'The Challenge' contestants who have won the most money

Rogan O’Connor is one of The Challenge’s most popular players from the UK. He first appeared on Vendettas, where he was eliminated first, but returned for War of the Worlds 2 and crowned the season’s winner. He also appeared in Season 35 — Total Madness — and placed fifth. Throughout his time on the MTV series, Rogan was the house’s villain. Despite that, his ability to stir the pot while winning competitions made him the champ to root for. In total, he’s won $250,000. 

Wes Bergmann is no newbie when it comes to The Challenge. He’s competed in 14 challenges, from Fresh Meat in 2006 to The Challenge: USA in 2023. So far, the Real World: Austin veteran has won two seasons (The Duel and Rivals II) and has pocketed a smooth $303,000. 

Kaycee Clark is used to cashing large checks since her appearance on Big Brother 20 — where she won by a 5-4 vote. Since then, she’s competed in The Challenge: Total Madness, Double Agents, Ride or Dies, and Spies, Lies, & Allies, which she eventually won. In addition to her $500,000 grand prize from Big Brother, the reality star has taken home $403,000 from her time on The Challenge. 

Just like Kaycee, Amber also competed on Big Brother during Season 16. The CBS alum played alongside former BB players in three separate challenges, one of which (Double Agents) she won. Although she’s only appeared a handful of times, she’s become one of the wealthiest Challenge winners with a whopping $455,000.

Ashley Mitchell is Challenge royalty. She made her MTV debut during Real World: Ex-Plosion and first appeared on The Challenge during Rivals III. Ashley won her second season, Invasion of the Champions, before winning her fourth season, Final Reckoning. Since then, she’s battled it out in five other challenges and made the final during War of the Worlds 2. Over time, she’s collected an impressive $1,121,250. 

There’s no way you can hear about The Challenge and not think of Johnny Bananas. The MTV legend was originally on The Real World: Key West and later appeared on Real World/Road Rules Challenge: The Duel. Since his first challenge in 2006, Bananas has competed in 20 other challenges, with his most recent being in October 2022. He’s won seven seasons throughout his career, bringing his total earnings to $1,222,720. 

Jenny West is another of The Challenge’s international contestants hailing from Wigan, England. The reality star appeared on Survival of the Fittest before starring in War of the Worlds 2 and Total Madness, which she later won. She survived two elimination rounds before winning the $500,000 final challenge.

Cara Maria Sorbello is one of The Challenge veterans who didn’t originally appear on The Real World. The star was drafted by another Challenge vet during her first season — Fresh Meat II. Cara has competed in 14 challenges, made nine finals, and won two. The reality star has earned a total of $602,250. 

Turbo’s reality television debut was during Survivor Turkey 8. The 35-year-old then appeared on The Challenge: War of the Worlds, where he was crowned the season’s winner and earned $750,000. The reality star is passionate, strong, loyal, and such an entertaining watch. 

Although Jordan Wisley has competed in less than 10 challenges, he’s solidified himself as one of the greatest contestants the show has ever seen. Jordan won The Challenge: Battle of the Exes II, Dirty 30, and War of the Worlds 2. Across his seven appearances, the Real World alum has won $871,000. 

Yes, Johnny Bananas is high on the list of Challenge superstars, but if there’s one man who outranks him, it’s Chris “CT” Tamburello. Originally known for his time on The Real World: Paris, CT has competed on 19 seasons of The Challenge — five of which he’s won. CT has earned $1,365,000 from his on MTV and is still counting. 

Darrell Taylor is an original MTV series Road Rules: Campus Crawl cast member. It aired in June 2002 and catalyzed Taylor’s Challenge career ahead. Since his RR appearance, Darrell had an impressive winning record. He snagged the crown during The Gauntlet, The Inferno, The Inferno II, and Fresh Meat, earning him $248,055. 

Yes Duffy was on MTV’s Road Rules: Semester at Sea and the Challenge 2000. He won the latter and appeared shortly after in Battle of the Seasons and Battle of the Sexes. He took a 20-year hiatus before returning to The Challenge: All Stars 1 — where he won the $500,000 grand prize. 

Camilla Nakagawa is one of the Challenge’s most fiery and competitive contestants the show has ever seen. She’s the champion of Spring Break Challenge, Battle of the Exes, and Dirty 30, bringing her total earnings to $561,250. The MTV veteran has been involved in a lot of controversy throughout her run on the show and hasn’t appeared since January 2018. 

Kenny Santucci is Fresh Meat turned a Challenge great. He’s competed in eight seasons and made the final seven of them. He won The Inferno 3, The Island, and The Ruins and has brought in $235,970.