For more than 25 years, MTV’s The Challenge has crowned some of reality television’s greatest competitors. While dozens of players have won at least one flagship season, only a select few have captured multiple championships.
Here’s every multi-time flagship champion, ranked by the number of wins, followed by every one-time champion as of July 2026.
Seven-Time Champion
Johnny Bananas — 7 Wins
No one has won more flagship seasons than Johnny Bananas. His victories span multiple eras of the game, cementing him as one of the greatest competitors in Challenge history. (Yahoo)
Five-Time Champions
CT Tamburello — 5 Wins
CT evolved from one of the show’s most intimidating competitors into one of its most complete champions, dominating both physically and mentally. (Yahoo)
Jordan Wiseley — 5 Wins
Jordan became just the third player in flagship history to reach five championships after his victory on Battle of the Eras. (TV Insider)
Four-Time Champion
Darrell Taylor — 4 Wins
Darrell’s first four appearances resulted in four championships, one of the most remarkable starts to any career in franchise history. (The Challenge)
Three-Time Champions
Veronica Portillo Rachel Robinson Evelyn Smith Wes Bergmann Landon Lueck
Each of these competitors owns three flagship championships and helped define different eras of the franchise. (The Challenge)
Two-Time Champions
Ashley Mitchell Cara Maria Sorbello Laurel Stucky Sarah Rice Jenny West Emily Schromm Jodi Weatherton Jamie Murray Jamie Chung Susie Meister Rogan O’Connor Devin Walker Kaz Crossley* Kaycee Clark Tori Deal Amber Borzotra Turbo Çamkıran MJ Garrett Alton Williams Theo Von Mark Long Colin Mortensen
*Kaz Crossley has one flagship win and additional championships outside the flagship series. (The Challenge)
One-Time Champions
The following competitors have each won one flagship season:
Abram Boise Olivia Kaiser Adam Larson Aviv Melmed Brad Fiorenza Camila Nakagawa Carly Johnson Carley Johnson Chris Underwood Derrick Kosinski Emanuel Neagu Frank Roessler Frank Sweeney Holly Shand Hunter Barfield Ibis Nieves Jillian Zoboroski Kina Dean Nehemiah Clark Paula Meronek Roni Martin Sam McGinn Svetlana Shusterman Timmy Beggy Tyler Duckworth Yes Duffy Aviv Melmed Kelley Limp Coral Smith Dan Setzler Julie Stoffer Syrus Yarbrough Sean Duffy Elka Walker Mike Mizanin Rebecca Lord Kameelah Phillips Dave Giuntoli Christena Pyle Kendal Sheppard Katie Doyle Randy Barry Mike Lambert MJ Garrett Randy Barry and dozens of additional early-era team champions from Seasons 1–11, when entire teams won together. (The Challenge)
Final Thoughts
Winning one season of The Challenge is an incredible accomplishment, but winning multiple flagship championships is what separates the legends from everyone else. Johnny Bananas still leads the way with seven titles, while CT Tamburello and Jordan Wiseley continue to chase history with five championships each.
With every new season, the leaderboard continues to evolve, but these competitors have already secured their place among the greatest champions the franchise has ever seen.
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