Donald Trump, Mayor Michael Bloomberg and Pres. Bill Clinton at the Trump National Golf Club in Briarcliff Manor, N.Y., July 2008. (Photo: Sabo Robert/NY Daily News Archive via Getty Images)

Pres. Bill Clinton received information to help him respond to questions about the prospect of Donald Trump mounting a presidential bid all the way back in 1999.

Trump, now the frontrunner in the Republican presidential primary, first flirted with a White House run during the 2000 election cycle, when Democratic presidential primary frontrunner Hillary Clinton was first lady and Bill occupied the Oval Office.

Documents newly released by the William J. Clinton Presidential Library show that the famously loquacious Bill Clinton was prepped to talk Trump while still in the White House. Clinton received a memo about Trump ahead of a White House press conference in a document dated Oct. 14, 1999. Trump, a real estate mogul who has been a tabloid fixture in New York and regularly appeared on television even before launching his own reality show in 2008, was included among other unconventional celebrity candidates.

The guidance for the press conference included a potential question about how “everyone from Warren Beatty to Donald Trump to Cybill Shepherd is contemplating a run for the White House.” White House staff prepared Clinton to respond critically to campaigning by boldface names, and to say that it “trivializes the importance of the office.”

In response to questions about whether the president felt in any way responsible for that trend, Clinton was advised to answer as follows:



“I think it may say something about the way the media covers politics these days, but I have the utmost confidence in the American people to sort out the wheat from the chaff. Regardless of who runs for president or how they’re covered, the public eventually sees through all the smoke and mirrors. And they, after all, have the ultimate power at the ballot box.”

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Clinton was again prepared by staff to take questions about Trump for an interview with Bryant Gumbel on the inaugural episode of CBS’ “The Early Show” in November 1999. In the briefing for that conversation, which was dated Oct. 29, 1999, a question about Trump was included as a follow-up to questions about the Monica Lewinsky sex scandal. Staff advised that Gumbel could ask Clinton about potential campaigns by Trump, Beatty and Shepherd, and whether they were “the result of a demeaning of the office that you’ve contributed to.”

Clinton was advised once again to answer that people would be able to separate the “wheat from the chaff.” He was also prepped to deny his presidency led more celebrities to enter the fray.

“I don’t think what I’ve done has anything to do with such political developments. We go through all sorts of cycles in politics, and we’re in one now, where some people from the entertainment world are talking about running for president,” the answer said. “That’s not a first, by the way. So, it’s a free country, people can chart their own course, and the political process will sort out the wheat from the chaff. I’m not concerned about it.”

The guidance for the “Early Show” interview also suggested that Clinton should encourage people and the press not to focus on the cult of personality in the 2000 election.

“What I am concerned about is whether we’ll get to focusing on the real issues out there — who is best prepared to take this country into the new century, who has the big ideas to meet the big challenges we face, who is equipped to bring about the kind of changes we all need in a rapidly changing country and world,” the suggested answer said. “There’s a natural tendency to cover this campaign on the basis of the various personalities involved, the latest poll numbers, the money game. But I hope we can do better at paying attention to what really matters.”

In addition to these two briefings, the documents released by the Clinton library include other briefing materials that contain press coverage of Trump.

There was also a document confirming that Clinton participated in a photo shoot with Trump at his Manhattan headquarters, Trump Tower, in 2000 and some brief discussion about whether Clinton should send letters to Trump on his 50th birthday and for an occasion at which he was being honored. In both cases, aides said the letters should not be sent. The documents released also included a copy of Trump’s book, “The Art of the Deal,” which he gave to Clinton aide Mark Middleton. Trump signed the book and wrote, “To Mark, Best Wishes … Your Mom Is the Best.”

The Clintons and the Trumps had a variety of contacts before the 2016 campaign. Trump has donated to the Clintons and their charitable foundation. Bill and Hillary Clinton also attended Trump’s wedding in 2005, and their daughters have been friends.

There were reports Clinton called Trump last spring and encouraged him to get involved in politics before the billionaire officially launched his presidential bid. Clinton’s office confirmed a conversation occurred last May, but it denied the election was discussed. Clinton was asked about the call by “Late Show” host Stephen Colbert last October. Colbert alluded to polling that shows Hillary Clinton would easily defeat Trump. Colbert said it would have been “pretty smart” for Clinton to encourage Trump to enter the race. Clinton said the conversation “wasn’t about running for office.”

“His daughter told my daughter that he had tried to call me, and I didn’t get the message. So I simply called him back,” Clinton said. “And I don’t know whether he had ever intended to discuss this with me or not, and this has happened to you before, I bet, I think by the time I got him back, he had forgotten why he called me in the first place, probably.”