Examining The Clinton-Trump Relationship Before Election Season Started

Hillary Clinton attended Donald Trump's third wedding. Trump has contributed to Clinton's past campaigns and her husband's foundation. Does this mean that, before this election, they were friends?

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Donald Trump and Hillary Clinton have been appearing like mortal enemies on the campaign trail. But it wasn't always that way. Back in the day, Clinton and Trump socialized and even looked like, dare I say, friends. Here's NPR's Sam Sanders.

SAM SANDERS, BYLINE: OK. Google the words Donald Trump Hillary Clinton wedding. What do you see? Pictures of the Clintons and the Trumps at Trump's wedding to Melania in 2005. There's this one with Bill grabbing Donald's shoulder, another one with Donald's arm around Hillary, Bill's hand around Melania. And they're all smiling. It's just smiles on smiles on smiles. If you just saw those pictures, you'd swear that Donald and Hillary are best friends. Clearly, we have to hear from someone who was at that wedding.

BO DIETL: The name Bo - B-O - and the last name's Dietl. I'm the owner and founder of Beau Dietl Associates.

SANDERS: I caught Bo last week. He was in the Hamptons vacationing, so he talked to me on his cell phone. And the audio quality is not the best. Anyway, Bo has been a friend of Trump's for a while. And he was there when the Clintons and the Trumps got all snuggly.

DIETL: And when Donald and Melania came out to greet a lot of the guests, I saw Hillary going over and, you know, kissing - you know, kissing them. And she was very pleasant with him.

SANDERS: Now, Dietl says, at the same wedding, Hillary was also really friendly with him. But here's the thing to know about Bo. He's a Fox News contributor, and he's said some not-very-nice things about Hillary Clinton. So he was surprised when their meeting at the wedding went as well as it did.

DIETL: I was still talking to Shaq O'Neal, and he was showing me his deputy sheriff badge or something. I hear from across the room - Bo, Bo. And it was Hillary Clinton. And she didn't really know me that well. And she acted like I was her best friend.

SANDERS: She kissed you, you said?

DIETL: Yeah, she ran across. And she gave me a kiss on the cheek, and I kissed her back.

SANDERS: So it seems Hillary Clinton, like lots of politicians, can be friendly with people she isn't exactly friends with - no biggie. But what about Donald Trump? That calls for an expert.

GWENDA BLAIR: Gwenda Blair, author of "The Trumps: Three Generations Of Builders And A Presidential Candidate."

SANDERS: Blair has actually written two books about the Trumps. I talked to her via Skype. She says Donald Trump's friendships are not like yours and mine.

BLAIR: They're transactional. They're always transactional and only transactional.

SANDERS: And it was a two-way street. The Clintons didn't just attend Trump's wedding. Over the years, Donald Trump has given more than $4,000 to Hillary Clinton's Senate campaigns and more than $100,000 to the Clinton Foundation according to PolitiFact. This is just something Trump does.

BLAIR: He surrounds himself with people he perceives as winners - celebrities, sports stars, actors, entertainers. He wants to be, you know, literally in the picture with them.

SANDERS: Michael D'Antonio is also a Trump biographer. I talked to him on Skype, too. And he says, for Trump, just about everything he does is strategic.

MICHAEL D'ANTONIO: Outside of family, it seems like every move he makes is calculated to benefit him in some way, either financially or politically.

SANDERS: D'Antonio says the relationship between Hillary Clinton and Donald Trump, in spite of the wedding photos and the contributions, it was pretty thin.

D'ANTONIO: You know, this is a guy who literally produces his life. So much of what we see is fiction. It's a play, a drama of manners.

SANDERS: And D'Antonio says relationships with people at Trump's level - at the Clinton's level - they're just different. They are not like you and me. They're more like other famous people.

D'ANTONIO: There is a Taylor Swift-Kanye West parallel when it comes to Hillary and Trump. They will go at each other viciously, and then I will not be surprised when I do see them reconcile and smile and shake hands at some party in the future.

SANDERS: Well, that could happen at some point, but definitely not before November. Sam Sanders, NPR News.

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