquiry “constitutionally illegitimate.” Cipollone informed House Democratic leadership that the entire executive branch would not cooperate with the impeachment inquiry.

When Cipollone’s letter became public, the reaction from the legal community was instant and, for the most part, highly critical. Cipollone was accused of making flimsy legal and constitutional arguments. For instance, the Constitution gives the House the sole power of impeachment and the discretion to make the rules of its own proceedings; it does not impose any specific due process requirements on impeachment proceedings.

Cipollone and other Trump allies see the refusal to cooperate with impeachment-related investigations as part of a defense of the presidential power and privilege against undue partisan pressure, and they bristle in particular at the House’s attempts to learn about discussions with the president himself and House investigators’ refusal to allow executive branch lawyers to accompany witnesses to the Hill and defend against improper disclosures.

Beyond the merits of his arguments for not cooperating with Democrats’ impeachment push, critics in the legal community have also faulted Cipollone for not looking out for the long-term interests of the office of the president. For example, the stonewalling of the impeachment inquiry inspired the second article of impeachment against Trump, which accuses the president of obstructing Congress.

While the source on Trump’s legal team said the situation is “fluid,” Cipollone will take charge of the first article that charges the president with abuse of power, related to his efforts to push Ukraine to investigate former Vice President Joe Biden. Sekulow and Trump’s personal lawyers will address the charge of obstruction.

On that front, the president’s attorneys plan to argue there is a constellation of cases where the Justice Department and Trump’s personal counsel are fighting witness subpoenas and requests for documents related to the impeachment inquiry and other investigations into Trump. Their argument is that Trump isn’t obstructing the impeachment process by declining cooperation. Rather, they say the Trump administration is letting the courts decide how much the president is required to cooperate with Congress, even though the Justice Department is currently arguing the courts do not have the power to hear and decide those cases.

Eggleston, the Obama Whie House counsel, said he doesn’t buy the argument the Trump administration’s noncompliance with impeachment stems from a steadfast belief in the executive privileges.

“The decisions to stonewall are not just because of a view about presidential power,” said Eggleson, who was one of several former White House counsels Cipollone called for advice before taking the job.

Eggleston, who also knows Cipollone from D.C. legal circles, said he believes the White House counsel took this approach because “he’s in a situation where he almost has to take these positions because, the more evidence that comes out, the worse his client looks.”

Along with the broader debate of the legal merits of the Trump administration’s lack of cooperation with impeachment, some critics in the legal community have brought up a more nuanced critique of Cipollone. They suggest the stonewalling and particularly Cipollone’s role in it, risks doing lasting damage to the executive branch.

Matt Miller, a former Justice Department spokesman, said the White House counsel customarily would have restrained the government’s attorneys from pressing cases to the point that, if they don’t go Trump’s way, could establish legal precedents that will ultimately erode executive privilege. “It’s one thing to litigate that at the district court level and lose, and get a ruling that is not necessarily binding,” Miller said. “It is another thing to appeal it to the circuit court and risk a ruling that would bind every future president.”

Eggleston made a similar point and said Cipollone is facing a dilemma as White House counsel. “If they get a ruling out of the D.C. circuit that says that senior advisers to the president can be compelled to testify before Congress, that is a huge change in power between the White House and Congress to the detriment of the White House,” he said.

The Trump team is going into the potential impeachment trial confident of their position. Trump’s lawyers know they have an advantage in impeachment proceedings, thanks to the Republican Senate majority. They would seem to have a similar edge in the related court cases due to a conservative majority on the Supreme Court.

However, Eggleston said he would be careful to bet too much on Senate votes, since it takes just a couple of Republican senators breaking ranks for a procedural question not to go Trump’s way. As for the Supreme Court, he pointed out that justices have lifetime appointments and know that their rulings will apply to presidents from either party.

“People who think they can count the votes on the Supreme Court are really deluding themselves,” Eggleston said. “Pretending you can count the votes on these kinds of issues in the Supreme Court is a dangerous place to be.”