Kavanaugh wrote a sexually graphic memo while sleep-deprived during the Starr probe, a report said.
A former colleague of Kavanaugh's told The Atlantic that the judge later "regretted" its tone.
The memo had a list of explicit questions for former President Bill Clinton about Monica Lewinsky.
Justice Brett Kavanaugh wrote a memo with a list of sexually explicit questions for former President Bill Clinton during "a fog of sleep deprivation" and later regretted how it came across, a former colleague of Kavanaugh's told The Atlantic.
After a series of clerkships, Kavanaugh cut his teeth in the conservative legal world on special prosecutor Ken Starr's investigation into the Clintons. The wide-ranging probe scrutinized the Clintons' business dealings in Arkansas and Clinton's lies about his relationship with former intern Monica Lewinsky, which eventually led to his impeachment.
The memo, dated August 15, 1998, resurfaced during Kavanaugh's 2018 confirmation hearings. It was titled "Slack for the president?"
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In it, Kavanaugh expressed outrage about Clinton's behavior in office, writing, "The president has disgraced his office, the legal system, and the American people by having sex with a 22-year-old intern and turning her life into shambles." He called Clinton's actions "callous and disgusting behavior."
The memo included a suggested list of sexually graphic questions for Clinton, such as "If Monica Lewinsky said you inserted a cigar into her vagina, while you were in the Oval Office area, would she be lying?" and "If Monica Lewinsky says that you had phone sex with her on approximately 15 occasions, would she be lying?"
The former coworker, Robert Bittman, told The Atlantic's McKay Coppins for a profile of the justice published on Thursday that Kavanaugh later "expressed regret" for the memo's tone. Bittman also told McKay the memo was written while Kavanaugh was sleep-deprived.
Kavanaugh's work on the hard-charging investigation cemented his status as a respected conservative lawyer and a team player.
Colleen Covell, a woman who went on a date with Kavanaugh while he was working on the Starr probe, told The Atlantic that at the date, Kavanaugh got drunk and began ranting about the Clintons, saying, "They're total crooks!" and "I can't believe you voted for them!"
Kavanaugh's work on the Starr investigation landed him a stint in the White House counsel's office and then 12 years on the District of Columbia Circuit Court of Appeals.
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