Mr. Cipollone served a clerkship with Judge Danny Julian Boggs, a Reagan appointee, on the Sixth Circuit Court of Appeals.
As part of the interview process, Mr. Cipollone took the judge’s famously difficult “general knowledge” quiz, which he used to gauge knowledge beyond the law. In Mr. Cipollone’s year, potential clerks had to answer 64 questions, including, “What was the Trail of Tears?” “What did the battles of Actius, Lepanto and Salamis have in common?” and “When and what was the Edict of Nantes?” (Judge Boggs said he had looked back in his files and could not find Mr. Cipollone’s score.)
Judge Boggs recently had lunch with Mr. Cipollone in the White House mess. “I complimented him on not seeing his name in the paper,” the judge said, “which means he’s doing a good job.”
Mr. Cipollone went from Judge Boggs’s chambers in Louisville to Washington, and a speechwriting job with William P. Barr, who was attorney general in the George Bush administration and was named attorney general by Mr. Trump a few months after Mr. Cipollone arrived at the White House.
A fellow clerk, Jennifer Hall, recalled sitting in Judge Boggs’s bookshelf-lined chambers between Mr. Cipollone and another clerk, Stephen Vaughn, now a trade lawyer in Washington. “They would yell at each other over me,” she recalled, “listening to Rush Limbaugh.”
Mr. Cipollone and his wife, Rebecca Cipollone, have 10 children. The youngest is a 10-year-old son and the oldest a 26-year-old daughter, who works at Fox News for Laura Ingraham, the conservative commentator, who was introduced to Catholicism by Mr. Cipollone.
Mr. Cipollone is a founder of the National Prayer Breakfast, participates in the anti-abortion March for Life, and events that draw Washington’s Catholic elite, like the Red Mass, celebrated each year at St. Matthew’s Cathedral on the Sunday before the Supreme Court session begins. (Mr. Cipollone was absent when the event was held this past weekend.)