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Editor's note: Parts of this story contain content that is sexually explicit.
Twenty years ago Friday, the long-running independent counsel Whitewater investigation had reached a crossroads, far from where it started, with prosecutors questioning President Bill Clinton about his relationship with a former White House intern, Monica Lewinsky.
That night, Clinton addressed the nation. "I answered their questions truthfully, including questions about my private life," Clinton said. "Questions no American citizen would ever want to answer."
One of the people involved in drafting those questions, Brett Kavanaugh, is now President Trump's nominee for the Supreme Court.
In 1994, Kavanaugh wasn't even 30 years old. He was finishing up a Supreme Court clerkship and was recruited to a big deal law firm, when the guy who recruited him, Ken Starr, was drafted to take over the independent counsel investigation into Whitewater.
"So, I immediately sat down with Brett over lunch and encouraged him to postpone the private practice of law by say, oh, six months or so, and come join my team in the Washington, D.C., office," Starr told NPR.
Starr chuckles slightly as he talks about the timeline. What was supposed to be six months turned into nearly four years and what started with an investigation into a bad land deal veered ultimately into the president's sex life and the steps Clinton took to cover up an affair. This brought significant criticism to the Office of Independent Counsel and its investigation, particularly from those on the left, that continues to this day.
Kavanaugh was part of what Starr and others in the office called "the brain trust," the lawyers who puzzled through the many legal and constitutional questions that came up over the course of the investigation.
How close was Kavanaugh to Starr and the investigation? Kavanaugh can be clearly seen over Starr's left shoulder in C-SPAN's recording of Starr testifying before Congress in 1998, as the House considered impeachment against the president.
Kavanaugh also argued in favor of investigating the suicide of Vince Foster, the White House deputy counsel, even though two prior investigations had already concluded that his death was a suicide.
"We are currently investigating Vincent Foster's death to determine, among other things, whether he was murdered in violation of federal criminal law," Kavanaugh wrote, according to a memo obtained by The Washington Post. "[I]t necessarily follows that we must have the authority to fully investigate Foster's death."
Kavanaugh concluded that the death was, in fact, a suicide. But during his investigation, he even argued — in his only turn before the Supreme Court -- that notes Foster's lawyer made were no longer covered by attorney-client privilege because Foster was dead. The court disagreed by a 6-3 margin.
When it got to the point of questioning Clinton in August 1998, Kavanaugh and others in the Office of Independent Counsel felt it was necessary to ask questions that were intimate in nature.
"We had to get to the bottom of the facts," Starr said. "The facts were unpleasant, but it was our duty to as best we could to get the facts that bore on these serious issues of perjury, intimidation of witnesses and obstruction of justice."
On the eve of the interview with Clinton, Kavanaugh sent a memo to Starr and the other lawyers in the office arguing that Clinton had "disgraced his office, the legal system, and the American people by having sex with a 22-year-old intern and turning her life into a shambles — callous and disgusting behavior that has somehow gotten lost in the shuffle."
According to the book The Death of American Virtue: Clinton vs. Starr, Kavanaugh also proposed 10 sample questions about the president's relationship with Lewinsky, with descriptions of sexual acts, that we should warn are, both detailed and explicit:
"If Monica Lewinsky says that you ejaculated into her mouth on two occasions in the Oval Office area, would she be lying?
"If Monica Lewinsky says that on several occasions you had her give [you] oral sex, made her stop, and then ejaculated into the sink in the bathroom off the Oval office, would she be lying?
"If Monica Lewinsky says that you masturbated into a trashcan in your secretary's office, would she [be] lying?"
In the end, the questions asked were not nearly as graphic as what Kavanaugh proposed, but his sentiment about the direction of the questioning was shared by at least some of his colleagues.
"There's no point in pussyfooting about it," said Sol Wisenberg, one of three career prosecutors who conducted the questioning.
Clinton had testified under oath in a civil deposition about his relationship with Lewinsky, and the independent counsel team had detailed information from Lewinsky and others that contradicted his testimony.
"[In the civil deposition], he was asked about sexual relations with Monica Lewinsky," Wisenberg said, "asked whether he was alone with her, denied that he was, then we have all this information to the contrary from Monica Lewinsky, and, so, it becomes very important to try to corroborate."
But in the midst of all this, Kavanaugh had very serious doubts about whether an independent counsel — as the law was structured at the time — was the best way to investigate a president. In February 1998, during a brief stint back in private practice, Kavanaugh was part of a panel discussion at Georgetown University.
He raised the question of whether a sitting president could be subject to criminal indictment at all, a "lurking constitutional issue ... which at some point here should be resolved so that we can determine whether the Congress or an independent counsel can investigate a president when his conduct is at issue."
This prompted the moderator to ask for a show of hands. Who thinks that a sitting president can't be indicted while in office? Kavanaugh raised his hand.
"I tend to think it has to be the Congress, because of the kind of attacks that we've seen recently," Kavanaugh said referencing the intense criticism Clinton allies hailed on the investigation. "It is war, and if it's going to be be war, it's got to be Congress and not an isolated prosecutor appointed by a panel of three judges we've never heard of."
Kavanaugh returned to the trenches in the independent counsel's office, and, ultimately, wrote key portions of Starr's report to Congress. Starr said Kavanaugh wrote the section of the report making the legal case for impeachment, but not — Starr was quick to point out — "the narrative section or the fact section of the report."
As Starr campaigns for Kavanaugh's confirmation, he made that point because the narrative section became a flashpoint in the political fight over the investigation because it was so sexually explicit. Even though Kavanaugh pushed to ask those explicit questions, when it came time to send the report to Congress, he urged caution.
In a memo attached to a draft he asks in all caps and bold, "IS IT TOO GRAPHIC?" followed by "SHOULD IT BE MORE GRAPHIC (kidding)?"
The Office of Independent Counsel delivered to the House 36 sealed boxes containing two full copies of its referral — and a warning, in a cover letter that Kavanaugh helped write, which said, in part, "Many of the supporting materials contain information of a personal nature that I urge the House to respectfully treat as confidential."
It turns out there was good reason for caution. The House, led by Speaker Newt Gingrich, didn't heed the warning and released the documents in full on the Internet. Kavanaugh's position, voiced by many on the team including Starr, was that it wasn't their fault for including the details, it was the House's fault for releasing them.
"We regretted, not the report, I certainly did not regret the report," Starr said, "we did our duty as we saw it, but we did very much regret and ... we were genuinely surprised by the fact that the House of Representatives would see fit simply to release the material without having read, reviewed and redacted."
Kavanaugh suggested that very argument in a memo dated Feb. 5, 1999. He complained that the office had a "self-defeating pattern of failing to put the best face — which happens to be the truth — on the referral's inclusion of detail."
He added, "This is important for Ken's reputation, for that of the Office, and for all of us individually."
A Gallup poll from November 1998 found Clinton was far more popular than Starr, and public opinion of the investigation was dismal.
In December 1998, Kavanaugh sent a memo to Starr, titled, "Overall Plan." The House had already impeached Clinton. The Senate would ultimately vote to acquit him, but that hadn't happened yet:
"After the Senate has concluded, I would send a letter to the Attorney General explaining that we believe an indictment should not be pursued while the President is in Office (and that we also do not believe that we should keep our Office open while we wait). Rather, I would explain that we believe that the next President (and Attorney General) should make the decision whether to indict Mr. Clinton. Therefore, I would refer the Clinton perjury/obstruction case to the Attorney General for her to hold in abeyance until the President leaves office and the next President can decide what to do. I also would publicly announce our letter at the time it is sent.
Kavanaugh remained loyal and proud. In late 1999, he spoke at a dinner honoring Starr that was televised by C-SPAN.
"And maybe I'm an optimist. But one day, I for myself hope to be able to call him 'Mr. Justice Starr,' " Kavanaugh said to a little laughter and a lot of applause. "And we all know that might not ever come to pass, but if it does not, shame on the country."
Starr was far too controversial a figure for that to ever happen, but Starr is now hoping the young lawyer he worked with so closely in the 1990s will instead become the next Supreme Court justice.
One reason Kavanaugh may have gotten the nod from Trump, a president who himself is wrapped up in a special counsel investigation, is a law review article Kavanaugh wrote a decade ago.
In it, he argued that a president shouldn't be subject to civil litigation or criminal investigation while in office because the demands of the office are too great.
"This is not something I necessarily thought in the 1980s or 1990s," Kavanaugh wrote in the 2009 Minnesota Law Review article. "Like many Americans at that time, I believed that the President should be required to shoulder the same obligations that we all carry. But in retrospect, that seems a mistake. Looking back to the late 1990s, for example, the nation certainly would have been better off if President Clinton could have focused on Osama bin Laden without being distracted by the Paula Jones sexual harassment case and its criminal investigation offshoots."
The remedy, he argued, for if a president does something "dastardly" would be impeachment.
"No single prosecutor, judge, or jury should be able to accomplish what the Constitution assigns to the Congress," he wrote.
It's an extension of a legal view he held even when he was a key player in the highly controversial criminal investigation of a president who committed perjury while a defendant in a civil lawsuit.
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