Democratic lawmakers at the impeachment trial said on Tuesday that Cipollone "played an instrumental role" in that obstruction and argued that his representation of Trump threatens to undermine the integrity of the proceedings.
The Democratic-led House of Representatives has accused Trump of undertaking an unprecedented campaign to prevent them from probing allegations that he withheld military aid and a White House meeting to pressure Ukraine to investigate a political rival, former Vice President Joe Biden. They have charged Trump with abuse of power and obstructing their probe, while he has proclaimed his innocence.
One of the main pieces of evidence to support the obstruction charge is a widely criticized letter written by Cipollone on Oct. 8 in which he said Trump could not permit the administration to participate in the Ukraine investigation, which he described as an illegal attempt to remove a democratically elected president.
Cipollone's letter thrust the lawyer to the forefront of the administration's battle against the impeachment inquiry in the House of Representatives, bringing him public attention that friends and colleagues say he has long eschewed, unlike many of Trump's lawyers.
On Tuesday, the camera-shy Cipollone, 53, was in a much brighter spotlight as the televised trial got under way in the Republican-led Senate, where he is helping to lead the Republican president's defense.
The arguments and political tone in his Oct. 8 letter, uncharacteristic for a White House counsel, drew rebukes from many legal experts, including former law school classmates, who said it distorted the law for cable news consumption.
While Cipollone declined to comment for this story, Jay Sekulow, another leading member of Trump's legal team, said Cipollone's arguments were "exactly what the founders had in mind in crafting a constitution that respects separation of powers."
In a letter to Cipollone on Tuesday, Democrats urged him to disclose the full extent of his knowledge of Trump's Ukraine activities and said evidence suggested his office had been directly involved "in potential efforts to conceal President Trump's scheme from Congress and the public."
In a statement, the White House dismissed as "ludicrous" the demand that Cipollone turn over confidential information and "absurd" the idea that he could not represent Trump effectively.
'RARE COMBINATION'
While Trump was at his Mar-a-Lago resort in Florida for the Christmas holidays, Cipollone was in his second-floor White House office - where he has a photograph of his family, including his 10 children, with the president - working on his trial arguments on a yellow legal pad, according to a person familiar with his preparations.
"He's going to give a thoughtful, substantively sound presentation," U.S. Secretary of Labor Eugene Scalia, who attended the conservative-leaning University of Chicago Law School with Cipollone, said in an interview.
Cipollone is "a rare combination of law review smart and street smart," said Scalia, who was editor-in-chief of the law school's legal journal when Cipollone was on staff.
On Tuesday, Cipollone took the podium at the Senate trial for the first time, calling the impeachment charges "ridiculous" and asserting that Trump had done "absolutely nothing wrong."
Cipollone said the Democrats had no case. "They're not here to steal one election, they're here to steal two elections," Cipollone said, a reference to 2016 when Trump won the election and to November 2020 when he is seeking reelection.
Cipollone, who became White House counsel in December 2018, was introduced to Trump by conservative television host Laura Ingraham in 2016, when he was a partner at a boutique Washington law firm. He helped Trump prepare to debate his then-Democratic election opponent, Hillary Clinton.
Ingraham, in an interview, described Cipollone as a devoted Catholic who is calm and methodical and a spiritual mentor to her. She said he was not a "showboat."
Cipollone is the son of an Italian factory worker who named him Pasquale. He goes to mass often, perhaps as often as every day, according to a person who knows him, and participates in the annual March for Life in Washington that protests abortion.
Jonathan Missner, managing partner of Stein Mitchell Beato & Missner, the firm Cipollone left to join the Trump administration, noted that Cipollone spent his early years in the Bronx in New York City, where he was raised to prize loyalty and trust. "Pat's very loyal to his clients," Missner said.
In his Oct. 8 letter to the House leadership, Cipollone appeared to demonstrate that loyalty to Trump as he argued against the impeachment inquiry and went so far as to highlight Trump's efforts to "fix our broken immigration system" and grow the economy.
After the letter, not a single document was produced by the White House, the State Department and other government agencies in response to 71 requests or subpoenas for records, according to the House report on the impeachment inquiry. The administration also sought to block current and former officials from testifying.
Neil Eggleston, who served as White House counsel to Democratic President Barack Obama, said Cipollone's response arguably helped lead to the second article of impeachment, obstruction of Congress. Eggleston said it was a mistake to announce the executive branch was not going to cooperate.
'I AM READY'
Despite his conservatism, Cipollone has friends across the aisle.
Democratic Representative Adam Smith, a former college classmate of Cipollone's and fellow debate team member at Fordham University in New York, has remained friends with Cipollone despite their political differences.
"We try to see past that," said Smith, who recalled that Cipollone had supported Senator Al Gore in his unsuccessful bid for the Democratic presidential nomination in 1988.
When Smith, chair of the House Armed Services Committee, was working on a bill to fund the Pentagon, he said Cipollone put in a good word for him with the White House legislative team.
Smith said he obviously disagreed with Cipollone's approach on the impeachment inquiry, but "we don't talk about that."
Melanie Sloan, a law school classmate who describes herself as being politically progressive, described Cipollone as an "enormously smart, honest, ethical person," and added that she was surprised when he went to work for Trump. She said Cipollone had told her he did not see Trump the way she did. "I can't explain it," she said.
But being White House counsel was the pinnacle of a legal career, she said, and now Cipollone is about to argue a case that will etch him into history.
Scalia, the labor secretary, said he spoke to Cipollone about a week ago. "I said, 'You're getting ready?' And he said, 'I am ready.'"