Sarah winning Exes 2 and CT winning Rivals 2 are all examples of great challenge season that had gratifying endings to them. This list is going to be the seasons where players excelled, but eventually came up short in DRAMATIC or unexpected fashion.
10 Theresa Gonzalez — Free Agents
If you look at Theresa’s Challenge stats, she really does not seem like a great competitor on paper. She was a career 2–6 in eliminations, only made one final, and technically got eliminated from every season she appeared on. However, if you watched the show, especially in Theresa’s final two seasons, you saw an elite competitor who had all the skills to become a multi-time champion. Theresa is tall with long legs, an elite swimmer, has incredible cardio, great speed, held great technical skill as an athlete, and a memory better than Sarah Rice.
Why did Theresa fail so epicly in her first four seasons? It’s a mix of bad partners, bad luck, and her inability to compete when nervous. However, once she was able to compete as an individual on Free Agents, Theresa began to actively play the game, do well in challenges, and made it to the final four. Despite being inferior to Laurel as an overall competitor, the final was Theresa’s opportunity to shine as she is a much better runner than Laurel. However, a last minute elimination twist forced Theresa to face Laurel in a three tiered puzzle where Laurel ultimately came out on top.
Had the game played out normally, either Nany or Devyn would have been the final player eliminated and Theresa would have had a good shot at winning. Nany was not too far behind Laurel in the final, and even though Nany is a nicer human than Theresa, Theresa is better than Nany at most competitive aspects of the Challenge.
9 Paulie Calafiore — War of the Worlds
Last season, Paulie wrecked the game alongside girlfriend Cara Maria. While they had friendships in the house, they were generally an alliance of two. They were able to sustain themselves by dominating the daily challenges. Paulie found himself on the winning side of 7 out of 13 daily challenge. 3 as a pair with Ninja, and 4 times as an individual. He proved he was good with cardio, puzzles, speed, swimming, and everything in-between. With the final in the grasp of his hands, Paulie choked.
Due to the way Cara and Paulie present their relationship, they create more enemies than fans. It’s easy to root against them, but watching Paulie continually falls into the water hurt like hell. As a human being, you could tell making the final together was their goal and now it’s not happening. The good thing is, it humbled Paulie and now they have an incredibly secure and not problematic relationship…
8 Brad Fiorenza — Battle of the Sexes 2
On Battle of the Sexes 2, the game was simple. If you kill the daily challenges you will remain safe and they will not vote you off. Brad dominated. He outlasted the Miz, Abram, Derrick, Shane, and Frank Roessler in order to make it to the final five. Unfortunately, the alliance of Mark, Eric, Theo, and Den decided it was time for Brad to go home and they voted him off.
It was a bit sad as there were no eliminations where Brad could prove himself. In a season where his merit got him to the end, he got his throat cut for essentially being a good and loyal soldier. What an era.
7 Coral and Evan — Fresh Meat 1
Of the first six competitions from Fresh Meat 1, Evan and Coral won five of them. The one they did not win was a lifesaver challenge that they threw in order to give the other teams a win and so they would come off as less of a threat.
Unfortunately, Evan sustained a hernia while on the show. He did not leave the show despite the severity of the injury. However, he and Coral became a more average team overall. It was actually Coral’s knee dislocation which led to their disqualification. Considering Evan had internal bleeding, it is a godsend Coral’s knee popped out. Evan and Coral are the biggest what if team of all-time; they were so much better than their fellow competitors. Not to mention the fact the final was originally supposed to have four teams instead of three. which affected the final outcome massively. This Challenge hurts my heart especially knowing Coral’s only other appearance was the Gauntlet 3.
6 Shane Landrum — Invasion of the Champions
Shane’s ascent on Invasion of the Champions was actually a bit of a slow build that turned into something huge. Originally, Shane was simply attempting to assimilate himself into a younger cast, having not been on the show for a literal decade. He won the final daily challenge to secure himself a spot in the Oasis and then took off running.
In a somewhat upset, Shane demolished Tony in elimination and then was able to control the game/team. Shane secured half the female underdog votes in the Oasis with Ashley, Amanda, and Sylvia. He created a side-deal with Nicole to ensure mutual-safety. And overall, he was the most vital player to the Underdog team. During the hamster wheel challenge where most of his team failed, Shane succeeded with ease despite his fear of heights. In the curry eating challenge, he ate his teammates bowl because they were not able to stomach it (despite having a long history of vomiting). He came up with the strategy of kamikazi-ing the other team during the “Fall Out” daily challenge. Shane played politics and competitive side at such a high level, and he likely would have won the final considering it involved swimming, eating, cardio, and puzzles.
Instead, the Underdog bloodbath cut him off at the knees. Shane’s biggest Challenge weakness will always be raw physical eliminations. He is a strong male who can lift his own body weight and then some, but Shane has no instincts or aggressiveness when it comes to 1 on 1 contact. It sucked watching Shane lose to Cory when Cory is only better than him at 1 facet of the game.
5 Tony Raines — Vendettas
Tony on Vendettas showed great character growth. Through his first four seasons, Tony had been a flat out failure. He cheated on his girlfriend(s) multiple times on live television, he had been sent home for physically cornering a female, he fought his brother, had lost multiple eliminations in embarrassing fashion, and the biggest win of his career (the one against Darrell) was called a fluke. When Tony came on Vendettas, he was a new competitor.
Tony was swimming, eating like Kobiyashi, and even traversing heights challenges despite having the balance of a baby deer. His biggest moment of the season was when he came out of Bananas’ shadow and voted him into elimination, thus resulting in his elimination. Tony Time became an actual thing. I went from a Tony hater to a Tony lover. He became the man. Sadly, his appearance in the final was abysmal. Tony finished fourth place out of the four places and didn’t even complete day one. To this day, that’s his only final performance in six regular season appearances. At least he separated himself from Bananas and never went back into his shadow.
4 Landon Lueck — The Duel 2
Landon has an interesting case on this list. I think in the moment, Brad’s upset win over him was underrated because Landon himself was a bit of a boring personality and we didn’t have the retrospective view of Landon’s career.
Knowing what we know now about Landon’s Challenge career, his loss on the Duel 2 is incredibly devastating. Landon was on four seasons, he made the final on three of them, and he won them all. His one loss came on the final elimination of the Duel 2 where the men pulled a fast one on Landon by agreeing to vote him in behind his back. Landon’s loss to Brad hurt as the final ended up being a crossfit exhibition with a long distance bike ride. If you didn’t know, Landon rode a bike for a living at one point. It hurts even more as Landon won 5/9 daily challenges in that season. Brad didn’t win a single daily challenge by comparison. Yet, all that mattered was their one elimination where an ingenious move resulted in the only blemish in Landon’s Challenge record. Landon’s performance on Fresh Meat 2 heals the wound a bit.
3 Derrick Kosinski — Gauntlet 2
Originally, this was number one on my list. Any of the top three can really go in any order in my opinion. I’ve switched them around multiple times. Captain Derrick is remembered as the king of the gauntlet. He went into the Gauntlet four times and came back four times. Derrick eliminated Challenge Champions Adam Larsen and Syrus Yarbrough, future Champion Brad Fiorenza, and nice guy Ace Amerson.
In a format built against him, Derrick kept fighting and fighting. When his team lost the final daily challenge and he was forced to face Timmy in elimination, you could see Derrick was visibly frustrated by the game. Even TJ respected Derrick as he let him spin the wheel to decide what game they would play. The worst outcome followed, Derrick got “Reverse Tug of War”, a game where size is all that matters. At least in regular tug of war, grip strength and upper body can change the equation. Derrick had no chance against Timmy. Even sadder as Timmy’s desire to win wasn’t super high.
2 Wes Bergmann — Exes 2
Wes is a bit overrated as a politician in terms of the history on the show. He’s often had too many blunders to be the master of politics. However, Wes Bergmann played the most beautiful political game in Challenge history on Exes 2.
When Wes won the first daily challenge of the season, he made a deal with the rookies that he was not going to vote in a rookie team for guaranteed safety from them. On day one, Wes assured that 4 out of the 14 teams in the game were not going to say his team’s name. While these are not strong teams, it meant Wes had less enemies. He also voted in Dustin and Jessica, a team which would likely either lose or not be able to come back to bite him. Wes also made a deal with Sarah, being each other’s #1 or 2. This eliminates half the board from targeting him and allows him to float around socially, levy his power, and create even more alliances as he had an entire half of the house assume they were safe with Wes. His decision to not pull the plug on throwing Bananas into the first elimination saves him when Bananas wins the next episode. A few weeks later when he does win, Wes goes for the jugular. He votes in Bananas, and aligns with Zach/Jonna.
Wes’ new #1 is a strong ally, who is still a weak team to face in the final. His #1 is also in a showmance with Jenna, and that’s perfect because he still has the day 1 alliance with Jay that has turned into a safety vest. Wes now focuses on keeping Jay and Jenna around as they are a lay-up. Not to mention, they somehow win a daily challenge and end up throwing Leroy in to face Johnny Reilly and Averey, thus doing Wes’ dirty work for him. As an aside, Wes has created a tight bond with the upstairs residents of the house, including Averey and Nia. So even though Nia and Averey’s male partners were aligned with Bananas, they personally were closer to Wes. It led to internal strife with Reilly and Averey, and ultimately helped Wes’ biggest move which was convincing Leroy to throw in Zach and Jonna into elimination instead of him. Leroy held the gun to Wes’ head, and then gave him the gun.
Then the exile twist fucked up the game. Wes and Leroy were against Jordan and Jay was floater going into the final four daily challenge. A returning Bananas joined Jordan, and Leroy went back to his best friend. Wes was now alone because of an unprecedented twist. The first daily challenge was a game where teams could team up against one another, so Wes and Theresa had no chance of winning. Their elimination was Hall Brawl, where a very skinny Wes likely weighed closer to Nia than Leroy. So close yet so far.
1 Cara Maria — Free Agents
While Cara Maria has become the female face of the franchise, she was very much a supporting player throughout her first five and a half seasons on the show. She was the person who would show up on the cast list and make people go “why are they casting her?” Originally, the main reason was availability.
During Exes 1, MTV wanted to pair Abram with Coral. Coral chose not to do it, so they paired him with current girlfriend Cara. On Battle of the Seasons, Carley was supposed to be on Team Fresh Meat. If you notice, Cara Maria’s jersey is a “Carley” jersey that has tape covering the “ley” portion with her own name. And on Rivals 2, she was an alternate (originally Ayiiia was her partner if they needed a new team) and was partnered with Cooke, a person who she had never met. As they say, the best ability is availability, and Cara was that. Fans finally began warming up to her on Rivals 2 as her and Cooke made an incredible ragtag underdog duo who fought their way tooth and nail to the final and almost took down the behemoth of Emily and Paula. There was still a heavy amount of doubt in Cara as a competitor as she had made her three finals alongside Laurel twice and Cooke once, both physically imposing females.
Once Cara was put in the spotlight as a stand-alone competitor, she showed out on Free Agents. In one of the most intense Challenge eliminations of all-time, Cara took out the near 6 foot Nia. What’s crazy about this elimination is production literally changed it because the original version the two girls played in was far too unsafe. The harnesses were far too tight, and they had to drag the other player an incredible distance in the sand. If you notice, they have a rope when they do it again later in the season. This is how Jordan was able to defeat Swift so swiftly. He was able to get to the rope first and pulled himself in easily. Cara and Nia had to rope to pull themselves in with. She then went on to eliminate LaToya and perform impressively in every individual portion. Cara killed the rope climbing challenge, she finished second to Laurel in the human sandwich challenge, and in the Dug Out challenge only lost because of Jessica.
What made Cara even more of a badass is she was doing this while fighting with her best friend Laurel. Cara had long lived in Laurel’s tall shadow. Now she was killing it in the challenges and was able to prove she was a varsity player. Then Cara’s elimination with Jessica happened. Cara won in Balls In 2–0, but she broke her hand in the process. She chose to remain in the game and ended up facing Laurel in Wrecking Wall, an elimination where you likely need two hands to punch a wall.
Part of the reason I put this at number #1 is because this is the version of Cara Maria that a lot of her current and former fans fell in love with. When you talk to most Challenge fans, a good amount of the people who currently hate Cara, actually loved her at some point. Free Agents Cara Maria was the biggest underdog who fans could all get behind. We had literally watched her grow as a competitor throughout the years and finally become a champion level competitor. Her loss tugged many heartstrings. To this day, fans want Free Agent Cara back as she was the best of both worlds.