Donald Trump Almost Lost Marla Maples to A Famous Singer During Their Early Dating Days

Donald Trump was smitten by Marla Maples, then famous actress/model while he was still married to his first wife Ivana Trump. But, according to 2019 FBI documents obtained by Inside Edition, Trump lost Maples to singer/songwriter Michael Bolton. The FBI file detailed multiple incidents that hinted towards Maples' alleged hookup with Bolton in Trump's absence. 

Maples' former publicist Chuck Jones, who was jailed in 1999 for stealing her nude photographs and dozens of her shoes, testified during the investigation about the alleged affair. The dossier stated that Maples "had bought singer Michael Bolton back to her room following Trump's departure for a West Coast trip." And apparently, the fling was no secret to Trump. 

The then-real estate magnate admitted to knowing about the affair in a 1994 interview with Vanity Fair. Surprisingly, Trump saw it as a way of valuing Maples so much more, saying, Bolton's growing attraction for Maples gave him "an affirmation that the girl has to be great because the No. 1 singer has fallen for her." And instead of giving up on her, Trump won her affections over Bolton. 

Though Jones's testimony made her relationship with Bolton seem like infidelity, Maples' side of the story painted a different picture. Daily Mail shared a video of Maples' impromptu interview with a freelance celebrity photographer who caught up with her at the Los Angeles airport, asking about the FBI files and Jones' testimony. The now-60-year-old admitted, "[Bolton] is a dear, dear friend. We dated years ago," adding that she "was always faithful" to Trump. 

However, her relationship with the entrepreneur-turned-politician was highly public in nature. And because of this, she could barely escape the rumors surrounding her equation with Bolton. Jones's testimony wasn't the first time the reports of her alleged affair surfaced. In 1998, before her official divorce from Trump, she dispelled the same rumors published in New York magazine. "When I first separated from Donald, they had me back with the guy I dated years ago, Michael Bolton," Maples addressed the allegations, adding that the media also had her "doing rendezvous with Kevin Costner, and living with Kathy Lee Gifford. None of which was true."

She met Trump in 1984 and throughout her dating period, she succumbed to allegations of being a homewrecker and labeled a 'mistress' since he was still married to Ivana. However, during an ABC News podcast, Journeys of Faith with Paula Faris, Maples said, "I never considered myself a mistress. I mean, that's the truth." But since he was already married, the journey to becoming his second wife wasn't an easy one. 

She recalled Trump reassuring her parents that "I'm going to marry your daughter one day.'" Following this, she wished everything to go as it was meant to be, "Every step of the way, I was praying, 'God, please be in this. Please be in this. I do not want to be part of breaking anything up that has a chance.'" 

However, their relationship lasted from 1993 to 1999 and she acknowledged that "it didn't happen" the way she imagined it to be. But, "Everything had to happen in the way that it did to bring us to where we are now."