These Eye-Opening Documents Show How Close Donald Trump & The Clintons Actually Were

It's no secret the Clintons and Donald Trump go way back. Believe it or not, the mudslinging between the respective Democratic and Republican frontrunners is actually a rather recent development in their relationship. In 2005, both Bill and Hillary Clinton attended Trump's marriage to his third wife, Melania, and before that, Trump wrote a big check to the Clinton Foundation. But what about the early days during Bill Clinton's two terms as president? That picture has just become much clearer. New documents on Trump released by the Clinton Presidential Library show just how close the Clintons and Trump were — and weren't — during Bill's time in office.

About 500 pages were released by the National Archives and published by the Clinton library in response to a FOIA request. The Clintons and the Obama administration were warned in January about the documents pending release and were given the option of trying to keep them under wraps; they didn't. Only three pages of the Trump-related documents were restricted to release from the public. One seems as though it might hold Trump's personal contact information and was in a database among holiday cards.

Many topics come up over the eight years of Trump being mentioned. One of the most interesting was undoubtedly Bill's thoughts in 2000 on a possible Trump presidential campaign. As one staffer put it, Trump had "his eye on the big JOB" long, long ago.

1. Trump For President 2000

Bill was prepping for an interview with Bryant Gumbel and one of the questions he was prepared to answer was what he thought about a potential Trump candidacy. They were even prepared to rebuff that it was Bill's fault because of a "demeaning of the office" that he had contributed to. That's probably the Monica Lewinsky scandal he's hinting at, FYI.

His response? "The political process will sort out the wheat from the chaff. I'm not concerned about it." I guess he should have been. At least he can't be blamed for Trump's ascendancy in 2016.

2. This Was Something They Were Worried About

He also prepped for a similar question at an October press conference in 1999. The administration was really concerned that Bill could be blamed for a Trump-like candidacy. Other topics covered? West Nile Virus, China joining the WTO, and Y2K. They sound so quaint nowadays.

3. Trump's Poll Numbers Were Not So Good

In a political briefing on California — it includes things like when Bill had last visited the state and "hot issues" to be prepared to speak about — the writers mention the upcoming primary elections in the state. They include some polling and guess who is getting about 1 percent of the vote? That would be Mr. Trump. If only we were still seeing similar numbers.

4. Trump Is Scarier Photocopied

The only thing more disturbing than real Trump is photocopied Trump. This is the cover of The Art of The Deal.

5. A Clinton Staffer — Or His Mom — Was Buddy-Buddy With Trump

A copy of the Trump memoir was part of the Clinton Administration collection because a signed copy was gifted to a Clinton staff member. Evidently his mom is "the best." The underline is Trump's.

6. Donald And Bill's "Similar Broad Vision For The Future"

Bill was invited to a charity event that would feature "another national figure," aka Trump, who was being awarded for his "solid investments" in Atlantic City's gaming and hotel industry (that didn't end so well). The invite came from a Tony August, who thought Trump and Bill had a fair bit in common and should meet:

For the record, lest there be any misunderstanding, I am not, in any way in the employ of Donald Trump, directly or indirectly, nor do I speak for him. I'm also not a matchmaker, but if you two don't know each other you should. You have much in common, age, broad vision for the future and most importantly, the resources and desire to make America bigger and better than it already is.

7. Evidently They Did Meet

President Clinton made it all the way to Trump Towers in New York City during the last year of his presidency. At the time, Hillary was running for the open Senate seat from New York.

8. Trump's Gambling Operations

A couple different emails mention Trump's gaming operations, and his relationship with Native American tribes — his competition. Sounds a bit sketchy.

9. He Supported An Opening With Cuba

Included in an email on "hot issues" was Trump supporting instant investment and development in Cuba. That was in 1997, long before Obama moved on the issue.

10. Trump Wanted To Purchase Governor's Island?

After the Coast Guard closed its base on the island, the plan was to sell the island at fair market value by 2002. Evidently Trump was interested. At the very end of his presidency — the very end, Jan. 19, 2001 — Bill designated several parts of the islands as National Monuments.

11. The Clinton Camp Didn't Know How To Handle Trump's Tax Proposals

Trump proposed a 14.25 percent tax on the net worth of wealthy Americans and trusts in 1999. Not income but net worth — normally that's something that can only be touched by the estate tax. Ted Cruz, are you listening? Interestingly, the Clinton camp didn't know what to do with this proposal either. The subject line of the message containing the news story? "We may need guidance on this."

12. Happy 50th? Nah...

A Clinton staffer considered a 50th birthday letter for Donald Trump. It got shut down.

13. Trump's Heart Will Go On

The Clintons chose not to go to a Larry King Cardiac Foundation fundraiser featuring Donald Trump and the great Celine Dion, still riding strong on Titanic, which was released the previous year.

Now the question is whether American politics will go on past this tumultuous primary season. Here's betting on it — just not in Atlantic City.

Images: Clinton Presidential Library