Some Amazing Race winners became lawyers at Google, others turned $1M into a goat farm empire

Every Amazing Race winner pocketed $1 million — but what they did with the money, and the years that followed, varies wildly. Some went back to courtrooms and law firms. Others built goat-milk empires, launched tech companies, or earned Emmy nominations in TV production. From the original Season 1 champs to the Season 38 brothers who made history, here is every Amazing Race winner, their season, and where life took them next.

Key takeaways

• Rob Frisbee and Brennan Swain (Season 1) are still best friends and still lawyers — Brennan specialises in IP law, Rob writes for film and TV on the side.
• Tammy and Victor Jih (Season 14) are arguably the highest-achieving winners: both Harvard Law graduates, with Tammy now at Google and Victor a partner at a top LA firm.
• Josh Kilmer-Purcell and Brent Ridge (Season 21) used their $1M to pay off a goat farm and build Beekman 1802 into a lifestyle brand sold in Target and Anthropologie.
• Jag and Jas Bains (Season 38, 2025) are the most recent winners, becoming the first Sikh-Punjabi team ever to win the show.
• Winners include lawyers, a drone inventor, a Broadway actor, a motivational speaker, and a pair who host a Dungeons & Dragons game — the post-Race paths are as diverse as the Race itself.

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How this list was compiled

Each winner's season, relationship type, and post-Race life comes from CBS official records, Wikipedia season pages, and verified entertainment reporting, including TV Insider, Newsweek, Yahoo Entertainment, and Gold Derby. Winners are listed in chronological season order, from Season 1 (2001) through Season 38 (2025).

Summary table

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Season 1 (2001)

Rob Frisbee & Brennan Swain

• Relationship: Best friends/lawyers
• Season aired: September–December 2001
• Season: 1
• Nationality: American

Lawyers and best friends Rob Frisbee and Brennan Swain won Season 1, claiming the first $1 million prize in Amazing Race history. Over the season's 13 legs, the duo won 5.

Frisbee is a lawyer at Connolly & Finkel in Encino, California, while Swain focuses on patent and trademark law. Rob, the Harvard-trained lawyer, also writes for film and television. Swain is Frisbee's son's godfather.

Season 2 (2002)

Chris Luca & Alex Boylan

• Relationship: Lifelong friends
• Season aired: March–May 2002
• Season: 2
• Nationality: American

Chris and Alex won the race, narrowly beating Tara and Wil into second place in San Francisco—the closest finish in the show's history.

Chris has stayed away from the public eye. Alex married Katie Erlandson in 2019, works as an Emmy-nominated television producer, and has hosted Amazon's The College Tour since 2020.

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Season 3 (2002–03)

Flo Pesenti & Zach Behr

• Relationship: Friends
• Season aired: October 2002–January 2003
• Season: 3
• Nationality: American

Flo Pesenti and Zach Behr joined The Amazing Race Season 3 as friends from New York. At the time, Flo was a Public Relations Associate, and Zach was a Production Assistant.

Flo became Director of Public Relations at Tod's (2005–2009) and Gucci (2010–2016). She is now Vice President of Public Relations at MacAndrews & Forbes.

Season 4 (2003)

Reichen Lehmkuhl & Chip Arndt

• Relationship: Married couple (later divorced)
• Season aired: May–August 2003
• Season: 4
• Nationality: American

Reichen and Chip made history as the first LGBT racers and team to win The Amazing Race. The duo split six months after the show wrapped in 2003.

Reichen went to law school in 2013 and founded his own company, LeaseLock. Chip became very active in the LGBT community after his win, becoming the first openly gay man to cast an electoral vote in Florida, and has worked as the EVP of Flimp Communications since 2013.

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Season 5 (2004)

Chip & Kim McAllister

• Relationship: Married couple
• Season aired: July–September 2004
• Season: 5
• Nationality: American

Married parents Chip and Kim were the first Black winners of The Amazing Race and the oldest winners at the time, with an average age of 45.

The couple began touring as motivational speakers following their win. They have three children and founded PeopleStar FilmWorks, and they work as realtors for The McAllister Real Estate Group.

Season 6 (2004–05)

Freddy Holliday & Kendra Bentley

• Relationship: Engaged models (later married, then divorced)
• Season aired: October 2004–January 2005
• Season: 6
• Nationality: American

The engaged models from Miami had the largest age gap for a winning team — Holliday was nine years Bentley's senior.

Freddy and Kendra tied the knot in 2005 and had two sons together, but have since divorced; Freddy married his second wife, Ginger, in 2015. Kendra continues to work as a model and has a solid Instagram following.

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Season 7 (2005)

Uchenna & Joyce Agu

• Relationship: Married couple (later divorced)
• Season aired: March–May 2005
• Season: 7
• Nationality: American

Despite begging for money and flights and finishing last in the penultimate non-elimination leg, the couple managed to beat "Survivor's" Rob & Amber to win The Amazing Race 7. Uchenna and Joyce divorced in May 2011.

Uchenna moved into public speaking and acting, starring in the films Krazy Meets Karma and Destinies in 2019.

Season 8 (2005) — The Linz Family

Nick, Alex, Megan & Tommy Linz

• Relationship: Siblings
• Season aired: September–December 2005
• Season: 8 (Family Edition)
• Nationality: American

The sibling quartet was the first and only winners of the "Family" Edition of the race, which proved less popular than the two-person team format.

After their win, the siblings gave their parents half of their prize money. All of the siblings are now married and have children.

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Season 9 (2006)

BJ Averell & Tyler MacNiven

• Relationship: Best friends
• Season aired: February–May 2006
• Season: 9
• Nationality: American

The bohemian best friends met during a Semester at Sea program before winning Season 9. Friends Eric Sanchez and Jeremy Ryan finished in second place.

Tyler MacNiven co-founded the meal-kit delivery service Sun Basket, and he and his brothers later took over ownership of Buck's, a restaurant in Woodside, California, after their parents retired.

Season 10 (2006)

Tyler Denk & James Branaman

• Relationship: Friends/models
• Season aired: September–December 2006
• Season: 10
• Nationality: American

Tyler and James were models from Los Angeles and were the first winners to have overcome substance abuse problems before their stint on the race.

Both pursued careers in entertainment and public life after the show, using their platform to speak about sobriety and recovery.

Season 11 — All-Stars (2007)

Eric Linz & Danielle Turner

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• Relationship: Dating couple (rivals-turned-partners)
• Season aired: February–May 2007
• Season: 11 (All-Stars)
• Nationality: American

Eric and Danielle were rivals during Season 9 and returned for the All-Stars as a dating couple—and this time they won.

The pair largely retreated from public life after their win. Eric Sanchez and Danielle Turner beat out Beauty Queens Dustin Seltzer and Kandice Pelletier, who finished second.

Season 12 (2007–08)

TK Erwin & Rachel Rosales

• Relationship: Newly dating couple
• Season aired: November 2007–January 2008
• Season: 12
• Nationality: American

Newly dating couple TK Erwin and Rachel Rosales won Season 12, while father and daughter Ronald and Christina Hsu finished in second place.

The couple kept a low public profile after their win, avoiding the reality TV circuit that captured many of their fellow winners.

Season 13 (2008)

Nick & Starr Spangler

• Relationship: Siblings
• Season aired: September–December 2008
• Season: 13
• Nationality: American

Nicholas "Nick" Spangler and Emily "Starr" Spangler are brother and sister and the official winners of The Amazing Race 13.

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Nick became a full-time actor, most recently starring in Tootsie on Broadway, and got married in 2013, welcoming a son, Nathan, two years later. After overcoming a lymphoma diagnosis in 2010, Starr married Tyler Rey in 2013 and works for Facebook's Change Management and Global Recruiting Operations.

Season 14 (2009)

Tammy & Victor Jih

• Relationship: Siblings
• Season aired: February–May 2009
• Season: 14
• Nationality: American

Tammy and Victor Jih, siblings with Harvard law degrees, won The Amazing Race Season 14. This brother-and-sister duo is both lawyers: Starr works for Alphabet (Google's parent company), and Victor works for the Los Angeles law firm Wilson Sonsini.

After 11 years at the company, Tammy is now Google's privacy and legal director. Victor Jih is a partner at the Los Angeles law office of Irell & Manella, and he co-teaches the Ninth Circuit Appellate Practice Clinic at UCLA.

Season 15 (2009–10)

Meghan Rickey & Cheyne Whitney

• Relationship: Dating couple (later married)
• Season aired: September 2009–January 2010
• Season: 15
• Nationality: American

Meghan and Cheyne were dating in San Diego when they won Season 15. The pair, who had been dating for five years when they won, tied the knot in May 2011 and have two children. Meghan works in PR for True Photography while Cheyne is senior manager at the Rescue Social Change Group in San Diego.

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Season 16 (2010)

Dan & Jordan Pious

• Relationship: Brothers
• Season aired: February–May 2010
• Season: 16
• Nationality: American

Dan and Jordan Pious won Season 16 as the first-ever brother duo to claim the $1 million prize. The brothers built their strategy around teamwork and communication and maintained a relatively private life after the show.

Season 17 (2010)

Nat Strand & Kat Chang

• Relationship: Best friends/doctors
• Season aired: September–December 2010
• Season: 17
• Nationality: American

After 17 seasons, this doctor duo made Amazing Race history as the first all-female team to win.

Both Nat and Kat continued their medical careers after winning. Nat is an anesthesiologist, and the duo used their win to raise awareness for Type 1 diabetes, as Nat managed the condition throughout the race.

Season 18 — Unfinished Business (2011)

Kisha & Jen Hoffman

• Relationship: Sisters
• Season aired: February–May 2011
• Season: 18 (Unfinished Business)
• Nationality: American

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Kisha and Jen Hoffman won The Amazing Race 18 — also known as Unfinished Business — in which returning teams competed for US$1,000,000. The siblings redeemed themselves after their embarrassing elimination in Season 14, when a bathroom break had caused them to finish last.

The Hoffman sisters remained close after the race. Both have maintained private lives, with Kisha focusing on fitness and personal development.

Season 19 (2011–12)

Ernie Halvorsen & Cindy Chiang

• Relationship: Engaged couple (later married)
• Season aired: September 2011–December 2011
• Season: 19
• Nationality: American

Ernie and Cindy, engaged at the time, had won only two previous legs before taking the grand prize on The Amazing Race. Cindy Chiang and Ernie Halvorsen married in 2012.

Cindy currently works as the head of industry, home and fashion brands at Google. Ernie is a social impact business investor with Thread International.

Season 20 (2012)

Rachel Brown & Dave O'Leary

• Relationship: Married couple
• Season aired: February–May 2012
• Season: 20
• Nationality: American

US Army officer Dave O'Leary and his wife, Rachel, dominated their season, winning a record eight legs.

Dave, a retired Army colonel, and Rachel, a flight attendant, both continued their careers after the Race. Their military-honed discipline was widely credited for their dominant performance — still the most legs won by a single team in one season.

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Season 21 (2012)

Josh Kilmer-Purcell & Brent Ridge

• Relationship: Life partners (later married)
• Season aired: September–December 2012
• Season: 21
• Nationality: American

The goat farmers were the second gay team to win The Amazing Race and the first to do so after finishing next to last in six previous legs—in fact, they hadn't won a single leg until the very end.

After winning Season 21, Brent and Josh married at their farm and used their cash prize to pay it off. Brent, also a physician, accepted a faculty position at SUNY to teach marketing, while Josh gave up his job to farm full-time. They first started selling goat milk and goat milk soap products and now work with over 50 artisans, with their Beekman 1802 products featured in Target, Disney Resort, and Anthropologie.

Season 22 (2013)

Bates & Anthony Battaglia

• Relationship: Brothers/hockey players
• Season aired: February–May 2013
• Season: 22
• Nationality: American

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The Battaglia brothers, both former professional hockey players, won Season 22 with a combination of athleticism and sharp navigation. They have since opened T*ets, a mobster-themed bar in Raleigh, North Carolina, named after their grandfather Sam "T*ets" Battaglia, an associate of Al Capone.

Season 23 (2013)

Jason Case & Amy Diaz

• Relationship: Dating couple (later married)
• Season aired: September–December 2013
• Season: 23
• Nationality: American

Amy and Jason were boyfriend and girlfriend when they won The Amazing Race in 2013, and tied the knot two years later. They welcomed their fourth child, a daughter named Jaclyn. Amy also works as a motivational speaker and pageant coach.

Season 24 — All-Stars (2014)

Dave & Connor O'Leary

• Relationship: Father & son
• Season aired: February–May 2014
• Season: 24 (All-Stars)
• Nationality: American

Dave and Connor O'Leary returned for Season 24's All-Stars edition after a strong run in Season 22, and this time won the title, completing their redemption arc. Father Dave is a retired Army officer; son Connor, a professional cyclist, continued competing after the Race.

Season 25 (2014–15)

Amy DeJong & Maya Warren

• Relationship: Best friends/scientists
• Season aired: September 2014–January 2015
• Season: 25
• Nationality: American

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Amy DeJong and Maya Warren, both food scientists, brought academic precision to their Race strategy. Maya went on to earn her PhD after the show, and both women returned to their scientific careers, with Maya later appearing in food-industry media as a flavour science expert.

Season 26 (2015)

Laura Pierson & Tyler Adams

• Relationship: Dating (matched on the show)
• Season aired: February–May 2015
• Season: 26
• Nationality: American

Season 26 introduced a blind-date format for some teams. Laura and Tyler were among the matched pairs who went the distance — literally and figuratively — claiming the $1M. Both have kept a relatively low profile post-Race.

Season 27 (2015)

Kelsey Gerckens & Joey Buttitta

• Relationship: Dating journalists (later married)
• Season aired: September–December 2015
• Season: 27
• Nationality: American

Kelsey and Joey, both television journalists, brought on-camera composure to the Race and won Season 27 convincingly. They married after the show and have continued their careers in local and digital media.

Season 28 (2016)

Dana Borriello & Matt Steffanina

• Relationship: Dating couple
• Season aired: February–May 2016
• Season: 28
• Nationality: American

Dana and Matt, both dancers and social media personalities, won Season 28 and are one of the Race's most digitally influential alumni. Matt Steffanina runs a massive YouTube dance channel and has built a major online following for choreography content. The two later parted ways, with each continuing in the entertainment industry.

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Season 29 (2017)

Brooke Camhi & Scott Flanary

• Relationship: Strangers (paired on the show)
• Season aired: March–June 2017
• Season: 29
• Nationality: American

Season 29 featured teams of strangers paired at the start. Brooke and Scott, despite initial friction, outlasted all rivals and claimed the title. Both moved on to quieter lives after the win.

Season 30 (2018)

Cody Nickson & Jessica Graf

• Relationship: Dating couple (Big Brother alums)
• Season aired: January–April 2018
• Season: 30
• Nationality: American

Cody and Jessica, already fan favourites from Big Brother 19, arrived as a power couple and delivered a dominant Season 30 performance. This pair wed in 2018 and now have five kids together. They have remained active on social media, sharing family life with their following.

Season 31 — Reality Showdown (2019)

Colin Guinn & Christie Woods

• Relationship: Life partners / returning racers
• Season aired: April–June 2019
• Season: 31 (Reality Showdown)
• Nationality: American

Colin and Christie first appeared on TAR Season 5, where they placed second to Chip & Kim McAllister. They returned for Season 31's celebrity crossover edition and finally claimed the title. Colin loves to surf and is a drone inventor working with Guinn Partners.

Season 32 (2020)

Will Jardell & James Wallington

• Relationship: Dating couple (later engaged, then married)
• Season aired: October–December 2020
• Season: 32
• Nationality: American

Will and James were boyfriends who got engaged at the finish line after winning the $1 million prize. The couple married on 3 December 2021. Both have appeared on other reality shows: Will competed on Capture (2013) and America's Next Top Model (2014).

Season 33 (2022)

Kim & Penn Holderness

• Relationship: Married couple/content creators
• Season aired: January–March 2022
• Season: 33
• Nationality: American

Married couple Kim and Penn were Amazing Race superfans who ran the game with heart and laughter. At ages 45 and 47, the internet personalities from Raleigh, NC became the oldest couple ever to win.

Kim and Penn are still together and continue running their media empire. They have a company called Holderness Media Productions and continue to share their lives with fans via online videos. The couple used their prize money to pay off taxes, set some aside for their kids' college funds, and donated part of it.

Season 34 (2022)

Derek Xiao & Claire Rehfuss

• Relationship: Dating couple (Big Brother alums)
• Season aired: October–December 2022
• Season: 34
• Nationality: American

After originally meeting in the Big Brother house, Derek and Claire started a relationship and then tried their luck on the Race, coming in first place in the season premiere.

The Big Brother alums took home the $1 million prize on Season 34 in December 2022. The pair later revealed they were relocating from New York City to Los Angeles.

Season 35 (2023)

Greg & John Franklin

• Relationship: Brothers/computer scientists
• Season aired: October–December 2023
• Season: 35
• Nationality: American

These brothers and computer scientists, ages 25 and 27, from New York and Mountain View, CA, won five total legs throughout the competition and never appeared below eighth place. The Season 35 finale aired on 13 December 2023.

After the race, John Franklin got engaged to his girlfriend, Celeste, in 2024. Greg continues to work as a software developer.

Season 36 (2024)

Ricky Rotandi & Cesar Aldrete

• Relationship: Boyfriends
• Season aired: March–May 2024
• Season: 36
• Nationality: American

These boyfriends, both 34 years old and from New York City, won a whopping seven legs throughout the competition and never placed below third at any stage. The Season 36 finale aired 15 May 2024.

Following their win, the couple hosts a recap podcast on their YouTube page.

Season 37 (2025)

Carson McCalley & Jack Dodge

• Relationship: Best friends/gamers
• Season aired: March–May 2025
• Season: 37
• Nationality: American

Best friends and gamers Carson McCalley and Jack Dodge won Season 37, while siblings Han and Holden Nguyen finished in second place, and married parents Jonathan and Ana Towns finished in third place.

After winning Season 37, the best friends continue to run their streaming channel Dweeb Wars. The duo also hosts the Dweeb Town podcast, runs an interactive Dungeons & Dragons game, and reportedly plans to use their Amazing Race prize money to create a board game.

Season 38 (2025)

Jag & Jas Bains

• Relationship: Brothers (Big Brother alums)
• Season aired: September–December 2025
• Season: 38 (European Adventure)
• Nationality: American (Punjabi-Sikh heritage)

Brothers and entrepreneurs Jas and Jag Bains won The Amazing Race 38, becoming the first Sikh-Punjabi team to win the series. On this special Big Brother spin-off season, Jag and Jas had seven first-place finishes — one of the best runs in the show's history.

Season 38 concluded with Big Brother alum Jag Bains and his brother, Jas Bains, crossing the finish line first and winning the $1,000,000 prize. As of late 2025, the brothers are still celebrating their historic win.

FAQ

Who is the most successful Amazing Race winner after the show?

Several winners have built impressive post-Race careers, but Tammy Jih stands out academically and professionally. Both Tammy and her brother Victor graduated from Harvard Law. Tammy is now the privacy and legal director at Google. Meanwhile, Josh Kilmer-Purcell and Brent Ridge turned their $1M into a lifestyle empire — Beekman 1802 products are now sold in Target, Disney Resort, and Anthropologie.

Which Amazing Race team has the most wins ever in a single season?

Dave O'Leary and his wife, Rachel, dominated Season 20, winning a record eight legs—the most leg victories by any team in a single season of the US show.

Did any Amazing Race winners stay together after the race?

Many couples who were together during the race eventually married. Season 30 winners Cody Nickson and Jessica Graf wed in 2018 and now have five kids together. However, some pairs split: Chip Arndt and Reichen Lehmkuhl ended their relationship six months after the Season 4 finale aired.

Who were the first all-female team to win The Amazing Race?

After 17 seasons, doctor duo Nat Strand and Kat Chang made Amazing Race history as the first all-female team to win. Both were practising physicians, and Nat raced while managing Type 1 diabetes, making the win even more significant.

Who is the most recent Amazing Race winner?

The most recent winners are brothers Jas and Jag Bains, who won The Amazing Race 38: European Adventure, which concluded on 10 December 2025. They became the first Sikh-Punjabi team to win the series.

From chasing a million-dollar finish line to building corporate careers or goat farming empires, The Amazing Race has been a launchpad for remarkable second acts. These racers show that the real prize can be the grit, adaptability and vision to build unique lives beyond the show.

We also highlighted facts about The Amazing Race Season 1 cast and where its teams are now. The season's winners, Rob Frisbee and Brennan Swain, remain close friends and continue to work as lawyers more than two decades after their victory.

Several teams faced major changes after the race, including divorces, separations and the deaths of former contestants. Joe Baldassare and Bill Bartek, who finished third, remain together and later returned for The Amazing Race: All-Stars.

Source: Legit.ng