A concern of Starr and Kavanaugh in 1997 was whether Clinton would pardon Susan McDougal, who they wanted to be a witness in their investigation of the Whitewater real estate deal.
In one exchange with Clinton's lawyers, for instance, Starr criticized Clinton for alleging "misconduct" on the part of the independent counsel, and in another he accused the President of attempting to dangle a pardon before McDougal.
At the bottom of one document Kavanaugh scrawled: "Totally inappropriate and has practical effect of impeding investigation."
The question of whether a president would pardon someone involved in an investigation is newly relevant, given that President Donald Trump has declined to rule out whether he would issue a pardon for Paul Manafort, his former campaign chairman who was convicted of eight financial crimes last week and faces a second trial in late September.
Kavanaugh, Trump's nominee for the Supreme Court, will face questions next week during his confirmation hearings about whether legal positions he took in the past should apply to Trump. Democrats will push Kavanaugh to explain whether and why some of his legal conclusions have evolved between the time he was investigating one president to the present day when he is the Supreme Court nominee of another.
"The president has the absolute discretion to pardon individuals at any time after commission of the illegal act," Kavanaugh said in 2016 before the Marquette University School of Law.
Trump has declined to rule out a pardon for his former adviser Manafort. A day after he was convicted, the President tweeted that he "felt badly" for Manafort and his "wonderful family."
Starr pointed out that McDougal had criticized his investigation and that Clinton in a PBS interview "appeared to endorse" McDougal's criticisms.
The documents at issue reveal that back in February 1997, Starr contacted then White House lawyer Charles F.C. Ruff to express concern that Clinton, "through his public statements," was reinforcing Susan McDougal's "unlawful intransigence" in refusing to answer questions regarding Starr's Whitewater investigation.
In a follow up letter in the next month, Starr noted that during the same PBS interview Clinton had declined to rule out a pardon for McDougal.
Starr said he recognized that the "Constitution grants the President sole and final authority over pardons" but he argued that the "lingering uncertainty about President Clinton's intentions may be a factor influencing Ms. McDougal's behavior."
McDougal was eventually held in contempt and incarcerated for her refusal to answer questions. Clinton issued her a pardon just before leaving office in January 2001.
In his letter, Starr suggested that the President should "publicly urge Ms. McDougal to testify."
On April 4, Ruff responded. He called Starr's request "unprecedented" and rejected the suggestion that the President had "somehow encouraged Ms. McDougal to violate the law." He said it would be "entirely inappropriate" for the President to "offer advice" to McDougal concerning her legal rights or obligations. He did not mention the pardon issue.
Kavanaugh scrawled on the bottom of Ruff's letter. "Totally inappropriate and has practical effect of impeding the investigation" he wrote.
A person close to Kavanaugh, who reviewed the documents, believes they reflect that Kavanaugh was taking notes on the direction of someone else, likely Starr, and that Kavanaugh had plans to speak to Starr's deputy, Hickman Ewing, about a response to Ruff.
The source said the notes may not have reflected Kavanaugh's personal position on Clinton's conduct. "It would be a stretch," the source said, "to try to attempt to divine Brett Kavanaugh's views on today's issues from notes that may not reflect his views on a case decades ago."
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