On episode 14 of Battle of the Eras, Cory knew he was facing the Arena. This is a familiar setting for the multi-season finalist, and he worried that if he lost, he’d be known as the best Challenger to never win.
And if we’re being fair, he might have the title — but who else is a contender? While there are many factors when naming the “best Challenger to never win,” I’m going to look at some objective metrics to determine who deserves the title. Specifically, we’re looking at the number of final appearances and number of elimination wins.
I am only looking at people who have done 3 Challenges or more and have made the final over 33% of the time. I omitted Champs spinoffs, but I did include All Stars, the USA series, and the World Championship. Also, I didn’t factor in daily challenge wins because they often aren’t required to be successful in the game. Cory actually has the longest winning streak, but it’s from Bloodlines, and the Blue Team threw every challenge that season.
Honorable Mentions
Ruthie Alcaide
Challenge Appearances: 5 (4 main series + All Stars 1)
Final appearances: 5 (40%)
Elimination wins: 1 out of 3 (33%)
Ruthie has always thrived as an underdog. This got her to the final on Battle of the Sexes, her first season, and All Stars 1, her most recent appearance. While her number of elimination wins may be low, it’s important to note that her first two seasons didn’t have eliminations, and she was a very fierce competitor then.
Paulie Calafiore
Challenge Appearances: 5 (4 main series + USA 2)
Final appearances: 2 (40%)
Elimination wins: 2 out of 5 (40%)
Paulie came onto The Challenge with a really hot temper, but that may have been the fuel to his success. He got to the end of Final Reckoning and War of the Worlds 2 — then he “took” a long break from the show. While the new version of Paulie is much calmer, he’s also struggled to regain the success he had on his earlier seasons.
Nany Gonzalez
Challenge Appearances: 12
Final appearances: 4 (33%)
Elimination wins: 7 out of 17 (41%)
When Nany debuted on Battle of the Season, fans got familiar with a fiesty but formidable competitor. She did well during her early seasons, but she took a multi-season break after Rivals 3. Upon her return, she found herself with a new group of people. She joined the Vacation Alliance, which calmed her down and helped her earn three consecutive finals on her most recent appearances — but none of them resulted in a win.
10. Kellyanne Judd
Challenge appearances: 8 (5 main series, 2 All Stars + World Championship)
Final appearances: 3 (38%)
Elimination wins: 6 out of 12 (50%)†
Kellyanne is known as an emotional player, but one who can persevere and impress. She started off her time on the Challenge by defeating Rachel in an Island face-off, and she almost made the final that season, but her key was stolen. Then, she made the final on The Ruins before taking a long hiatus. In more recent years, she preformed well on All Stars, to the point where she probably would have won All Stars 1 if the season crowned a male and female winner.
9. Kyle Christie
Challenge appearances: 7
Final appearances: 3 (43%)
Elimination wins: 7 out of 13 (54%)
Kyle’s run on the Challenge has been quite successful, despite having the odds stacked against him. He made the final on his first season, even though he was a UK competitor invading the US series. Then, he established rivalries, but this helped him learn to navigate the game. His later seasons have brought him closer to victory, and last time we saw him he was seconds away from winning Spies, Lies and Allies.
8. Jenna Compono
Challenge Appearances: 8
Final appearances: 3 (38%)
Elimination wins: 6 out of 10 (60%)‡
Jenna made the final on her first season, but she would have been branded as the ultimate lay-up if she didn’t make the final on her next two seasons: Bloodlines and Rivals 3. In the process, she won multiple eliminations and rebranded as the “Barbie Beast.” Though her earlier seasons were more successful than her later ones, she has a lot of potential to return to a final — and even win — if she makes a comeback.
7. Theo Campbell
Challenge Appearances: 4 (3 main series + World Championship
Final appearances: 2 (50%)
Elimination wins: 5 out of 7 (71%)
Early into his Challenge career, Theo was hot-headed, arrogant, and a serious threat. He was close to winning the grueling War of the Worlds final, and he won multiple eliminations on War of the Worlds 2. Sadly, an eye injury halted his Challenge career, but when he returned on the World Championship years later he also returned to the final… where an injury caused him to tap out.
6. Jenn Grijalva
Challenge Appearances: 6
Final appearances: 4 (67%)
Elimination wins: 5 out of 8 (63%)†
For a while, it seemed like Jenn was the ultimate runner-up. She debut onto The Challenge with an impressive run on The Inferno 3, but when she learned to play a more aggressive game, she discovered she wouldn’t need to risk elimination if she had friends protecting her. This helped her make four finals, but she always came in last and only took home money after her appearance on Cutthroat.
5. Faysal Shafaat
Challenge Appearances: 5 (4 main series + USA 2)
Final appearances: 3 (60%)
Elimination wins: 6 out of 7 (86%)
Faysal gets a bad rap, particularly for his run on Double Agents. That season, he refused to compete in the eating portion of the final, but he knew that he wouldn’t advance in the game due to his partner Kaycee’s knee injury. His other seasons were more impressive. On the USA 2 final, he pushed through his biggest weaknesses (like eating and math) and had a serious shot at winning until an ax throw ruined his chances.
4. Kam Williams
Challenge Appearances: 6 (5 main series + All Stars 4)
Final appearances: 3 (50%)
Elimination wins: 9 out of 12 (75%)
The nickname Killa Kam exists for a reason. Kam has sent many people home in eliminations (even more if you look at redemption games), and she’s fought her way to multiple finals. You could call her a “robbed goddess” after her Vendettas departure, but the nickname Queen Kam is only self-given because she’s never left a Challenge season with a first place victory.
3. Leroy Garrett
Challenge Appearances: 14 (13 main series + All Stars 4)
Final appearances: 6 (43%)
Elimination wins: 10 out of 16 (63%)
Much like Kam, Leroy made the final on his first season of The Challenge. He saw various levels of success on later seasons, but it felt like he got much more serious about the game when he met Kam. This led him to be a team leader on War of the Worlds 2, where he ran the final until he got purged. After a record-breaking six finals, he still doesn’t have the win, but he continues to fight for another shot at victory.
2. Nicole Zanatta
Challenge Appearances: 4 (3 main series + All Stars 4)
Final appearances: 3 (75% — only missed final due to a medical DQ on Double Agents)
Elimination wins: 2 out of 2 (100%)
While Nicole has a questionable reputation off of The Challenge, she has a super strong record on the show. She’s never lost an elimination, and the only time she didn’t make the final it was because she dislocated her shoulder on Double Agents. Nicole makes navigating the game look easy, but she has weaknesses that tend to show up in the final. If she encounters trivia, math, or puzzles, she’s basically dead on arrival. Perhaps that’s why she always finished in the lower-half of the finals she’s appeared in.
1. Cory Wharton
Challenge Appearances: 11 (10 main series + USA 2)
Final appearances: 5 (50%)*
Elimination wins: 11 out of 15 (69%)‡^
Since his debut on The Challenge, Cory has been making moves in the game. He’s proven to be a serious threat for the veterans, and he’s been responsible for getting Challenge legends sent home. And unlike other people on this list, he doesn’t always come in dead last in his final appearances. He was seriously close to winning Total Madness, and he’s continued to put up impressive performances, including his run on USA 2.
*only looks at data up to Season 40 episode 16
^Final Reckoning elimination counts as 2 wins since Zach & Amanda and Jose & Da’Vonne were defeated
† Winning or losing the daily challenge on The Island is factored
‡ Includes full Underdog Purge on Invasion of the Champions
Stop Being Polite 
Jenna would be my vote.