Donald Trump Had A Complicated Relationship With O.J. Simpson

What do you get when you cross two of the most complicated, highly divisive celebrities of the last three decades? A complicated, highly divisive relationship, of course. Such was the case for the hot-and-cold bond between former President Donald Trump and O.J. Simpson, who weren't the closest of friends but not the worst of enemies. 

While it's unclear how the two public figures first met, it would stand to reason they ran in the same circles as two of the most prominent New York-based celebs of the 1990s. The pair was spotted spending time together in Manhattan in 1993, the same year Trump married his second wife, Marla Maples. Simpson was one of many stars who attended the high-profile event.

However, events over the next couple of decades would cause their relationship to waver. Between Simpson's infamous legal troubles and Trump's transformation from real estate mogul to U.S. president, the pair (or, at the very least, Trump) has gone back and forth on whether or not the two controversial celebrities were still friends.

Public opinion on O.J. Simpson has been particularly divisive ever since his highly publicized 1995 trial where he was tried — and later acquitted — for the murders of his wife, Nicole Brown, and her friend, Ron Goldman. Simpson was later found liable for Goldman's murder and battery of his wife in a 1997 civil trial. Nevertheless, the public was divided between people who believed Simpson guilty and those who believed him innocent. Donald Trump has argued for both.

The not-yet-former president visited the "Howard Stern Show" in November 1995, one month after Simpson was initially acquitted. Trump and Stern discussed the trial's outcome, with Trump acknowledging that he knew Stern believed Simpson to be innocent. The real estate mogul suggested that the blood found in Simpson's Jeep was not a significant amount, saying, "Fifty different people could have planted it. I don't think LAPD is that smart" (via Newsweek).

Less than a decade later, Trump revisited Stern's program in 2008. Simpson was once again brought up, but this time, it was about Trump potentially hiring the ex-football star for his reality series "The Apprentice." Per New York Daily News, Trump told Stern that while NBC "went totally crazy" over the suggestion, Trump didn't follow through with the idea because "I don't like people that kill their wives. Does that make sense? Does that make me a disloyal person?"

For what it's worth, O.J. Simpson's stance on Donald Trump has also changed over the years. While attending Trump's 1993 wedding, Simpson spoke to reporters about the real estate mogul marrying the woman with whom he had cheated on his first wife, Ivana Trump. "I think everybody in the country believes maybe their relationship can work if this relationship can work," Simpson said. (This, unfortunately, would not be the last uncomfortable comment Simpson has made concerning women.) 

Years later, Simpson would be offering advice, not accolades, to Trump. Rather than painting the man he used to call "The Donald" as an inspiration, Simpson treated Trump like someone in dire need of guidance in a June 2023 video the ex-football star posted on X, formerly Twitter. Amidst former President Trump's ongoing legal woes, Simpson cited his own trial experience and said the best legal advice he ever received was to avoid publicly discussing the case. He suggested Trump do the same. 

A little under two months before Simpson died at age 76 following a prostate cancer diagnosis, The Juice gave a subtle nod to his former pal in a statement regarding his health. In another X video, Simpson denied that he was entering hospice care, adding, "I don't know who put that out there. I guess it's like The Donald says, you can't trust the media."