Where Are 16 ‘Amazing Race’ Winners Now?

Victor and Tammy Jih
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Victor and Tammy Jih in Season 14

Rob Frisbee and Brennan Swain became the inaugural winners of The Amazing Race two decades ago, crossing the finish line ahead of all other competitors in the CBS series’ Season 1 finale, which aired in December 2001.

The anniversary didn’t pass Swain by. The lawyer, who says he’s still “best of friends” with Rob, marked the milestone on Instagram April 8, the 20th anniversary of the end of his Race. “Twenty years later, I can look back and realize what a life-changing experience it was,” he wrote, reflecting on his time on the globe-trotting reality competition. “Sure, being on TV was great. But it was the actual race and travel that affected me on a greater level.… It’s difficult to put into words how lucky I was to be a part of that first cast.”

With so much Amazing Race history behind us—and Season 33 fast approaching—we’re checking in with 16 past winners, starting with more details about Swain and Frisbee.

The Amazing Race, Season 33 Premiere, Wednesday, January 5, 2022, 8/7c, CBS

Rob Frisbee
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Rob Frisbee (Season 1)

Frisbee is a lawyer at Connolly & Finkel in Encino, California, where he specializes in general corporate and transactional matters. He has a son, Max, with Carman Knight, the director of global publicity for Walt Disney Studios.

Brennan Swain
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Brennan Swain (Season 1)

Swain is also a lawyer, focusing on patent and trademark law, and he enjoys snowboarding, surfing, bicycling and—believe it or not—obstacle-course racing. He’s also the godfather of Frisbee’s son.

Alex Boylan
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Alex Boylan (Season 2)

Boylan was one of the producers of Prime Video’s World’s Toughest Race: Eco-Challenge Fiji. These days, he hosts The College Tour, a docuseries about college campuses.

Reichen Lehmkuhl
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Reichen Lehmkuhl (Season 4)

Lehmkuhl, who dated Lance Bass and appeared on the reality show The A-List: New York after his Race, is the president and cofounder of LeaseLock, billed as “the world’s leading insurtech platform for real estate.”

Chip and Kim McAllister
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Chip & Kim McAllister (Season 5)

This married couple are the namesake of McAllister Real Estate in Orange County, California, where they “execute [their] win/win strategies and experience” with each client.

Tyler McNiven

Tyler McNiven (Season 9)

McNiven cofounded the meal kit delivery service Sun Basket, and last year, he and his brothers took over ownership of Buck’s, a restaurant in Woodside, California, following their parents’ retirement.

Tammy and Victor Jih
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Tammy & Victor Jih (Season 14)

This brother-and-sister duo are both lawyers: She works for Alphabet, Google’s parent company, and he works for the Los Angeles law firm Wilson Sonsini.

Josh Kilmer-Purcell and Brent Ridge
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Josh Kilmer-Purcell & Brent Ridge (Season 21)

This couple, married for eight years now, own Beekman Farm, a goat farm in Sharon Springs, New York, and Beekman 1802, a skincare brand. A decade ago, Kilmer-Purcell and Ridge starred in the Planet Green reality series The Fabulous Beekman Boys.

Bates and Anthony Battaglia
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Bates & Anthony Battaglia (Season 22)

These hockey-playing brothers just opened Teets, a mobster-themed bar in Raleigh, North Carolina. They named the establishment after their grandfather Sam “Teets” Battaglia, an associate of Al Capone.

Jason Case and Amy Diaz
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Jason Case & Amy Diaz (Season 23)

Diaz and Case tied the knot in 2015, and they welcomed their fourth child, a daughter named Jaclyn, earlier this year. Diaz, a former beauty queen, also works as a motivational speaker and a pageant coach.

Jessica and Cody Nickson
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Jessica & Cody Nickson (Season 30)

This pair wed in 2018 and now have two kids together. Jessica is the owner of the apparel brand it’sNOMB (which stands for It’s None of My Business), while Cody is the author of The Last Fitness Strategy: Lose the Fat for Good.