Divorces, Babies and Cancer Scares: Checking In With The Amazing Race's Most Memorable Winning Teams

These best friends who met while working at the same law firm in Los Angeles hold the distinction of being The Amazing Race‘s first million-dollar prize winners. And while they don’t still work together all these years later—Brennan is a partner at a Los Angeles film specializing in patent, trademark, and copyright law, while Rob works as an attorney at a different firm in the area and writes for TV and film in his spare time—they have remained as close as ever. According to Brennan’s Instagram, the two spent Thanksgiving 2018 together. Since the Race, Brennan has used his celebrity to help raise money for St. Jude’s while traveling the world, hitting 39 of 50 countries on his bucket list, as he told host Phil Keoghan in an episode of his podcast in April 2019 recorded alongside Rob.

These lifelong BFFs, who met on the school bus heading to their first day of kindergarten, were certain that competing together on TAR would have no negative affect on their brotherly relationship. And it appears they were right, as Alex’s Insta account is peppered with photos of the two spending time together. A few years after winning, Chris, who has no social media presence that we could find, married his long-time girlfriend in 2004 and settled down in Florida, while Alex used his platform to carve out a career in the entertainment industry. After hosting shows like At the Chef’s Table and What’s Cooking with Alex for production company Pineridge Film and Television, he partnered with Survivor contestant Burton Roberts to create production company Around The World Productions, which has produced shows like Around the World For Free, Jeff and Jordan Do America, and Rach to the Rescue for The Rachael Ray Show. He’s worked as a correspondent for CBS This Morning, as well as guest host for VH1’s Big Morning Buzz. He’s since launched the website DreamJobbing.com alongside Burton and Lisa Hennessy, which he describes as “a next generation career platform matching applicants and companies through video technology” on his LinkedIn page.

These two good friends with a mutual attraction to one another that they’d never pursued since meeting in college squeaked out a win in season three while Flo was busy flirting with competitor Drew Riker. Following the Race, Flo dated Drew for seven years before breaking up in 2009. Zach, on the other hand, married longtime girlfriend and documentary film director and producer Elyse Steinberg in 2008 before welcoming a child in 2012. After starting a production career of his own at NBC Sports in 2004, he worked his way through the industry and has been the Vice President at The History Channel since July 2018, according to his LinkedIn. In 2009, he opened up to National Geographic on what he did with his half of the million dollar prize, telling the publication he bought “some new computers and an iPod, which at the time was the latest technology” and put the rest away, investing and saving while taking his wife on “some great trips.” Flo, on the other hand, is currently the vice president of PR at venture capital firm MacAndrews & Forbes. In 2010, she began dating TV anchor, legal commentator, and current Live P.D. host Dan Abrams and, in 2012, gave birth to their son Everett Floyd Abrams. However, they keep mentions of the other to such a minimum that it’s unclear whether they’re still together or not.

These two made history as becoming the first committed gay couple to win The Amazing Race. Sadly, they split up six months after competing. Following their split, pilot and model Reichen made headlines for briefly dating Lance Bass as he dipped his toe in the entertainment industry, guest starring on Frasier, The Young and the Restless and Days of Our Lives, while landing a spot in the cast of Logo’s former reality series The A-List. In 2013, he went to law school and has worked as the CEO of LeaseLock since 2012. Chip, meanwhile, has worked as the EVP of Flimp Communications, a human resources and employee benefits digital communications company, since 2013.

Before this married couple residing in Coto de Caza, Calif (aka the land of The Real Housewives of Orange County) went on The Amazing Race, they’d watched at their information technology company was taken over by their partners, leaving them ousted. After running the race, they began touring as motivational speakers available to “energize and inspire your company to win together as a team,” per their LinkedIn page. They founded PeopleStar FilmWorks alongside their son CJ to “bring their expertise in television and film to your business via corporate video production. They’ve also formed The McAllister Real Estate Group through Coldwell Banker, working as realtors in Orange County.

These two engaged models weren’t exactly fan favorites after Kendra’s insensitive comments about the Senegalese people, but they won nevertheless. They tied the knot on May 27, 2005 and had two children together before divorcing. Freddy’s since remarried, to a woman named Ginger in 2015. Kendra’s appeared to have moved on as well, as her Instagram page is full of date night photos with an unidentified male who seems to be the father of her younger children. She still models.

After winning TAR and returning for All-Stars, where they placed fifth, this married couple called it quits, as Joyce revealed in a 2011 interview, though they are “still great friends.” As Joyce explained, prior to the Race, they weren’t sure if they were going to remain married, but the experience brought them back together for a few more years. Before splitting, they founded a charitable children’s organization in Houston. In 2014, Entertainment Weekly reported that Joyce was working on a memoir, while Uchenna’s LinkedIn highlights his current work as a motivational speaker and managing partner at a Houston-area business development consulting firm.

This team of siblings, Nick, Alex, Megan and Tommy, won The Amazing Race’s first-ever Family Edition (which also featured a pre-Vanderpump Rules fame Stassi Schroeder) and have half their prize money to their parents. In 2015, their mother gave updates on each of her children to Cincinnati Public Radio WVXU. Nick is married with children and had spent eight years living in Manhattan Beach, Calif. before moving back to Cincinnatti. At the time, he was partner at Tripack, a manufacturing company, but was made president in January 2018. Alex is also married and a young father and was working in sales at a food packing company until March of this year, when he joined Nick at Tripack. Megan is also married with a handful of kids, with her mom reporting in 2015 that she was a stay-at-home mom. Youngest son Tommy appears to still be single living in Orange County, Calif. and is currently working as an Aviation Sales Advisor.

These best friends commonly referred to as “The Hippies” were one of the most popular teams to ever compete on TAR. Following the race, Tyler dabbled in film, landing a small role in the movie The Pursuit of Happyness, while opening restaurants in the Bay Area with his brother. After meeting girlfriend Kelly Hennigan in 2012 at a friend’s wedding, he popped the question on their two-year anniversary and they tied the knot on Sept. 26, 2015 after going viral with an epic Save the Date video. They’ve since welcomed a child. BJ, meanwhile, is rather active on Instagram and has carved out an entertainment career, making guest appearances on CSI and Weeds, as well as starring in a handful of indie films.

When these two models who met during a Semester at Sea program won TAR, they were recovering addicts who were rebuilding their lives. Now, James is working as a photographer and is married to art director and model Elaina Bellis. The couple welcomed a pair of identical twin girls, Quincy and Rowe, a little over a year after their first child, Lincoln, was stillborn. Tyler, on the other hand, continued modeling after the race. However, he has zero internet presence following his time on the show, so what he’s up to these days is anybody’s guess. 

These two originally competed on separate teams in season nine, began dating, and were invited back for All-Stars two seasons later, which they went on to win. However, they quickly broke up, citing the distance between them as the main reason. Years later, Eric would admit they had only been dating for two months and were pretty much broken up by the time the race began. Danielle has since married contractor Christopher Stout, given birth to a few adorable babies, and is working as a licensed real estate agent on Staten Island, New York. Eric, on the other hand, is currently living in Deerfield Beach, Fla. According to a Twitter account that hasn’t been updated since 2014, he’s worked as the director of sales for Southern Jet.

This brother and sister team were already living their dreams when they won TAR, with Nick performing off-Broadway and Starr cheering for the Dallas Cowboys. Since the race, Nick got married in 2013 and welcomed a son, Nathan, in 2015, followed by Skye in 2017. Most recently, Nick has been appearing in the musical Tootsie on Broadway. As for Starr, she dated fellow season contestant Dallas Imbimbo once the show ended, though the long distance proved to be too much and they separated. After overcoming a 2010 lymphoma diagnosis, she married Tyler Rey in 2013. According to her LinkedIn page, she’s currently living in the San Francisco area, working as the Senior Manager of Facebook’s Change Management and Global Recruiting Operations.

It was another brother/sister duo who won the million in season 14, with these two lawyers coming out on top. As they told People after winning, they planned to do the responsible thing with their prize money and pay off student loans and lines of credit. After the race, Tammy began working at Google, first as Senior Litigation Counsel before working her way up to her current position, Director, Privacy Legal. She is married to her fellow Harvard Law classmate Mark John Murray. They have two children. Victor, on the other hand, has been working as partner at Los Angeles firm Irell & Manella LLP since May 2015 and co-teaches the Ninth Circuit Appellate Practice Clinic at UCLA. An avid marathon runner, he  appears to be single.

This couple met in elementary school and, after 10 years of friendship, began dating. They’d been together for five years when they won season 15 of TAR. In February 2010, they got engaged and got married a little over a year later, on May 7, 2011. Since then, they’ve settled down in San Diego and welcomed two kiddos, daughter Rumi Holland Whitney in September 2016 and son Mays Rhone Whitney in April 2015. Meghan works as the director of operations and vendor relations at True Photography, while Cheyne is the head coach of the Samurai San Diego baseball team and a senior manager at the Rescue Social Change Group, a behavior change marketing agency that works to improve health outcomes for at-risk audiences.

When these brothers snatched a win, Dan was working as a financial advisor and Jordan was a strategic consultant. These days, Jordan’s LinkedIn page notes that he’s been working for Ulta Beauty for the past two years in the greater Chicago area, stepping into the role of Senior Director Merchandising, Strategy & Insights in April 2019. Dan, meanwhile, has been working as an operations manager at Reebook CrossFit Back Bay in Boston since June 2017. In October 2018, Dan married his wife Jamie, an event that Jordan noted on Instagram “finally” gave him “the sister I always wanted.”

These two doctor friends became fan favorites for being possibly the only team in season 17 to not get mad at one another or anyone else. Since winning in 2010, Nat got married and welcomed two children. She continued to advocate for the diabetes community, as she was diagnosed with Type 1 at 12, sharing her story to help others and raise awareness. Kat is also married with two kiddos. She and Nat remain friends and supportive of one another on social media.

In March 2012, this couple made it official and finally tied the knot. Two years later, they welcomed son Maverick Zhang Halvorsen into the world. When they won TAR, they made a vow to provide sustainable employment opportunities for people in developing markets, which they made good on by investing in Thread International, founded by Survivor alum Ian Rosenberger, and Piece & Co. 

After winning the million dollars, this married couple said that they would be returning to Madison, Wisconsin to resume their regular programming. “We’re going to pay off our mortgage and live life as normal,” Dave told the Journal Sentinel. Sadly, life had other plans and they divorced in June 2013. Rachel has since remarried to Chad Weiss. According to Dave’s Twitter, he’s welcomed a son, Nixon Ames, into the world just this year. With whom, however, remains a mystery.

These two were already well-known when they competed in season 21 of TAR, having been the stars of The Fabulous Beekman Boys, which chronicled the couple’s attempts at taking over the Beekman Farm. A year after winning, they got married on their farm and used their earning to pay off the property, as well as help other small farmers. In 2015, they launched a magazine, The Beekman 1802 Magazine. Josh has written a handful of books, while both have worked at SUNY Cobleskill, as Brent joined the faculty as an adjunct marketing professor. Their lifestlye brand, Beekman 1802, now features food, beauty, home decor and apparel.

These former NHL players and brothers have settled into different lives, post TAR. Bates is the owner of Lucky B’s Bar in Raleigh, North Carolina, while Anthony works as a fireman in the same city who also owns and operates Axes and Ales Raleigh with fellow firefighter Ryan Nelson. The company offers party tours aboard a fire engine.

Winning as mere boyfriend and girlfriend, these two tied the knot in 2015 and soon welcomed two daughters and a son. Their youngest child, Allyson, was born in March 2019. Amy currently works as a motivational speaker and host, while Jason remains the president of Case Snow Management, Inc.

These two friend and Ph.D students were never seen as a real threat by the other teams, allowing them to surprise everyone and win season 25. Since then, they’ve both graduated, with Amy going on to be a food structure scientist at Mars (aka the company behind Snickers, Twix, and every other candy you love) and Maya Warren working as Sr. Director of International Research and Development for Cold Stone Creamery. How sweet!

These two were paired together as a Blind Dating team for season 26 of TAR and somehow went on to win the whole thing. They never went on to date one another, despite the interesting premise that brought them into one another’s orbit. Laura returned to her day job working on Hallmark’s Home & Family, stepping into the role of Executive Producer, Talent in 2017. Tyler, meanwhile, as been working as Chief Operating Officer at CertifID, a real-time identity platform for real estate, mortgage, and title industry professionals to securely transfer bank account bank account information, since March 2018. Both appear to still be single.

When these two competed, they were dating colleagues who both worked for news station KEYT NewsChannel 3 in Santa Barbara, Calif. The two made things official in 2017, tying the knot on August 25, and announced they were expecting their first child in February. “Breaking News: Baby Buttitta coming August 2019!” Kelsey captioned her Instagram post announcing the good news. They both remain in their gigs at KEYT, with Kelsey working as weather anchor while Joey is an anchor and reporter.

When these YouTubers and professional dancers competed in season 28, they were engaged to be married. Sadly, they called it quits in 2016. Dana posted about the split on Instagram, saying she was “devastated” after Matt “left me several weeks ago.” While currently single, the two have continued their dance careers at full force. And Matt likes to post plenty of ab-tastic shirtless photos on Instagram. If you’re into that sort of thing.

These two began dating while also competing on season 19 of Big Brother and their popularity led to CBS seeking them out as racers for season 30 of TAR. They began racing just 11 days after filming on BB wrapped and went on the win the entire thing, making them the first team from another CBS franchise to win The Amazing Race. They got engaged on February 13, 2018 and announced they were expecting their first child that September. They tied the knot on October 13, 2018 in Malibu, with their daughter Maverick entering the world four weeks premature on March 2019.