When White House counsel Pat Cipollone argues President Donald Trump's case in a Senate trial this week, he will also be defending his role in a controversial legal strategy that helped lead to Trump's impeachment on a charge of obstructing Congress.
Democratic lawmakers in the House of Representatives said on Tuesday that evidence heard in their impeachment inquiry indicates he "played an instrumental role" in that obstruction and his representation of Trump threatens to undermine the integrity of the trial.
They have charged Trump with abuse of power for allegedly pressuring Ukraine to investigate a political rival, former Vice President Joe Biden, and obstruction of Congress for undertaking "an unprecedented campaign" to prevent them from probing those allegations.
In a letter sent to Cipollone just hours before the trial was set to begin in earnest, the lawmakers urged the White House counsel to disclose the full extent of his knowledge of Trump's alleged pressure campaign and said evidence suggested his office had been directly involved "in potential efforts to conceal President Trump's scheme from Congress and the public."
There was no immediate comment from the White House.
One of the main pieces of evidence to support the obstruction charge against Trump 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 Democratic-led House of Representatives, bringing him public attention that friends and colleagues say he has long eschewed, unlike many of Trump's lawyers.
The arguments and political tone in his 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, defended him, saying the arguments in Cipollone's letter were "exactly what the founders had in mind in crafting a constitution that respects separation of powers."
Now Cipollone will be in a much brighter spotlight in a televised trial that will take him from his second-floor White House office - where he has a photograph of his family, including his 10 children, with Trump - to the Senate chamber, where he will help lead the Republican president's defense.
The trial begins in earnest in the Senate on Tuesday.
Democrats have called for Trump's removal from office, describing him as a danger to American democracy and national security. Trump and his lawyers say he has done nothing wrong and that Democrats are simply trying to stop him from being re-elected. Trump is expected to be acquitted in the trial in the Republican-controlled chamber.
While Trump was at his Mar-a-Lago resort in Florida for the Christmas holidays, Cipollone was in his office 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.
"He is a rare combination of law review smart and street smart," said Scalia, who was editor-in-chief of the school's legal journal when Cipollone was on staff.
Though plain-spoken, Cipollone is expected to avoid Trump-like rhetorical bombs when he argues that there were no grounds for House Democrats to charge Trump with abuse of power or obstructing Congress. The 53-year-old Republican will likely say that Trump was exercising his right to protect confidential communications. His argument will follow those of the House managers who are presenting the case against Trump.
Cipollone, who became White House counsel in December 2018, was first 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, a 6-foot-3-inch bespectacled man, 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 show loyalty to Trump as he argued against the impeachment inquiry and highlighted 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's 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's legislative team.
Smith said he obviously disagrees 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, said Cipollone was 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.'"