This Famous Singer Reportedly Almost Stole Marla Maples From Donald Trump

Marla Maples endured her fair share of media attention while married to Donald Trump in the mid-1990s, but public fascination with their relationship blossomed anew with the 2019 release of previously confidential FBI documents. According to Inside Edition, the documents revealed that Donald was not the only famous man in Maples' orbit in the early 1990s: singer-songwriter Michael Bolton once stood by her side instead. Two decades after Maples and Donald divorced, it's surprising to learn that their opulent New York City wedding and equally captivating marriage might've never happened.

Donald Trump's multiple marriages have never failed to capture an audience, including his short-lived union with Maples. Their relationship started as an affair while he was still married to his first wife, Ivana Trump, and was marked by dramatic ups and downs from Day One. Most notably, Maples earned the ire of the first Mrs. Trump, and those negative feelings continued for the remainder of Ivana's life. In a 2017 interview with CBS correspondent Jim Axelrod, Ivana insisted, "I don't talk about her." Ivana then blamed Maples for the dissolution of her marriage to Donald. 

However, there are two sides to every story, including Maples' relationship with Bolton. Although the singer himself has remained silent on the subject, both Maples and Donald have shared the true nature of this supposed affair several times over the years. 

Marla Maples' former publicist Chuck Jones' now-public testimony alludes to a romantic connection between Maples and singer Michael Bolton, whom she dated during her on-again, off-again relationship with Donald Trump. A Daily Mail article highlights some of the most scandalous parts of Jones' testimony, including his claim that Maples "brought singer Michael Bolton back to her room following Trump's departure from a west coast trip." 

Jones' testimony makes the relationship seem like a clandestine affair but the connection between Maples and Bolton certainly wasn't a secret to Trump. In 1994, the former president told Vanity Fair about Maples and Bolton dating, describing how the singer's attraction to Maples made him see her value in a new way. According to Trump, the relationship was "an affirmation that the girl has to be great, because the No. 1 singer has fallen for her."

Trump clearly won Maples' affections in the end, but it appears he wasn't content with simply repairing his relationship with the former showgirl. In a segment about Maggie Haberman's book, "Confidence Man," on "Jimmy Kimmel Live!" the eponymous host highlighted an especially amusing part of the Trump-Bolton saga: following his reconciliation with Maples, Trump reportedly treated her to tickets to a Michael Bolton concert. As Kimmel sarcastically explained, "He really showed Michael Bolton by buying two tickets to see him in concert."

Although Chuck Jones' testimony makes Marla Maples' relationship with Michael Bolton seem like infidelity, his description may not be accurate. In fact, the model herself presents a much more innocent perspective on her time with the singer. In 2024, the Daily Mail shared a video of an impromptu interview between Maples and a freelance celebrity photographer, who caught up with her at Los Angeles International airport. When asked about the FBI files and her supposed affair with Bolton, Maples laughed and explained, "He's a dear, dear friend. We dated years ago." She also refuted infidelity rumors by saying, "I was always faithful to Donald [Trump]."

The highly public nature of Maples' marriage to Trump made tabloid rumors commonplace for the model, and the 2019 release of Jones' testimony wasn't the first time she found herself denying claims she and Bolton were an item. In 1998, she dispelled several rumors in New York magazine about her relationship status before her official divorce from Trump. "When I first separated from Donald, they had me back with the guy I dated years ago, Michael Bolton," she said. "They had me doing rendezvous with Kevin Costner, and living with Kathy Lee Gifford. None of which was true."