WASHINGTON — Before he defended the president, White Counsel Pat Cipollone spent years fighting for Christian expression in Connecticut.

Cipollone was one of the top lawyers representing the Trumbull Knights of Columbus in a 1995 case against the town of Trumbull that was appealed up to the U.S. Supreme Court.

From 1996 to 2001, Cipollone did legal work for the New Haven-based Knights of Columbus, a Catholic fraternal organization and insurance company. He lived in Cheshire.

Since 2001, Cipollone’s legal work has reshaped its focus from religion to business to politics. Now, he is the lead lawyer defending Donald J. Trump, the fourth U.S. president to be impeached. He has spent hours in the U.S. Senate chamber arguing and strategizing in favor of Trump’s acquittal.

“He’s well-known and respected in legal circles,” said U.S. Sen. Richard Blumenthal, D-Conn. “We probably see eye-to-eye on 1/100 of our politics.”

A devoted Catholic, Cipollone, 53, is a founding member of the National Catholic Prayer Breakfast and reportedly participates in the anti-abortion March for Life.

Cipollone grew up in New York and Kentucky, before attending Fordham University and the University of Chicago Law School. He clerked for a judge on the Sixth Circuit Court of Appeals in Kentucky and then worked as a speechwriter for U.S. Attorney General William Barr, when Barr was attorney general in the George Bush administration.

Then, Cipollone joined the law firm Kirkland and Ellis in Washington, D.C. It was working for Kirkland and Ellis that Cipollone joined the Trumbull case.

In the 1980s and 1990s, each year at holiday time, the Trumbull Town Green hosted a decorated Christmas tree and a menorah. In 1993, the Knights of Columbus sought to add a creche to the display.

The town’s first selectman denied the display because the permit application came too late. The next year, the Knights of Columbus tried again. They were awarded a permit, but then 11 days before Christmas, the town revoked the permit noting the creche was religious content.

Two days later, the Knights filed suit with U.S. District Court for the District of Connecticut challenging the town’s decision. Shortly before Christmas, the District Court denied the Knight’s motion.

Cipollone argued before the District Court on behalf of the Knights of Columbus, said Martin Margulies, professor of law emeritus at Quinnipiac University, who represented the town of Trumbull in the case. Margulies met Cipollone in the office of the Trumbull town attorney.

“He struck me as a self-righteous little prig, whose self-imposed mission was forcing his religion on other people,” Margulies said.

One day after the District Court’s denial, the Knights of Columbus appealed to the U.S. Court of Appeals for the Second Circuit, which also promptly denied their case. The Knights of Columbus then brought their case to the U.S. Supreme Court.

In the early 1990s, the Supreme Court was wrestling with several cases regarding religious expression in public spaces. In late June 1995, the Supreme Court ruled that members of the Ku Klux Klan could place an unattended cross on the lawn of the Capitol Square in Columbus, Ohio at Christmas time.

Margulies said lawyers on both sides of the Trumbull case filed amicus briefs in the Ohio case.

The Ohio decision caused the Trumbull case to be remanded to the lower courts, which then supported the Knights’ right to place a creche on the green.

After the Trumbull case concluded, Cipollone took a job with the Knights of Columbus in New Haven as assistant supreme advocate in 1996. In 1998, he was added to the Knights of Columbus Board of Directors (Cipollone no longer holds this position). In 1999, he was made supreme advocate and general counsel of the Knights of Columbus. He left their employ in 2001.

With his wife Rebecca, Cipollone lived in Cheshire from 1997 to 2002, town land records show. The Cipollones have 10 children.

Cipollone then left Connecticut to rejoin Kirkland and Ellis and then take a position with corporate litigators Stein, Mitchell, Beato and Missner in Washington, D.C. Cipollone has been known in D.C. legal circles for years, before he joined the Trump administration.

Blumenthal spoke with Cipollone briefly before the start of the Senate trial on the first day of the Senate impeachment trial on Jan. 21.

“He’s not a social friend, but I’ve run into him professionally,” said Blumenthal.

Blumenthal and Cipollone did not know each other when Cipollone worked and lived in Connecticut, Blumenthal said.

Cipollone advised Trump in an outside role during presidential debates in 2016 and then during Special Counsel Robert Mueller’s investigation. Trump hired him as White House Counsel in December 2018.

Now, Cipollone is heading up of Trump’s legal team that has spent the past two weeks arguing for the president’s acquittal in the Senate. He made headlines last week when House Democrats informed Cipollone they believed he was a “material witness” to the president’s actions toward Ukraine and he should disclose what events he has first-hand knowledge of to reveal any conflicts of interest in his arguments. The White House shrugged off this challenge and Cipollone has continued his work on the case without such disclosures.

But on Friday, Cipollone role in the Ukraine campaign gained new attention after more of the manuscript of former National Security Adviser John R. Bolton’s book was leaked. The New York Times reported Bolton’s book says Cipollone participated in a May meeting in which Trump told Bolton to ensure Ukraine would meet with his personal lawyer Rudy Giuliani to discuss the investigations Trump wanted.

House impeachment managers discussed this development in their closing arguments Friday, advocating in favor of Bolton’s testimony to the Senate.

Cipollone has had fewer minutes at the Senate podium than some other lawyers on the president’s team, like his deputy Patrick Philbin. But Cipollone took the star spot when concluding the White House’s opening arguments Tuesday. He urged Senators to quickly end the trial.

“You know what the right answer is in your heart,” Cipollone said. “You know what the right answer is for your country. You know what the right answer is for the American people.”