It may be difficult to imagine, but Donald Trump and O.J. Simpson were friends at one point.
The pair was often seen together on nights out in the 1990s, before one became an accused killer and the other became president of the United States.
In October 1993, Trump and Simpson were spotted together in a chic Manhattan night spot, accompanied by a then-12-year-old Ivanka Trump and Simpson’s then-wife, Nicole Brown Simpson.
The same year, Simpson was a guest at Trump’s lavish second wedding to Marla Maples.
“I’m excited to see that they are going to do it,” Simpson said in an interview at the time. “You know, I’ve been around them, they’ve gone through a lot of turmoil and I think everyone in the country believes that maybe their relationship will work.”
Just six months later, Nicole and her friend Ronald Goldman were butchered to death, and Simpson was the prime suspect.
Despite his acquittal in the murders, Simpson's friendship with Trump soured.
But in 2008, Trump told radio personality Howard Stern that he wanted to cast Simpson in the ninth season of Celebrity Apprentice.
But NBC balked at the idea, and Trump never made the offer.