In 1993, former President Donald Trump married his second wife, Marla Maples, amid divorce proceedings with his first wife, Ivana. During this time, OJ Simpson, who was running in high-profile circles, offered some relationship advice to Trump. He noted the cheating that had led to Trump’s divorce from Ivana and suggested that if their relationship could work, maybe others could too.

After Trump divorced Ivana in 1990 and married Marla Maples in 1993, OJ Simpson was arrested for murder the following year. Their relationship took a dramatic turn after OJ’s conviction in 1995. Trump publicly criticized OJ, despite the latter being acquitted of the charges related to the murders of his ex-wife Nicole Brown Simpson and her friend. Trump held on to his belief in OJ’s guilt, even mentioning it in interviews about OJ’s potential appearance on his reality TV show.

OJ Simpson faced financial liability for the deaths of Nicole Brown Simpson and Ronald Goldman in a civil trial, where he was ordered to pay up to $33.5 million but never did. Trump initially argued for OJ’s innocence, suggesting that evidence could have been planted by many different people. However, Trump later shifted his stance, expressing doubts about the LAPD’s intelligence and the significance of the evidence against OJ.

In 2023, OJ Simpson once again offered advice to Trump, this time regarding the legal troubles the former president faces. He advised Trump to avoid discussing his cases publicly, especially on social media where Trump has been vocal. The last time OJ mentioned Trump was to dispel rumors that he was in hospice care, sharing Trump’s sentiment of mistrusting the media.

The relationship between Trump and OJ has seen many shifts, from mutual socializing in high-profile circles to public criticisms and doubts about OJ’s innocence. Despite their complicated history, OJ remained vocal about Trump’s legal issues and advised him to handle his cases discreetly to avoid further complications. Both figures have faced their share of legal challenges and public scrutiny over the years, adding to the complexity of their dynamic.

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