By Tessa Berenson
April 12, 2016

Donald Trump may be critical of Hillary Clinton now, but it’s no secret that the Donald and the Clintons go way back.

Trump defended Bill Clinton on television during a tough time in his presidency. When Bill and Hillary set up the Clinton Foundation, Trump gave at least $100,000. And the Clintons came to Trump’s wedding in 2005.

In fact, according to a recent Harper’s Bazaar profile, Trump still has a photo of himself with the Clintons on display in his living room.

A new document dump from the Clinton Library spanning from the early 1990s to the early 2000s opens a window on the former first couple’s relationship with Trump through the years. It includes serious memos on Trump’s real estate deals and involvement in casinos, but there are some lighter tidbits in there, as well.

Here are the five funniest things we learned from the new Clinton files on Trump.

1. They once thought about sending Trump a birthday card, and then decided against it.

On June 10, 1996, Bettie Currie, then-President Bill Clinton’s personal secretary, sent an email to White House staffer Karen Hancox, which read, “What are you 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.”

The next email included in the document release is from three days later, June 13, from Currie to Maureen Lewis: “Cancel letter to Donald Trump. Let me know.”

2. Trump wrote a rather personal inscription on a copy of “The Art of The Deal” for a Clinton staffer.

Trump inscribed a copy of his book for Mark Middleton, then a White House aide. The Clinton Library released a scan of the inscription, which reads, “To Mark- Best wishes. Your mom is the best,” (yes, ‘the best’ is really underlined), and then Trump’s signature.

3. Was Trump going to rent a summer condo in D.C.?

This one is cryptic. On April 26, 1999, Sean Maloney, then White House Staff Secretary (and now a Congressman from New York), wrote an email to Andrew Mayock, a senior adviser. Titled “Georgetown Summer Sublet,” the email simply reads, “donald trump, maybe.”

Was Maloney suggesting Trump rent an apartment in Georgetown for himself? Or buy an apartment to sublet to someone else? Either way, it’s unclear why Trump would summer in Georgetown when he has Mar-a-Lago.

4. Trump manipulated polls in his favor more than 20 years ago.

It turns out Trump’s obsession with polls isn’t new to this campaign. A 1993 draft of talking points for the Clinton administration about Ross Perot’s national referendum delineates good and bad polling practices, and why Perot’s referendum “should not be taken as an accurate barometer of the American people’s sentiment on these issues.”

One reason? “Some people might vote more than once,” the document says. “Generally, with call-in or mail-in polls, those with strongly held views vote more than once. The National Council cited a Parade magazine mail-in poll in which 21% of respondents sent in more than one response. In one USA Today poll on Donald Trump, three out of every four calls were traced to Trump associates.”

5. Bill Clinton’s staff prepared an answer about a potential Trump candidacy in 1999, and it sounds just like he’s talking about 2016.

A document of interview prep before Clinton sat down with CBS’ Bryant Gumbel for an interview in 1999 poses the potential question of whether Trump or other celebrities running for president would be “demeaning” to the presidency.

“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,” Clinton’s prepared answer reads. “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. … 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.”

Write to Tessa Berenson at tessa.berenson@time.com.

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