After 15 years of marriage, Ivana Trump filed for divorce on the grounds that Donald's public relationship with Marla Maples was cruel and caused her mental anguish. The court documents further accused Donald of being verbally abusive and demeaning, and while the Daily Beast claimed there were reports of sexual abuse, Ivana said, "The story is totally without merit."

Although Ivana is bound by a confidentiality clause that prevents her from discussing her marriage, she has gotten away with some public comments. Remembering their time together, Ivana said, "Donald might not have been the greatest husband to me, but he was a good father to the kids," and ultimately, his former wife was very supportive of his 2016 presidential bid.

Trump's second wife, Marla Maples, said she saw a softer side to the business magnate, saying, "I saw a vulnerable man." In 1990, Maples gushed to Vanity Fair, stating, "[He is] a genius, adorable, with a little-boy quality [...] I mean, he knows when he's being too cute and he laughs at himself about it." However, by the time the two divorced, things turned sour.

By 1999, Maples revealed that marrying Trump was a mistake. Maples accused Trump of being entirely ego-driven, saying that he pursued her for years, so much so, she recalled, "I couldn't get away ... and, foolishly, I listened to some of his promises." Ultimately Maples said, "Donald was never the man I wanted to marry […] I'm so happy to be away from Donald."

After Maples, Trump began dating supermodel Kara Young, much to her surprise. She said, "I didn't think he was my type, but it just ends up happening." However, things turned sour when Trump made a racist comment about her mother, saying she had gotten her brains "'from her dad, the white side,'" to which Young replied, "'No, don't say that. It's not funny.'"