With Republican Senate Judiciary Committee Chairman Charles Grassley having scheduled the Supreme Court confirmation hearing for Judge Brett Kavanaugh to begin just after Labor Day, government officials have been working hard to release as much of the voluminous record of his past work as possible. Monday’s document dump included a lurid 1998 memorandum that Kavanaugh wrote as a lawyer working for Independent Counsel Kenneth Starr’s investigation of President Bill Clinton. In it, Kavanaugh proposed ten questions for prosecutors to ask Clinton when he appeared before a grand jury two days later.

Among the questions Kavanaugh proposed were:

“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 b[e] lying?”

Readers who are too young to recall or have mercifully forgotten the details of the Lewinsky Affair may find those questions shocking. They would understandably and rightly condemn Bill Clinton for having had an extramarital affair and for having used the power of his office to seduce a 22-year-old intern.

Yet looking back at that twenty-year-old memo, we can also wonder why the Independent Counsel—originally appointed to investigate an Arkansas investment deal—was interested in the precise details of where the president ejaculated. After all, Clinton was not a defendant in a rape case, whose testimony might be compared with physical evidence. There has never been any allegation that Clinton coerced Lewinsky into having a sexual relationship with him.

To evaluate whether Kavanaugh had good reason to propose his remarkably explicit questions, we need to revisit the Starr investigation.

From Whitewater to Sexual Harassment to Consensual Sex

In 1994, under a since-expired law, a court appointed Kenneth Starr, a former federal judge and Solicitor General for President George H.W. Bush, as Independent Counsel and tasked him with investigating allegations that in the 1970s and 1980s, Bill and Hillary Clinton had committed illegal acts in connection with a failed business venture known as the Whitewater Development Corporation. Although others were convicted, the Clintons were never charged with any crimes arising out of Whitewater.

However, before his commission expired, Starr’s portfolio expanded. A confidante of Lewinsky, Linda Tripp, had told Starr that conversations between Lewinsky and Clinton indicated that Lewinsky and Clinton would perjure themselves when asked about the Lewinsky affair in an unrelated case, a lawsuit by Paula Jones, who claimed that Clinton had sexually harassed her when he was Governor of Arkansas. Armed with an expanded mandate by Clinton’s Attorney General, Janet Reno, Starr and his minions zeroed in on the Lewinsky affair.

Whether Clinton had consensual extramarital affairs was not obviously relevant to the Jones case. After all, while infidelity involves a serious betrayal of a spouse, it does not by itself involve any kind of coercion. At most, the Lewinsky evidence was modestly relevant in the Jones case: proof that Clinton had an affair with an intern has some bearing on whether Clinton is the sort of person who uses the power of his office for sexual gratification.

If the Jones case arose today, questions like those proposed in Kavanaugh’s 1998 memo would be clearly disallowed under Federal Rule of Civil Procedure 26(b), which limits discovery (including depositions) to matters that are both relevant to a claim or defense and “proportional to the needs of the case.” To be sure, that language reflects restrictions that were adopted in 2000, but even under the version of the rule in effect in 1998, discovery was not supposed to be used for purposes of harassing a party or witness. If the trial judge in the Jones case had applied that standard correctly, she would not have allowed Jones’s lawyers to question Clinton about the precise details of his affair with Lewinsky.

Nevertheless, allow it she did, and the fact that the questions should have been ruled inadmissible was no justification for Clinton’s lying—by denying the affair with Lewinsky—in the Jones case. It was to prove that Clinton lied about Lewinsky in his Jones deposition that Kavanaugh proposed the X-rated line of questioning.

Or at least that’s what Kavanaugh wrote in his memo.

The Meaning of “Sexual Relations”

After Clinton testified before a grand jury, Starr’s team—including Kavanaugh—wrote a “referral” to Congress outlining the crimes they believed that Clinton had committed so that the House of Representatives could decide whether to impeach him. The “Starr Report,” as it came to be known, is part softcore porn, part legal brief. For present purposes, its crucial passages describe how, in his grand jury testimony, Clinton maintained that he was telling the truth in his Jones deposition when he denied having a “sexual relationship” or engaging in “sexual relations” with Lewinsky, even though they had engaged in various sexual acts.

Clinton explained to the grand jury that the term “sexual relationship” was not given any special definition for the Jones deposition and that the ordinary person would understand it to mean sexual intercourse, in which he and Lewinsky had not engaged. He also claimed that his denial of “sexual relations” was truthful because the judge in the Jones case had given that term a special definition. Under Clinton’s rather legalistic understanding of that definition, A has sexual relations with B if A has contact with B’s “genitalia, anus, groin, breast, inner thigh, or buttocks,” but not if only B has contact with those body parts of A. And because the sexual acts were one-sided according to Clinton—with Lewinsky pleasuring him but not vice-versa—he (A) did not have sexual relations with Lewinsky (B).

Clinton’s understanding of the Jones case definition of sexual relations was highly formalistic. It had the odd implication that Lewinsky, by performing oral sex on Clinton, had sexual relations with Clinton but that he did not thereby have sexual relations with her.

Still, the law is full of specialized definitions that do not conform to everyday usage. After all, under precedents that Judge Kavanaugh heartily endorses, corporations are people, and the expenditure of large sums of money on elections is speech. So the idiosyncratic nature of Clinton’s view of the Jones definition should not overly concern us.

The Starr report makes much of the fact that Lewinsky’s grand jury testimony contradicted Clinton’s denials that he had ever pleasured her. It is persuasive on this point: Clinton was almost certainly lying in his Jones deposition and again in his grand jury testimony. But note, crucially, that given the eventual write-up in the Starr Report, fully half of Kavanaugh’s proposed lurid questions were completely unnecessary, because they asked about the specifics of sex acts done for Clinton’s gratification, not Lewinsky’s. Even if Clinton had admitted that Lewinsky had performed oral sex on him, that would not have contradicted his contention that he never had “sexual relations” with her.

To be fair to Kavanaugh, when he wrote the memorandum, he was aware of the definition of “sexual relations” that had been used in the Jones case but may have been unaware of the special sense in which Clinton would claim to have understood it two days later in his grand jury testimony. Even so, however, there is simply no legal justification for the sexual detail in Kavanaugh’s proposed questions. If he wanted to establish that Clinton was lying in the Jones case and bait him into lying again before the grand jury, two questions would have sufficed: (1) Did you ever have contact with the genitalia, anus, groin, breast, inner thigh, or buttocks of Lewinsky? And (2) Did she ever have contact with your genitalia, anus, groin, inner thigh, or buttocks?

Such questions would have been extremely awkward at best, but they would not have, to borrow a term from Kavanaugh’s own memo, “disgraced . . . the legal system.” Taken as a whole, it is apparent that Kavanaugh wanted Clinton humiliated as punishment for what Kavanaugh regarded as “abhorrent” behavior.

Judge Kavanaugh’s Current View

Does the twenty-year-old memo from attorney Kavanaugh bear on whether Judge Kavanaugh should be confirmed to the Supreme Court? Arguably not. In a 2009 article in the Minnesota Law Review, Judge Kavanaugh wrote that his experience as staff secretary for President George W. Bush had led him to appreciate the demands on a president’s time in a way that he had not previously. He explained that “in retrospect . . . 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.”

Yet in the very same paragraph in which that language appears, Judge Kavanaugh also wrote that all of the key legal actors—including Ken Starr—acted in accordance with “their proper duty under the law as it then existed.” He then proposed that Congress should grant the president temporary immunity from civil and criminal proceedings.

Notably, Congress has not done that. Although the law under which Starr operated as Independent Counsel expired, executive branch regulations allow for the appointment of a special counsel, such as Robert Mueller. Meanwhile, Congress has not granted the president temporary or other immunity. Thus, the relevant “law as it then existed” during the Starr investigation is also the law that exists today. Accordingly, by the logic of his own article, the views lawyer Kavanaugh expressed in 1998 remain relevant to the views of Judge Kavanaugh in 2018.

With that in mind, and inspired by attorney Kavanaugh’s proposal of questions, I conclude with a proposed question for one of the senators to ask of him:

In your 8/15/98 memorandum to Judge Starr, you said that President Clinton brought his troubles upon himself. You repeated that statement virtually verbatim on page 1460 of your 2009 Minnesota Law Review article. In your 1998 memo you concluded your enumeration of Clinton’s misdeeds this way: “He has lied to the American people. He has tried to disgrace you” (meaning the Independent Counsel) “and this Office with a sustained propaganda campaign that would make Nixon blush.” That is why you found “the idea of going easy on” President Clinton “abhorrent.” Judge Kavanaugh, my question is this: Do you still regard it as abhorrent to go easy on a president who has lied to the American people and conducted a sustained propaganda campaign against a special prosecutor and his office?