The Top 10 Most Satisfying Wins in MTV Challenge History

CT and Kaycee took home the win on Spies, Lies & Allies after being the two best players all season. While they were deserving winners, the victories didn’t feel especially satisfying because they felt like powerhouses facing no opposition. Not every Challenge’s end-outcome leaves you with a smile on your face, and a good amount of them, you find yourself complaining. Hell, many people weren’t happy with Kaycee winning SLA as she probably wasn’t the best female competitor in the Final. Nonetheless, this article aims to Rank the 10 Challenge Wins that leave/left fans with a satisfied feeling in their stomachs. It is not a ranking of what the most impressive wins are. We are ranking the best storyline finishes, what mattered most for this show’s history, and then a dash of pettiness because sometimes the most satisfying ending is seeing someone you hate lose.

HONORABLE MENTIONS:

Derrick Kosinski (Inferno 3) — Finally getting the win after many heartbreaking losses. Too bad it was part of a six-person team on one of the hardest seasons to find/rewatch. His win gets lost in the shuffle.

Tonya Cooley (Inferno 3) — After Tonya’s terrible performance in the Inferno 2 Final and some of her lower moments on the show, being able to watch her put everything together and be a top competitor for a season was awesome.

Brad Fiorenza (Cutthroat) — He got the win in his 8th season! It would have been more celebrated had it not been Brad’s most lukewarm season as a competitor, and had the Cutthroat Final been more competitive.

Turbo (War of the Worlds 1) — Winning the hardest final ever in your rookie season against a stacked cast should get you on the actual list. So why isn’t it? I can’t answer that, I got to ask the higher-ups.

Jodi Weatherton (Duel 1) & Rachel Robinson (Duel 2) — Strong deserved wins by elite players. Though for some the outcome was a foregone conclusion from Day 1.

Wes (Duel 1) — I loved Wes’s win on the Duel 1, but many would argue CT, Evan, and even Brad were the more impressive players during the season and thus got “robbed” of a victory by Wes.

The Top 10

10 Sarah Greyson — Gauntlet 1

The list kicks off with the original Challenge underdog and the Queen of the Gauntlet, Sarah Greyson. Sarah was the outcast who got voted off the RV during her Road Rules season, then went into 5 eliminations on her Rookie Season (the Gauntlet 1) and came back a winner each time. The fact this is Sarah’s only season, and she set the record for most elimination wins in one season adds to the mystique of it all. It was a magical season for Sarah, and the cherry on top was her getting a Challenge Championship.

9 Team UK — War of the Worlds 2

Watching Paulie, Cara, Ninja, and Zach lose was so much fun. If I could bottle how I felt watching them fail and be able to sell those bottles, I’d be a Billionaire.

I don’t care about Team UK and its members; if anything, most of them are also bad people.

Editor’s Note (Which is also me): This should have been Turbo’s spot on the list.

8 Laurel Stucky — Free Agents

You might see Laurel on this list and immediately think, “I hated how Laurel treated Cara on Free Agents,” or “Laurel is a juggernaut, so her winning wasn’t shocking.” She probably would have been left off entirely if I had written this list three years ago. Except as time passes, I appreciate Laurel winning Free Agents more and more.

Laurel Stucky is simply one of the greatest players ever to touch the Challenge; the way she’s dominated daily challenges and eliminations in a way no other player has is remarkable. On Free Agents specifically, Laurel won 4 eliminations, taking out her two most significant threats in the process (Cara & Theresa). She also won the Final despite Zach Nichols almost costing her the win by dying on a mountain. If Laurel didn’t have a Challenge Championship, the world would not feel right.

7 Ashley Mitchell — Invasion of the Champions

This entry on the list may surprise you. For that reason, it’s why it is on here because Ashley winning Invasion of the Champions was so random, yet it felt incredibly satisfying when you put it all together. Looking back at the cast of Invasion, the female bracket is stacked with Elite competitors (Laurel, Cara, Camila) and strong players who would go on to stake their claim in Challenge history (Ashley, Nicole, Jenna, Kailah, Amanda, Sylvia). Invasion was meant to usher in a new generation of competitors while bringing back some of the best ever to play the game.

On Rivals 3, Ashley proved as a Rookie to be a slightly better competitor than expected. However, nobody would have picked her to win Invasion going in or even during, especially with the cast it had, in a Final going against Camila, who was in the best shape of her life, or Nicole, a fierce physical player and athlete. Instead, Ashley proved brains & heart matter just as much as brawn, killing every puzzle portion and keeping it competitive cardio-wise. It’s vital to note, Ashley played a stellar political game from Day 1 of Invasion; from gathering numbers early to Polidicking Hunter into her corner to being one of the Lavender Lady Alliance founders — she earned her win. The win was random in a good way. Watching Spies, Lies & Allies, where Kaycee & CT were the best players on Day 1 and just ran through the season with close to, if not zero resistance. It makes me appreciate Ashley’s win even more now.

6 Sarah Rice (with Jordan) — Battle of Exes 2

At this point, you will notice a recurring theme of players finally getting their first win during their 8th season. Sarah Rice is one of the best females to ever appear on the Challenge, and she is also arguably the most unlucky player in Challenge history. Throughout the early part of Sarah’s Challenge career, she got dealt lousy partners, bad teams, and terrible circumstances. She literally got sent home twice in a three-season span for her partner DQing/Quitting. Going into Exes 2, Sarah was dead-set on winnings, and the Challenge Gods finally smiled upon her when they gave have her Jordan Wiseley as a partner.

Sarah went on to put up a masterful political game by straddling the Bananas/Wes rivalry perfectly, and in the end, making a cutthroat move to send Bananas against Leroy for the final elimination of the season. Along with Jordan, Sarah won three daily challenges, an elimination, and of course, the Final. It was fantastic to see Sarah finally break through and prove that she was on the level of a Challenge Champion without anything or anyone holding her back anymore. What keeps Sarah from ranking higher is that general fan sentiment towards her is a bit mixed.

5 Cara Maria Sorbello (with Jamie) — Battle of the Bloodlines

It’s sad to say that Cara Maria’s behavior on her last couple of seasons and Social Media in general over the previous few years is aging her Bloodlines Championship like milk. Three years ago, I probably would’ve ranked this as the 2nd most satisfying win, and now, it feels weird to talk about Cara Maria as someone who had a groundswell of love and support.

Nonetheless, it’s impossible to deny that Cara had become the Challenge’s Official Underdog at one point. While Cara had been a stout competitor with three second-place finishes in the past, fans truly fell in love with her on Free Agents after she pulled out three elimination wins, broke her hand, and chose to keep on playing. Seriously, to this day, I believe Cara’s broken hand was the best thing to ever happen to her, as the fans fell directly into the palm of her healthy hand. When she came back for Bloodlines, people viewed her as a Top Contender and the biggest threat to take down an ultimate evil in Johnny Bananas. Cara did just that, taking out Bananas in elimination, winning the Final with her Cousin Jamie, and finally, after 8 seasons, becoming a Champion.

Fan opinion of Cara souring has led people to poke holes in the win, citing its weaker cast and the performance in the Final itself not being spectacular. In the actual season, Cara did receive backlash due to the entire mess of her relationship with Abram. Still, I’d be lying if I said I wasn’t cheering my ass off for Cara during Bloodlines.

4 Chris Tamburello — Invasion of the Champions

CT winning Invasion his first season after becoming a father and his first season back after Diem’s passing (RIP Legend) is a guaranteed lock on this list. Do I need to explain this more?

3 Landon Lueck & Carley Johnson — Fresh Meat 2

On Fresh Meat 2, Laurel & Kenny came together to create potentially the strongest co-ed pair in Challenge history. They worked together with such great synchronicity, and Laurel was simply on another level as an athlete. You replay that season 100 times, and they probably win 99 times. Except we live in the 1 out of 100 scenario where Landon & Carley overcame the Goliaths that were Laurel & Kenny.

After Landon got stuck with the last pick of FM2, he expected him and Carley to have an early exit (in an interview years ago, he revealed that he called home telling his family to assume he’d be back in a week or two). As they competed in the challenges together, Landon realized that while Carley might not be the best athlete, she was mentally tough and that he would put in more than 110% to fill in all the gaps for them to succeed. The season was an uphill battle for them, and the Final itself was a literal climb up a mountain in which Landon dug his head into Carley’s ass for them to edge out the win barely. Landon was an absolute superhero during this season and Final, and it was a win he got back after a crushing late-season loss on the Duel 2. Meanwhile, Carley went from the last overall pick to Challenge Champion! That’s a hell of a story and an ending.

2 Paula Meronek (with Evelyn Smith) — Rivals 1

When I interview old Challenge cast members, multiple players note that back in the day, people in the house didn’t talk too much about their stats when it comes to championships and finals. As the show progressed and became a more serious competition, the people who hadn’t won had this monkey on their back they needed to get off. Derrick and Brad were two male players who dealt with this, and when they got their wins in Team Formats, it didn’t hit the same way as our #2 entry, Paula.

When Paula showed up for Rivals 1, she was going into her 8th season, which holds a bit more power than Cara & Sarah because, at that point in time, no female in Challenge history had done more than 8 seasons. Paula was coming on this show, knowing everyone was either rooting for her to win or were hating on her, hoping she’d continue to lose. Up until Rivals 1, Paula would not only lose; she would do so in disastrous fashion: Big Easy dying in the Gauntlet 3 Final, her friends Kenny and Johnny leaving her off the boat on the Island, taken out by her nemeses Aneesa & Evelyn on the Duel 2 & Fresh Meat 2, and betrayed by Dunbar as she got thrown into the final elimination of Cutthroat. Paula’s story differed from the Brad-Derrick-Sarah’s in that she wasn’t an outwardly phenomenal competitor. She was a flawed player who commonly made missteps politically and often put trust in the wrong people. Paula was never an elite athlete; she was a solid swimmer with phenomenal cardio after years of training; she just wasn’t a Laurel or a Jodi.

There was also an element of anyone who watched Paula from Day 1 of her Real World Season went on a journey with her. We watched her have a severe battle with Anorexia. Nobody watching Real World Key West would have expected Paula to be at the top of a mountain after the most extreme Challenge final (at the time), looking like an absolute beast. Paula’s win was an emotional moment, and from an editing perspective, was something producers would look to replicate in future seasons. If I could change one thing about the win, it would be dyeing her hair back to her patented Blonde-look as Paula finally getting the win during the one season she was a brunette felt a little off.

1 CT & Wes Rivals 2

A win that encapsulates a special time and era in Challenge history.

CT and Wes were already viewed as Challenge Legends going into Rivals 2. The two of them individually became legends through their willingness to take on an entire house by themselves with zero regards for feelings. Watching CT take on an entire house in Rivals 1 with everyone plotting against him let you know how powerful he was. Wes going into elimination after elimination on Fresh Meat and the Ruins and coming back had you in awe. And yet, what made CT and Wes Legends, led to them not having as much success when it came to winning Challenge Championships, as their gameplay style always had them fighting uphill battles. Or, simply, their egos and temper got in the way. After 8 seasons, CT was still winless. While Wes had won the Duel 1, he’d lost five consecutive seasons and was at a low point after being an early exit on both Exes 1 and Battle of the Seasons. Rivals 2 was a serious breaking point for both men in their Challenge careers, so their partnership came at the perfect time.

Hilariously, CT and Wes were pretty underwhelming for the early part of Rivals 2, mostly coasting on name value, veteran status, and CT’s Polidicking. They got themselves in better shape and formed a genuine camaraderie as the season went on. CT and Wes won the final two daily challenges dominantly with an absolute swagger. In the Actual Final, they ran rough-shot through the competition, winning the opening puzzle-purge on Day 1 by a massive margin and quite literally holding the lead against Bananas and Frank during Day 2 for its entire duration. Watching CT finally become a Challenge Champion felt right, and Wes overcoming his embarrassing losses to be back on top was needed. The fact they beat such a dislikable pair in Bananas and Frank in the Final made it all the better, to which it must get repeated; they demolished the two reigning champs in the Final.

To this day, CT is the only player to become a Challenge Champion for the first time after their 8th season, and Wes has the longest gap between wins on the main franchise (7 years between the Duel 1 and Rivals 2). Something great about this pairing was it felt like they inflated each other’s egos and then actually performed to the level of those egos. CT and Wes knew if they wanted to stick their tongue out and shrug like Michael Jordan, they had to be as clutch as him, which led to a brilliant performance by them.

--

--

--

25 years old. I blog about MTV's the Challenge and will dabble into other subjects occasionally. Follow me on Twitter for the occasional bad joke.

Love podcasts or audiobooks? Learn on the go with our new app.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Allan Aguirre

Allan Aguirre

25 years old. I blog about MTV's the Challenge and will dabble into other subjects occasionally. Follow me on Twitter for the occasional bad joke.

More from Medium

Top 10 Weakest Casts in MTV Challenge History

Every Season of The Challenge Ranked: #39 —  Battle of the Sexes 2

The Nelson Streak (Continued): 0–51 — Real or Unlucky?

Raise Your Glass To The Rotten Banana Podcast