Who Would've Thought? Trump and Clinton Were Once Friends
It might be hard to believe now, especially after the heated 2016 presidential election, but Donald Trump and Hillary Clinton weren’t always political adversaries. Believe it or not, they were once on pretty friendly terms. In fact, Hillary even attended Donald’s 2005 wedding to Melania Trump. Back then, the Clintons and the Trumps actually got along pretty well. It's almost like watching two old friends turn into rivals over time, isn’t it?
Wedding Day Memories: The Clintons at the Trumps’ Big Day
Photos from Donald and Melania’s star-studded wedding show Hillary and her husband, Bill Clinton, posing happily with the newlyweds. In one picture, you can see them laughing at something Donald said. Bo Dietl, a guest at the wedding, told NPR about the scene. “When Donald and Melania came out to greet the guests, I saw Hillary going over and… kissing them. She was very pleasant with him,” he recalled. It was a moment that seemed to capture a different era in their relationship.

Bill and Hillary at Donald and Melania’s wedding.
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Money Talks: The Clintons and the Trumps’ Financial Ties
The Clintons had good reasons to appear friendly with the Trumps. Over the years, Donald contributed more than $4,000 to Hillary’s Senate campaigns and at least $100,000 to the Clinton Foundation, according to Politifact. But let’s not kid ourselves—Donald’s generosity might have been more about strategy than friendship. Gwenda Blair, author of The Trumps: Three Generations of Builders and a Presidential Candidate, told NPR that the former President’s friendships are “always transactional and only transactional.” She added, “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.”
Michael D’Antonio, another Trump biographer, painted a similar picture of the real estate tycoon’s personal relationships. “Outside of family, it seems like every move he makes is calculated to benefit him in some way, either financially or politically,” he explained. “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.”
Pop Culture Parallels: Taylor Swift and Kanye West?
D’Antonio even drew a pop culture comparison that felt eerily fitting. “There is a Taylor Swift-Kanye West parallel when it comes to Hillary and Trump,” he noted. “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.” It’s like watching a soap opera unfold in real life, isn’t it?


