Sandra Taylor is back in the spotlight after old comments about President Donald Trump’s love life resurfaced and sparked fresh buzz online.
The former Playboy model, actress, and wine industry professional once made headlines for admitting she had a brief three-day romance with Trump years before he entered the White House. But while the comments drew plenty of attention, Taylor has since made it clear that speaking out came with a heavy price.
Long before she built a career in front of cameras, Taylor had a very different dream. She once said she wanted to follow in her father’s footsteps and become a mathematician. But after his death, her life took a different turn — one that pushed her toward modeling, acting, and eventually a high-profile career in hospitality.
Taylor, a New York native, found fame in the modeling world after appearing in major men’s magazines, including Penthouse. Her profile rose even higher when she landed the July 1995 cover of Playboy wearing a stars-and-stripes bikini, a moment that helped cement her image during the peak of her career.
She later expanded into Hollywood, picking up roles in films and television shows including Under Siege 2: Dark Territory, The Princess Diaries, Valentine’s Day, ER, and Married… with Children. Over the years, Taylor built a career that stretched far beyond modeling, proving she had staying power in multiple corners of the entertainment business.
But her life did not stop there.
After decades in the spotlight, Taylor reinvented herself once again and moved into the wine world. She became a certified sommelier and now works with the Las Vegas Raiders while also serving as chief ambassador for Waldorf Astoria Beverly Hills. Taylor has said she fell in love with wine after taking a few courses and later visiting Italy, where she had what she described as an “aha” moment.
She has spoken warmly about her current job, saying she loves introducing people to premium wines and bringing that experience into game-day culture. According to Taylor, the move into hospitality became her Plan B after spending roughly 30 years in modeling and acting.
Off the job, Taylor is also a wife and mother. She is married to David O’Connell, and the couple shares two children, Shelby and Jackson. Her family also reportedly suffered a devastating loss when their home was destroyed in the Palisades wildfire, adding yet another painful chapter to her personal story.
Still, the comments that continue to follow her are the ones involving Trump.
In a 2015 interview, Taylor did not hold back when asked about the president, famously saying he was “great” in bed and adding that she thought he would make a terrific president. She said their brief fling happened after Trump’s divorce from Ivana, long before he became one of the most scrutinized men in American politics.
For many conservatives, the story reads less like scandal and more like another example of Trump’s larger-than-life persona refusing to fade, no matter how many years pass. But for Taylor, the media storm that followed was anything but flattering.
More recently, she admitted she regretted ever talking about the relationship at all.
Taylor said the fallout brought her nothing positive and only opened the door to criticism and judgment. She explained that she had only meant to say Trump had treated her well during a painful period in her life following her father’s death. Instead, she felt the story was twisted into something far more damaging.
She also pointed out that the relationship happened decades ago, when she was just 19, and suggested that people looking at the situation through a modern political lens were missing the reality of the time.
That, she said, is why she has mostly stayed quiet ever since.
Even so, the resurfaced remarks are a reminder that when it comes to Trump, even the oldest stories can explode back into the headlines. And for Sandra Taylor, one candid interview ended up becoming the kind of media baggage that never quite disappears.
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Thats wh
I don\’t believe anything you say about our President.