CT’s 10 Biggest Moments on ‘The Challenge,’ Ranked

The debate over who the greatest all-time competitor on The Challenge will forever have different answers, but one name who will surely always be up there in contention is CT Tamburello. With nearly two dozen seasons under his belt, CT has had one of the most incredible journeys in the history of the entire franchise. From kicked off for fighting to fighting for the win. From being a quintessential bad guy to softening up and winning the heart of an amazing woman, CT’s transformation on The Challenge is one of the most incredible in the entire series. He may claim he’s retiring season after season, but he just simply can’t say no.

Rising to prominence first on The Real World: Paris, CT Tamburello made the quick and logical jump over to The Challenge, known as Real World/Road Rules Challenge back in his day. The Massachusetts brought his bad boy reputation that followed him for a large part of his early career on The Challenge. Between playing on the Bad Guys team to tossing a few punches that got him tossed out, CT kept up his persona. But as he started to change, thanks to the love of a special person, CT’s head got focused on the game, allowing him to net multiple final appearances and season victories. Within the flagship series, he has appeared on twenty seasons, as well as Champs vs Pros and Season 1 and Season 2 of Champs vs Stars, in which he was victorious both times.

He was a finalist for The Inferno, The Inferno II, The Gauntlet III, Battle of the Exes, and Dirty 30. But he got the honor of challenge champ, with victories in Rivals II, Invasion of the Champions, War of the Worlds 2, Double Agents, and Spies, Lies & Allies. Solely in his career on The Challenge, he has netted approximately $1,375,000. Plus, he was the winner of the second season of The Traitors, along with The Challenge alum Trishelle Cantanella. With a storied career and long resume, CT has certainly had some incredible moments. But here are some of the best of the best!

10 CT Starts His Career

‘Real World/Road Rules: The Inferno’

Everyone’s got to start somewhere. For CT Tamburello, his journey on The Challenge, as it would soon be known, began in 2004. A year following his appearance on The Real World: Paris, CT was part of Team Real World on Real World/Road Rules Challenge: The Inferno. Hosted by Dave Mirra, the eighth season of the program featured 20 all-star alums of the titular programs as they hit the beaches of Acapulco, Mexico. Alongside three of his Paris roommates, Ace Amerson, Leah Gillingwater, and Mallory Snyder, CT had a strong first-season showing. He proved he was a formidable competitor, and he would be an asset to the show.

He took a season off before returning for Real World/Road Rules: The Inferno II, a season that would set him up and establish his reputation. While still using the Real World/Road Rules Challenge title, the cast was not split from their original program. Oh no, it was Bad Asses versus Good Guys. Of course, CT and his hot-headed history was placed on the Bad Asses. For the second season in a row, CT made it to the finale, but his team could not net a victory. This set up CT on a course to win where his competitive spirit often got the best of him. But would anyone expect anything otherwise?

9 CT Wins Double Agents

‘The Challenge: Double Agents’

In the newest era of The Challenge, the series was quite fond of bunching their seasons by a loose theme. Whether it was through a war of the worlds or wrapping up storylines and personal grudges, The Challenge allowed these themes to string the series along. The next exploration of a theme was built around the world of spies. For Season 36, the cast was sent to Reykjavik, Iceland for The Challenge: Double Agents. While the season was a solo battle in the sense that they didn’t have an attached partner to start, the players played with a partner of the opposite gender. Through the usage of secret votes and double agents learning the results of said votes, the season was filled with a plethora of drama. But when the elimination challenge came around, the partners would be split up, and they would each compete against a foe of the same sex. The winners could decide to remain as partners or pick a rogue agent or another player’s teammate. This constant ever-changing element caused immense tension in the house, with players often ditching their partners in hopes of upgrading to someone who could help them in the end. For CT, after losing his first partner, he found himself paired with Big T Fazakerley for most of the game.

It was a breakout season for Big T as CT helped boost her to the star she has become. But when a moment of upgrading to a stronger partner arose, CT was more than willing to drop Big T for Kam Williams. The elimination challenge was barely over before he exclaimed, “KAM” in front of everyone. It was a terrible moment for CT as he truly hurt Big T, someone he ended up making a strong connection with. He ultimately learned the error of his ways and returned to Big T before she was eliminated. CT made it to the finale with the biggest underdog of the season, Amber Borzotra of Big Brother fame. This unlikely pair ended up taking it in the end, shocking the majority alliance that slept on Amber. What this season showed about CT was his bad boy persona is forever a part of him, but he’s shown growth and the ability to understand his faults. CT truly got wiser with age.

8 CT Returns With a Dad Bod

‘The Challenge: War of the Worlds 2’

CT has had an evolution throughout his journey on The Challenge. While the majority of his evolution was through his personality and actions, there was one major change that CT endured toward the latter part of his career that had the fans gagged. In the time when dad bods were in, CT, the always exceptionally fit competitor, returned to the program with a dad bod for The Challenge: War of the Worlds 2. Why was this important? Every one of his competitors completely underestimated his ability to continue to compete.

He may have gotten soft as a person, but the rest of the cast felt CT may have gotten too soft to keep up with the new kids. When he was about to be drafted by Team USA or Team UK, Team USA passed up the opportunity to use him to their advantage because they feared his inability to perform. Well, the joke was on them! CT helped Team UK win in the end, proving looks truly are deceiving! As CT decided to truly never retire from the show that made him, he has since transformed back to the fit frat boy fans originally knew him as.

7 CT Punches Davis Mallory

‘Real World/Road Rules: The Inferno 3’

As one of the only cast members to complete the Inferno series trifecta, there was something in the air in Cape Town, Africa that set CT off. Or maybe it was just him living up to being a Bad Ass again. Only mere minutes into the first episode of Real World/Road Rules: The Inferno 3 did CT leave his mark. On the face of Davis Mallory. Perhaps testing the limits of his Bad Ass moniker, CT allegedly asked Davis if he could take a punch. The poor boy said yes. So CT felt the need to see if it was accurate. Surely Davis didn’t expect CT to take action. But he did, and thus CT was kicked out of the house almost immediately.

At first, CT drunkenly denied his action, but production had to step in and remove him from the game. CT’s disqualification was a dark stain on the rising star. The physical attack may have shocked many, but it still somehow stayed true to his character at the time. You’d think that it would prevent him from ever returning, but surely CT would get a second chance. Put a pin on this for a moment.

6 CT Appears in Honor of Diem Brown With Her Sister

‘The Challenge: Battle of the Bloodlines’

Diem Brown was a beloved character on The Challenge thanks to her triumphant journey battling cancer while competing season after season. Aside from her true grit and drive, a major part of her journey on the show was the romance that blossomed between her and CT. Sadly, Diem passed away from her long battle with cancer in 2014. Diem’s passing took a toll on many who knew her, and to honor Diem, it was apropos that The Challenge paid tribute to the star during The Challenge: Battle of the Bloodlines.

During a challenge that took place in a mud pit, similar to the challenge where Diem removed her wig on Real World/Road Rules: The Duel, the show brought in CT and Diem’s sister, Faith Brown, to celebrate her life and journey on the show. It was a truly humanizing moment for CT as he appeared only a season prior with Diem in The Challenge: Battle of the Exes II. It was a vulnerable moment for the man who truly loved her.

5 CT Knocks Out Adam King

‘Real World/Road Rules: The Duel II’

Time to pull out that pin! After taking a season break from the show, CT was invited to return for Real World/Road Rules: The Duel II. Set in the beautiful locale of Queenstown, New Zealand, this was a chance for CT to turn things around. But following a troubled relationship that ended with Diem Brown, he was on edge, so any mention of his ex was destined to set him off. After questioning his loyalty to Diem Brown, Adam King, CT’s former The Real World: Paris roommate, felt the rage of a man who was still very much hurt.

The two had issues in the past, especially during their time in Paris, but this moment exposed a lot of damage these two had experienced in their friendship. The fight caused an immense explosion throughout the house as both the production team and their fellow competitors attempted to break them apart. Adam essentially became a human punching bag for CT. Between doors and furniture being destroyed, a battered Adam was rushed outside, but CT was on the prowl. This incident reached a point where some viewers felt that CT could have murdered him. There was no tolerance for this moment and both men were removed from the game. It was another dark moment on CT’s resume, but this moment did help spawn a rivalry that would unite the two again years later.

4 CT Teams Up With His Biggest Rival

‘The Challenge: Rivals’

The Challenge has had a fondness for testing the limits of individuals through extraordinary challenges and wicked themes. And nothing was more dastardly than when 14 teams of rivals were brought together to compete as pairs for the ultimate cash prize. The Challenge: Rivals kickstarted a new trend of themed seasons based around partners. After a few seasons away, CT was invited back to try again. His demeanor had certainly started to soften up, but his very last time on the show was when he was disqualified for punching Adam King.

So who better than to pair him then with the man who was at the other end of his fist, Adam! After years of animosity and tension, this season’s format forced the two to need each other in order to succeed. To say it was a change of character would be an understatement, as CT and Adam actually forged a strong bond with one another. Adam did have a fear of letting CT down for fear of his rage, but CT truly was a champion for his partner. Sadly for these former rivals, they were eliminated halfway through the season, but it did allow for a new era of CT to begin.

3 CT Wins His First Challenge

‘The Challenge: Rivals II’

CT is a competitor at heart. Whether it’s on The Challenge or The Traitors, he knows how to play a game. Due to a strong group of competitors, alliances that served as the team’s downfalls, and his reputation as a hothead, it wasn’t enough for CT to reach the finale. He wanted to win! Well, the ninth time’s the charm! Like Wes Bergmann, they both had a lot of rivals to choose from to be paired with for The Challenge: Rivals II, but these two finally had the opportunity to rely on one another to net CT a victory.

Their rivalry stemmed back to Real World/Road Rules: The Duel when Wes aided in taking CT down. Their feud reached a boiling point as they both threw jabs regarding their relationships at the time. This lingering aftermath seeped into years of conflict in future seasons. But when fate paired them up, The Challenge united two of the strongest players ever to form a powerhouse team. It was a dominating season for Wes and CT as they were able to squash their beef, for now, and help CT win his first challenge. It truly was another moment that aided in CT’s growth as a character on the show and in reality.

2 CT Backpacks Johnny Bananas

‘The Challenge: Cutthroat’

During CT’s first big away period from the show, fans clamored to see the competitive beast back on their screens. But knowing how his last two appearances ended with him being removed from the house due to physical violence, his placement on the series was up in the air. He needed something to redeem his past. So the flagship series gave him a second chance in a very minimal way; and let’s just say this, this monumental moment in The Challenge‘s history changed the course of CT’s career. For its twentieth season, a new format of The Challenge was implemented as three teams, chosen by draft, competed in Prague, Czech Republic.

The theme for The Challenge: Cutthroat revolved around European biohazard elements, which included an elimination arena called the Gulag. One of the recurring elimination challenges was called Back Up Off Me. In this challenge, competitors are connected back to back, and they have to reach the other side of the course and knock a barrel over. The winner would remain in the game. But there was one instance where this game was played with a twist. The two nominated players for the Gulag did not face off together, they were forced to compete against a heavy hitter. For the women, it was Tina Barta. For the men, it was the return of CT Tamburello. For this version of the challenge, the Gulag player who bested the heavy hitter in the fastest time would win. That is if they can beat them. CT came in with a fire and drive to show he was still one of the best competitors the game had ever seen. In what is forever known as the Bananas Backpack, CT beasted Johnny Bananas by literally lifting them both off the ground as CT stampeded to his intended target, tossing Bananas straight into the barrel. It is easily one of the best eliminations in the history of the program.

1 CT and Diem’s Romance

‘Real World/Road Rules: The Duel’

The most beautiful and revered romances to ever come from The Challenge all started during Real World/Road Rules: The Duel. Boy meets girl. Girl falls for boy. And the rest was history. CT Tamburello and Diem Brown‘s relationship throughout their time on The Challenge is one of the most beloved things to come from the program, beyond the competition aspect. CT fell for Diem quite quickly, but when he blushed talking about her GI Jane moment during The Duel, fans knew this wasn’t just a showmance. These two individuals were destined for love. CT was a comfort to her during a difficult time, as she came onto the season following her time in chemotherapy. For years, the two were off and on, and whether the action occurred on or off-camera, it affected CT greatly in the game. They were tasked to work with one another for The Challenge: Battle of the Exes, in which they would place second. One of the challenges during the season was called “Race to the Altar,” which got fans eager to see this couple get back together, but enough time had passed when they knew it wasn’t meant to be.

Following a second diagnosis of ovarian cancer, Diem was determined to make the best of a negative situation. They both appeared in The Challenge: Rivals II, where CT still displayed a fondness for Diem. They were fortunate to play together one last time in The Challenge: Battle of the Exes II. Unfortunately, their time was cut short following a medical situation that forced Diem to head to the hospital, causing them both to leave the game. Sadly, Diem passed in 2014. CT and Diem’s romance was truly a game changer. A new version of CT was developed. While they may not have worked out in the end, they proved to viewers that love is real on reality television.

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