Papers from the Clinton White House released Friday detail much of the behind-the-scenes legal work of the White House as President Bill Clinton dealt with multiple scandals and controversies in his second term.

In one memo, Elena Kagan, in her days as a White House lawyer before she was nominated to the Supreme Court, even drops the F-bomb.

The documents, which had been secret until their release through the William J. Clinton Presidential Library, also detail the White House’s reaction to the Oklahoma City bombing and concerns about litigation stemming from Clinton’s doomed proposal to extend universal health care to Americans. They come as speculation swirls that Hillary Clinton will seek the Democratic presidential nomination in 2016.

The documents were withheld from publication until 12 years after the end of the Clinton administration, under the Presidential Records Act.

Here are the highlights from the 9,800 pages released Friday by The National Archives and Records Administration:

Future Justice Uses Expletive

In a memo about the Paula Jones lawsuit, Kagan describes a media show mix-up, uses a curse word and says she feels like an idiot. In the high-stakes case, the president denied Jones’ allegation that, while he was governor and she was a state employee in 1991, he exposed himself and sought oral sex from her in a Little Rock hotel room.

Kagan wrote to White House Counsel Jack Quinn in May 1996 to describe some confusion over the media. Kagan spoke to a television show host, while someone else at the White House was speaking to the show’s producer and trying to convince him not to do a segment.

“I realize now that I may have really fucked up in not mentioning to you that she spoke to me this morning to find out what the situation was,” Kagan wrote. “God, do I feel like an idiot.”

High Stakes and Tiny Details

Dozens of edits to draft court filings and memos illustrate the kind of details the lawyers fretted over as Clinton challenged having to testify in the Jones case.

The Supreme Court would eventually rule unanimously that the Constitution does not shield sitting presidents from having to defend themselves against lawsuits over acts unrelated to their official duties.

Kagan sent a May 13, 1996, memo to Bruce Lindsey, assistant to the president and senior adviser, about simply removing a cover page from the litigation.

“I just noticed that Bob and Amy have removed from the cover page the names of the Arkansas-based attorneys,” Kagan wrote. “Bob and Amy think that it looks unseemly for the president to have so many lawyers working on this case. (I tend to agree.)”

Handwritten notes on the side of one draft of a draft Supreme Court brief state: “In general, can we use a president instead of the president as much as possible.”

Kagan, in another memo, suggests ending a brief to the Supreme Court with the idea that a ruling against Clinton will lead to many more lawsuits against presidents, often for political reasons.

“The future implications of the holding here are very important for the court to consider,” Kagan wrote. “Of course the ‘floodgates’ argument is speculative in some sense, but given the litigiousness of our society and the gutter level of our politics—both of which we think the brief should feel free to mention—it strikes most people as true, especially if phrased in a non-hysterical manner.

“And it gets the Court thinking about the potentially quite awesome ramifications of this suit. (In the end, most of these nine Justices are not going to want to be responsible for throwing a new and disgusting element into American political life.)”

Health Care Legal Woes

The Clintons were anticipating legal challenges as they crafted their plan to overhaul the health care system, foreshadowing the lawsuits that President Barack Obama’s signature health law (PL 111-148, PL 111-152) has faced since its enactment in 2010.

“It is possible that some confusion concerning the constitutional legitimacy of the Health Security Act will arise precisely because it is so comprehensive and detailed, and thus necessarily will affect all the major components of our current health care delivery system,” Walter Dellinger and H. Jefferson Powell wrote in an Oct. 29, 1993, memorandum to Attorney General Janet Reno and Associate Attorney General Webster Hubbell.

“There may indeed be no historical analogue of a single bill that does so many things at once.”

In a separate memo for the Health Care Task Force a month earlier, the Office of Legal Counsel outlined a number of legal concerns that could be prompted by the overhaul. Among the “Substantive Constitutional Issues” listed in the document is an entry on “required participation in national health care.”

“Like the New Deal, some aspects of health care reform are likely to be assailed in Congress and (if enacted) in the courts as unconstitutional,” wrote Dellinger, acting assistant attorney general. “Careful and creative legal advice in the formulation of the President’s proposals will be critical to his initiative’s success in Congress and to the ability of the Department of Justice to defend health care reform in any lawsuits that ensue.”

Still, Dellinger said his office’s preliminary assessment was that the challenges “should clearly fail under current standards.”

Supreme Court Nomination Speech That Never Was

In 1994, Clinton considered federal Appeals Judge Richard Arnold for the U.S. Supreme Court to replace retiring Justice Harry Blackmun.

The documents released Friday include the speech prepared for Clinton to announce Arnold’s nomination to the Supreme Court — as well as a letter saying he ultimately decided not to pick Arnold because of Arnold’s health issues. Arnold died in 2004.

“As you know, I share your support for Judge Arnold and regret that the President did not feel he could name Richard at this time,” Lindsey wrote in a May 17, 1994 letter. “Hopefully, the health issues will be resolved, and I expect the president to seriously consider Judge Arnold for future vacancies.”

Clinton’s speech shows just how close he was to nominating Arnold, and how heartbreaking it was for him to ultimately have to pass him over.

“Judge Arnold, without dispute, is one of the outstanding jurists of our age,” the speech reads. “He has a tight fisted grasp of the law, a boundless respect for the constitutional and legal rights of the American people, and a large spirit that is the foundation for his searching and restless intellect.”

“When Judge Arnold writes opinions, his pen speaks with a spare and elegant clarity.”

Clinton eventually picked Stephen G. Breyer as the nominee to the high court.

Don’t Ask, Don’t Tell

Years after the armed forces scrapped Don’t Ask, Don’t Tell, the documents released  Friday show just how much the administration struggled with it.

Hundreds of pages of legal memos propose a range of approaches to the issue of gay and lesbian soldiers and attempt to anticipate legal challenges. The documents question whether a public kiss might convey “homosexual conduct” (described as “carnal acts,” which most courts at the time said the military could ban) or “homosexual orientation” (which courts were far more divided about the military forbidding).

But prohibiting homosexual acts without running into equal protection violations was something of a minefield. One note from Clifford Sloan, then associate counsel to the president, advised deleting ‘handholding and kissing” as examples of prohibited conduct in a policy memo.

“It seems unnecessary, and it may appear to demean the tone of the policy,” he wrote. “It may also raise needless controversies about the circumstances in which handholding, for example, could be seen as far from an acknowledgement of homosexuality (e.g., clasping hands after a high-five).”

One lengthy hand-written set of notes from a meeting of presidential advisers identified one possible solution: “We stop asking.”

Gun Control

A February 2000 memo mapping out priorities for the waning months of Clinton’s term warned the president that getting gun control legislation through Congress would be an uphill fight, a lesson the current occupant of 1600 Pennsylvania Ave. learned first hand more than a decade later.   The memo to Clinton — from his deputy chief of staff Karen Tramontano and senior adviser Thomas Freedman — said, “Successfully concluding the gun issue is less likely this year given the nature of the political debate and the current make-up of Congress.” Tramontano and Freedman continued that “most political pundits are predicting that nothing will get done” on gun control.   But they went on to suggest Clinton could still “engage the debate” by marking anniversaries of various school shootings.

Regulating Militia Groups

The 1995 Oklahoma City federal building bombing resulted in the Clinton administration adopting several policies that helped form the backbone of modern U.S. counterterrorism, but it dropped one radical notion — attempting to have the federal government regulate militia groups.

Bomber Timothy McVeigh had ties to militia groups, and that clearly weighed heavily on the administration. At the request of the White House Office of Legal Counsel, Justice Department lawyers worked up a memo on possible regulation of paramilitary activities a month after the bombing.

The memo said that there was no constitutional bar to requiring paramilitary groups to register with the government and disclose the names of their officers, although it also cautioned that its research was so preliminary that it shouldn’t be used as the basis for action. Other documents released show that the administration was inquiring into whether Congress could regulate militias under the Second Amendment or its powers over interstate commerce, and if the government could require such groups to provide lists of their memberships and weapons caches. Such questions came from the offices of then-Chief of Staff Leon Panetta and his deputy, Harold Ickes.

They were later quashed, however. A memo from the White House counsel’s office produced the same day as the Justice Department preliminary analysis said that “all of the lawyers analyzing these proposals (in this office and at DOJ) strongly believe it is a serious mistake — as a policy but especially as a political matter — to impose militia controls of the type now being discussed, even if they were constitutional.”

There were 41 states with militia bans in place, the memo notes, and groups from the ACLU to the NRA were advising against an overreaction to the bombing.

Spying on Citizens

At a time when the country is in the midst of a gut-check on how much information government agencies can collect on citizens, the documents provide a glimpse at the origins of those surveillance policies.

A slew of background briefings from the White House, Justice Department and FBI written after the Oklahoma City bombing called for Clinton and Congress to give federal agencies easier access to credit reports, digital telephone records and call logs. Those authorities were labeled as essential in preventing another terrorist attack.

The administration sought authority “to conduct limited electronic surveillance to collect intelligence on individuals or groups suspected of advocating or planning terrorist attacks,” says one Justice Department draft memo.

Many of the memos call for a lessened standard of evidence for agencies to obtain permission to use pen register and trap-and-trace devices – electronics that could record calls made and received from a telephone line – from the intelligence courts created by the Foreign Intelligence Surveillance Act (PL 95-511).

That proposal made it into a Clinton-backed bill in 1995 — introduced by then-Sen. Joseph R. Biden Jr. — and years later, after another major terrorism attack, the 2001 Patriot Act (PL 107-56) adopted similar language.