CT Tamburello on The Challenge
(Photo credit: MTV's The Challenge/YouTube)

The Challenge Winners Who Have Won the Most Money

On The Challenge, there have been many winners over the years, but not all of them rank as the richest Challenge winners. MTV’s The Challenge has been a staple on the network since 1998. On the show, participants from past seasons of Real World and Road Rules were placed against one another and divided into two separate teams to see who would come out victorious. As the game morphed over the years, pairs of friends, lovers/exes, or family entered an arena at an unmarked destination, hoping to become victors of the spoils. 

There, each team battled it out in a test of grueling physical obstacles and mental puzzles. Each game conquered led the teams closer to a one million dollar cash prize. With popular host, TJ Lavin, always providing quality one-liners, the series has grown to become a cult favorite. But who has won the most money?

Tori Deal ($454,000)

Tori Deal/Instagram

Tori Deal made her way to The Challenge by the way of Are You The One? Even though she didn’t find the love of her life, she did find her love for competing, and a gladiator was born. For years, Tori has dominated the women’s group thanks to her strength and will to survive.

This year, on Ride or Dies, Tori and her partner, Devin Walker, won the one million dollar prize. However, instead of choosing to become a part of the millionaire’s club, Tori shared her winnings with the losers. Both Tori and Devin revealed they would be gifting $38,000 to each of the six finalists who failed to cross the finish line first. This generous move puts Tori at the bottom of the list when it comes to richest Challenge winners, though she still took home $454,000. 

Jenny West ($500,000)

Jenny West/Instagram

Jenny West has always been an athlete and prides herself on being an online transformation coach. Along with her twin sister, Lucy, the two have made a name for themselves within the fitness world. During her time on the series, Jenny competed in War of the Worlds 2 and won Total Madness. While she has been MIA for the last three seasons, she still has won a decent prize pot of $500,000. 

Jenny has yet to comment on why she won’t return to The Challenge, but it could be that she is just too strong for the competition, often blasting other competitors right out of the ring. It also didn’t help that Jenny was genuinely a nice person who made for boring TV. 

Yes Duffy ($511,254)

Yes Duffy/Instagram

Yes Duffy was first seen on Road Rules: Semester at Sea back in 1999. After his short stint on reality TV, Yes took an almost two-decade break until returning to the MTV game show. Yes, then went on to win Challenge 2000, where he took home $11,254 and The Challenge: All-Stars 1, where he took home $500,000.

Now, Yes works as an artist and activist. Yes, not only one the money, but he won the hearts of fans for his truly motivating story. 

Camila Nakagawa ($561,250)

Camila on The Challenge
MTV’s The Challenge/YouTube

The spitfire from Brazil made her first MTV appearance on Spring Break Challenge and was the only interesting cast member to make an impact on ratings. Overall, Camila Nakagawa has competed in ten seasons of The Challenge, which makes her one of the top veterans and richest Challenge winners. She won money on three seasons—Battle of the Exes, Invasion, and Dirty 30—for a combined winnings of $561, 250, via Medium.

Camila’s love for drama and midnight make-out sessions always made for interesting TV. Sadly, Camila’s famous temper tantrums were a bit too much for the cast and crew to deal with. She was subsequently banned from any future competitions after punching a PA. 

Cara Maria Sorbello  ($602,250)

Cara Maria Sorbello/Instagram

Cara Maria Sorbello was first looked at as a weak competitor. However, over the years, she has taken the time to work out and invest in her health, returning as a champion. The Challenge champ first debuted on Fresh Meat when she dated Abram Boise. Cara was a consistent underdog, which made her popular with fans, but once she started winning, she just couldn’t be stopped. 

On The Challenge, Cara Maria won money on several seasons, including Cutthroat, Rivals, Rivals 2, Battle of the Bloodlines, and Dirty 30, though her biggest payout was on Vendettas, where she took home $378,750. Combined, Cara Maria’s winnings total $602,250.

Turabi “Turbo” Camkiran  ($750,000)

Turbo Camkiran/Instagram

Turbo Camkiran took the game to heart, which was what made him great and awful at the same time. The Turkish competitor got his big win in War of the Worlds after knocking some heavy hitters from the winner’s ring. He ended up taking home $750,000 for that win.

Sadly during War of the Worlds 2, Turbo tried to reclaim his crown but instead left the season early for threatening Jordan Wiseley and the show’s security. 

Jordan Wiseley ($833,000)

Jordan Wiseley/Instagram

Jordan is undoubtedly a Challenge champion, though his attitude needed adjusting at times. Extremely athletic, Jordan regularly dominated the competition, and he ended up winning three of the five finals he made it to.

For his wins on Battle of the Exes 2, Dirty 30, War of the Worlds 2, and coming in third on Rivals 2, Jordan has racked up $833,000 worth of wins, making him one of the richest Challenge winners.

Ashley Mitchell ($1,121,250)

Ashley Mitchell/Instagram

The unbeatable Ashley Mitchell is one heck of a millionaire. The veteran has gone on to win two finals, Final Reckoning and the Invasion of the Champions. Just like Johnny Bananas on a previous season, Ashley decided to keep the entire one million dollar cash prize on Final Reckoning, leaving partner Hunter Barfield with nothing. 

Added up, Ashley’s prize money take home comes out to $1,121,250, which is why she gets to call herself Ashley “Millionaire” Mitchell.

Johnny Devenanzio ($1,222,720)

Johnny Bananas/Instagram

The villain of the MTV series, Johnny Bananas, has made quite a name for himself. Johnny is another member of the Real World cast who found fame by accepting challenge after challenge. There is no doubt he is one of the strongest competitors and has proven this theory time and time again, appearing in 21 seasons. Johnny may be best known for keeping the full cash prize leaving his partner, Sarah Rice, in tears.

Johnny has so far won a whopping seven seasons, and it doesn’t seem like he’s done just yet. With his first place wins on The Island, The Ruins, Rivals, Battle of the Exes, Free Agents, Rivals 3, and Total Madness, along with his other prize money from The Inferno 3, Rivals 2, and Ride or Dies, Johnny has taken home $1,222,720.

Chris Tamburello ($1,364,750)

CT Tamburello on The Challenge
MTV’s The Challenge/YouTube

Without question, the GOAT has to be CT Tamburello; the muscle, the fighter, and the stud. From his fist fights to his on-screen relationship with Diem Brown, CT was always a fan favorite. Like any great competitor, he is still feared in the elimination round. CT has competed in fewer challenges than Johnny but has still done well for himself, leaving viewers to wonder if he will return for another try at the cash prize.

The Boston native won back-to-back seasons recently with Double Agents and Spies, Lies, & Allies, along with his wins on Rivals 2, Invasion of the Champions, and War of the Worlds 2.  In addition to the money he earned on other seasons (not as a first-place winner), CT has won a whopping $1,364,750, making him the richest Challenge winner.