Who Is Sandra Taylor? Meet the Playboy Model Who Had a 3-Day Fling With Donald Trump

Sandra Taylor, the model who had a "wonderful three-day fling" with President Donald Trump, had nearly ventured into a different vocation before embarking on a modeling and acting career.

In an interview with Nevada Public Radio, the former Playboy model said she wanted to become a mathematician like her father. However, the patriarch's death redirected the trajectory of her life.

The New York native, now 59, entered the modeling industry by working with different publications, including Penthouse. She captured widespread attention when she graced the July 1995 cover of Playboy in a stars-and-stripes bikini, helping to cement her early career.

According to her IMDb page, Taylor played roles in Under Siege 2: Dark Territory, The Princess Diaries and Valentine's Day, ER and Married… with Children, to name a few.

Asked how her careers mutually shaped each other, she explained, "It's been beneficial, being in front of the camera for 30 years. A lot of sommeliers are walking encyclopedias but not particularly outgoing. I love meeting people and performing. At the stadium on Sundays, it's the Sandy show."

Taylor is now a certified sommelier and currently works for the Las Vegas Raiders. In addition, she serves as chief ambassador for Waldorf Astoria Beverly Hills.

"The fans at the stadium are so happy to have higher-tiered wines available to them for game day. It's like they're entertaining in their own living rooms," she said of her Raiders experience.

According to Taylor, she progressed into her current role as she "needed a Plan B" after working as an actress and model for 30 years.

"I always had a wonderful sense of smell & taste & decided to take a few introductory wine courses to see if it interested me. I enjoyed them very much," she told Sommelier Business. "I was attending a big Hollywood Gala & bid on a charity item which was a tour of Barolo & Barbaresco & won."

Taylor continued, "When I went, I had my Aha moment & fell in love with the history, the grapes, the terroir, the people & the rest is history! I progressed into this role because my restaurant closed during Covid and my dear friend Mark Davis who is the owner of the NFL team The Raiders was building a new stadium and I presented him with the wonderful idea of bringing a premium wine program to the higher level Suite holders."

Davis reportedly "loved the thought of it." After trying it during several games, it quickly caught the attention of wine enthusiasts.

Elsewhere in the conversation, she said the best part of her job "is being able to share the absolute joy of wine and be able to share it with people. After being an actress for 30 years, I feel I'm a good presenter and enjoy sharing it with people."

As for the worst part, Taylor admitted, "[It] could ONLY be standing on my feet for such a long period of time."

Taylor is married to David O'Connell, with whom she shares two children, Shelby and Jackson.

Model Torrie Wilson confirmed in a January 2025 Facebook post the family lost their home in the Palisades wildfire at the time.

"They lost everything," she wrote. "I've been really struggling these past few days, feeling helpless being so far away. But I CAN help by asking YOU to share in ANY way you can. Even $5 means the world. If you have it in your heart, please help me help her & her family. Their kindness, optimism, and genuine friendship has gotten me thru some of my darkest days. Now I hope I can help do the same for them.❤️🙏🏽."

In a 2015 interview with Page Six, Taylor was asked whether Trump was a good lover.

"Omigosh, he was great [in bed]," she said. "I think he'd be a terrific president."

She disclosed she had a three-day fling with the POTUS shortly after his divorce from his first wife, Ivana.

More than a decade after the 2015 interview, Taylor admitted she regrets mentioning the story as she endured unwarranted backlash as a result.

"No good came out of it. Only negative came out of it," she told Daily Mail. "I was really just trying to say he's a great guy and he was great to me when I needed someone most after my dad's death. Also, when you date someone when you're 19, and it's 35 years later, you say to somebody, 'Well, where were you 35 years ago?' Times were so different then."

According to Taylor, the article cast her in an unfavorable light.

"People are going to want to judge, and people are going to want to hate. I guess that's what comes with the territory. That is why I've been mute about it really," she continued.