Aides to Clinton prepped the then-president on how to answer questions about a possible Trump presidential run nearly 17 years ago.
In October 1999 -- the same month
that Trump announced on CNN that he had formed a presidential exploratory committee to consider running under the Reform Party ticket -- White House aides gamed out potential questions about whether Clinton's scandals contributed to the rise of Trump and other celebrities pondering the presidency.
"Is this the result of a demeaning of the office that you've contributed to?" read a potential question included in the President's briefing book before an October 31 interview with CBS News.
Clinton's briefing book for a news conference that same month also floated a potential question about whether Clinton was "responsible for that trend" of figures like Trump and actor Warren Beatty considering presidential runs.
"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," read the suggested response Clinton's aides prepared.
The Clinton Presidential Library released the documents as part of a Freedom of Information Act request, and comes at a time when Trump is the front-running Republican presidential candidate and could face off against Clinton's wife, who is leading in the Democratic primary race.
The documents also shed light on the longstanding relationship between Trump and the Clintons.
A canceled birthday letter
Clinton's personal secretary, Betty Currie, on June 10, 1999, penned an email to Karen Hancox, the deputy director of political affairs at the time, asking for her thoughts on "sending a birthday letter to Donald Trump -- who turns 50 on June 14."
Three days letter, Currie emailed again to say simply, "Cancel letter to Donald Trump." It's unclear why the letter was canceled.
The documents released also included an autographed copy of "The Art of the Deal" that Trump sent to Clinton White House aide Mark Middleton.
White House kept tabs on Trump
The documents also show that White House aides were keeping tabs on news about the billionaire in 1999 and 2000 as he was exploring a presidential run.
White House aides sent around notifications and guidance on Trump's appearances on TV news shows at least twice. And a White House aide also flagged a potential controversy involving Trump's relationship with the rapper and hip-hop mogul Sean Combs, who had just been hit with a gun charge at the time.
The relationship between Trump and the former president wasn't limited to the 1990s, though. Trump would invite the Clintons to his 2005 wedding.
'One of the great abusers'
But today, Trump is singing a different tune about the former president as he prepares for a potential general election campaign against Hillary Clinton.
Trump in January
referred to the former president as "one of the great women abusers of all time" and accused Hillary Clinton of being an "enabler," referring to the 42nd president's sex scandals -- despite Trump defending the former president at the time of the Monica Lewinsky scandal.
Trump has since argued that he fostered a positive relationship with the Clintons to help his business interests.
"As a businessman I got along with everybody," Trump said in January on CNN's "New Day." "It was important for me to get along with them."