The current president and O.J. Simpson were once buddies. Back in the day, Donald Trump and Simpson hung out together, once in 1993 at a chic Manhattan night spot. Ivanka Trump, 12 years old at the time, was there with her father. Simpson was there with his wife, Nicole. Later that year, Simpson was a guest at Trump's lavish second wedding to Marla Maples. No surprise, Trump's friendship with Simpson soured, but in 2008 he told Howard Stern he wanted to cast Simpson in the ninth season of Celebrity Apprentice. #InsideEdition

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