Top Takeaways From the Clinton Library's Document Dump

— -- The Clinton Presidential Library released half of its documents pertaining to Donald Trump and the Trump Organization today and the documents shed light on the fraught relationship between the real estate mogul and Clintons.

More than 200 of 464 pages have been uploaded to the library's website following a Freedom of Information Act (FOIA) request. One of the pages is a signed copy of Trump's book "Art of the Deal" for a Clinton aide.

Here are some of the highlights between the business mogul and the former president:

Press Conference and Interview Prep

In briefing materials written up for President Clinton on domestic policy issues for a press conference, aides included an answer for an anticipated question on Trump’s candidacy for president in 1999.

The briefing materials were from Oct. 14, 1999, six days after Trump announced he was forming an exploratory committee to run for president as part of the Reform Party.

The hypothetical question the Clinton aides anticipated was: “Everyone from Warren Beatty to Donald Trump to Cybil Shepherd is contemplating a run for the White House. Do you think this trivializes the importance of the office, and do you feel in any way responsible for that trend?”

“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,” the briefing read. “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.”

Before an interview with journalist Bryant Gumbel, President Clinton was also briefed on a similar question.

The briefing from Oct. 29, 1999, showed that aides expected Gumbel, who was then working for CBS, to ask President Clinton if Trump and other celebrities considering a run for the White House was a reaction to the Clinton administration.

Clinton’s prepped answer did not mention Trump specifically.

“I don’t think what I’ve done has anything to do with such political developments,” Clinton said, according to the document. “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. 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.”

A Trump Birthday Card

President Clinton’s personal secretary, Betty Currie, asked the president’s deputy chief of staff, Karen Hancox, if a birthday letter should be sent to Trump.

“What are you [sic] thoughts on sending a birthday letter to Donald Trump - who turns 50 on June 14. Please forward response to Maureen Lewis who will prepare letter - if you approve. Thanks,” Currie wrote on June 10, 1996.

Three days later, Currie wrote to Lewis, “Cancel letter to Donald Trump. Let me know.”

Also in the documents are records of the Clintons sending Trump an annual holiday card every year from 1995-2000.

Concerned American

“Concerned American” Jeff Rhodes emailed President Clinton about Trump, expressing his concerns about the real estate mogul's plan to run for the Reform Party nomination.

“I am ‘A True Blue Repulican,’” [sic] Rhodes wrote. "If the Reform Party gets into office it will be an end of hard working americans fighting to make it in this "Great Nation" for a piece of that "American Dream"...I am Just A concern[ed] American that feels if this doesn't turn out this nation is doomed to fail and colapse into choas [sic]."

Rhodes’ email went on to say that he would support Elizabeth Dole, the wife of former Kansas Sen. Bob Dole who dropped out of the GOP race in Oct. 21, 1999.

Trump's Views on Trade and Cuba

In a memo from chief of staff Peter Scher to President Clinton on what issues New Yorkers are most concerned with, Cuba came up as a topic of discussion.

“The issue of trade relations with Cuba has drawn local media attention,” Scher wrote on Feb. 14, 1997. “Donald Trump is among those offering the opinion that the U.S. should hasten a transition to a free economy in Cuba through instant investment and development.”

Today, Trump believes that the U.S. should normalize diplomatic and economic relations with Cuba, even saying in a town hall with CNN on March 21 that he would consider opening a hotel in Havana.

Photo-Op With Trump

Included in the documents is a readout of President Clinton’s “photo opportunity” with Trump at Trump Tower in New York City on June 16, 2000. The photo-op only lasted about seven minutes.

ABC’s Shushannah Walshe, Meghan Keneally, Ryan Struyk, John Kruzel, Katherine Faulders and Josh Haskell contributed to this report.