What 'Big Brother' Winner Has Won 'The Challenge?'

Winning a major reality competition show is an impressive feat. And to win two of them is a triumph that very few have accomplished. MTV’s The Challenge has featured numerous reality stars from different networks and television shows, including CBS’s Big Brother.

Kaycee won Big Brother 20 after rolling with her ‘Level Six’ alliance

Kaycee debuted on her first reality competition show in 2018 as a 30-year-old professional football player. She joined 15 other rookie players on Big Brother 20, including Fessy, as well as Christopher “Swaggy C” Williams, Bayleigh Dayton, Angela Rummans, and Tyler Crispen — all of who would go on to appear in an iteration of The Challenge.

The installment of the staple franchise lasted 99 days, and Kaycee made it all the way through while only receiving one eviction vote. The key to her success was three-fold. First, Kaycee used her fantastic social and political abilities to create solid friendships and alliances (which she also brought into The Challenge house). Second, Kaycee was a part of the season’s dominant alliance, Level Six, along with Tyler, Angela, Brett Robinson, Rachel Swindler, and Winston Hines.

Further, Kaycee’s background as a professional athlete and knack for tackling unorthodox competitions led her to win five of the final six Power of Vetos. She also picked up two Heads of Households, including the season’s last one during the final three.

Kaycee only sat on the block twice, including when Fessy nominated her in the eighth week. And incredibly, she was on the right side of the numbers every eviction night, meaning every person she voted to eliminate went home during that round of play.

In the end, Kaycee took home the $500,000 grand prize by beating out Tyler in the final two with a 5-4 vote.

Kaycee debuted on The Challenge: Total Madness after winning Big Brother

Kaycee’s time on Big Brother 20 was the jumping-off point for her reality television career. She hopped networks — from CBS to MTV — around two years after collecting her Big Brother winnings. She debuted in The Challenge’s 35th season: Total Madness.

Kaycee entered the individual-based season alongside her former houseguests: Fessy, Swaggy C, and Bayleigh. Kaycee quickly flexed her political and social games while also delivering physically; she picked up three daily challenge victories through season 35.

Total Madness marked the introduction of the “Red Skull” twist. Players had to win at least one elimination round that season to qualify for the final challenge. Kaycee asked the Tribunal to throw her into “Purgatory” in episode 9 so she could earn passage to the finale. They obliged, and Kaycee ultimately faced off against Challenge veteran Kailah Casillas in a contest that had them moving 100 heavy “bombs” before hitting the buzzer. Kaycee came out atop his first elimination duel while stamping her ticket to the final challenge.

After summiting a snowy mountain, Kaycee placed as the women’s runner-up behind Jenny West.

She made it to the Double Agents final as well but suffered a game-ending injury

Kaycee returned the following season — Double Agents — and would once again see the final challenge. Season 36 brought back the skull twist and was also a team-based game. It was the first time Kaycee had to work with a partner throughout the entirety of a reality competition season.

The theme incentivized players to volunteer for the “Crater” (the name of Double Agents’ elimination arena) in two ways: a win would qualify them for the final challenge, allowing them to switch partners with another team. The elimination games were individual contests.

Kaycee’s teammate changed multiple times in Double Agents. After Fessy defeated Nelson Thomas in episode 4, he stole Kaycee away from Leroy Garrett. But, their partnership only lasted one episode as Fessy’s original teammate Aneesa Ferreira took him back after she won in the Crater. The move reunited Kaycee and Leroy.

The Big Brother champion found herself in the second elimination round of her Challenge career during episode 9. That’s when she beat out another Challenge veteran, Theresa Gonzalez-Jones, to receive a Gold Skull. And, instead of choosing another partner like Fessy, Kaycee elected to stay with Leroy. They’d play as a duo all the way until the last elimination of the season; all in all, Kaycee and Leroy won five daily challenges together. However, Fessy knew he wanted to run the final challenge with Kaycee. And after Kyle Christie had his finger dislocated in their “Hall Brawl” game, Fessy reclaimed Kaycee as a partner.

But, things didn’t go the way the two Big Brother 20 veterans had planned. Kaycee suffered a knee injury during the second checkpoint of the final challenge’s first day. She was medically ejected from the game, placing fourth with Fessy.

Spies, Lies, & Allies marked the season Kaycee became a Challenge champion

The third time was a charm for Kaycee. After undergoing surgery for the injury she sustained in Double Agents, Kaycee played in season 37’s Spies, Lies & Allies. The season featured Challenge veterans and international reality television stars, including Survivor Romania’s Emy Alupei and Emanuel Neagu.

By this point, Kaycee had firmly established herself as one of the strongest female competitors in the franchise considering she was undefeated in elimination rounds and had always made it to the final.

Season 37 did away with the skull twist, meaning players returned to the tradition of avoiding elimination challenges at all costs. And Kaycee did that successfully en route to her third final and first Challenge championship.

Spies, Lies, & Allies began as a two-team game linking the international players with the Challenge veterans. It also revived the partner-stealing twist from Double Agents. Halfway through the season, the remaining players were divided into three teams, and they went at it until only eight players — four female and four men — were left.

She won one daily challenge when paired with Emanuel during the duo-based portion of Spies, Lies & Allies. Kaycee joined the “Emerald” team when the game’s format changed, which was the dominant cell. They won five of eight daily challenges.

Kaycee and the remaining field of players competed as individuals during the first part of the final challenge before switching into two cells. She was a part of the “Orange” team alongside her girlfriend, Nany Gonzalez. However, their dream of crossing the finish line together was dashed when they were forced to battle each other in a surprise elimination round. Kaycee sent Nany home empty-handed to start the second day of the final challenge.

However, the elimination round for Kaycee brought some good news. By winning, she was granted the opportunity to choose a male partner to close out Spies, Lies & Allies with. Kaycee picked CT — a Challenge legend and several-time champion — as her teammate. And it proved to be a wise decision.

After racing up a mountain to memorize a 20-digit code, Kaycee and CT ran back down and unlocked a safe before any other team. They were anointed the season’s champions by coming out on top in the final leg. They were also entitled to their share of $1 million — $500,000 each — but Kaycee and CT could split some of their grand prizes with the second and third-place finishers.

They agreed to hand over $100,00 to each duo, which gave each remaining contestant a $50,000 constellation prize.

With the win, Kaycee etched herself in the history books as the first reality star to win Big Brother and The Challenge. Spies, Lies & Allies was CT’s fifth championship win in MTV’s mainline series, and he ascended to the spot of the franchise’s top earner.

She’s competed in Ride or Dies and World Championship since

Just because Kaycee became a two-time franchise queen didn’t mean she was done appearing on The Challenge. She returned for her fourth consecutive show — season 38’s Ride or Dies — and joined the cast with her brother, Kenny, as her partner.

However, Ride or Dies went entirely different than her past experiences on The Challenge and Big Brother. Kaycee and Kenny were removed at the beginning of the game after testing positive for COVID-19. But Emmy Russ elected to leave Ride or Dies in episode 2 (which instantly eliminated her partner Nam Vo), and Kaycee and Kenny rejoined the game after being cleared to return.

Kaycee and Kenny nearly made the final challenge but were eliminated in the “Zone” in episode 15 after losing a three-duo series to Moriah Jadea and Fessy and Jordan Wiseley, and Aneesa. It was the first time Kaycee was sent packing by losing ahead of the final.

Kaycee then returned for World Championship — a spin-off iteration that ran earlier this year on Paramount Plus. Once again, Kaycee made it to the final challenge. She played half of the game alongside Survivor 35 winner Ben Driebergen and was then paired with The Challenge: Australia champion Troy Cullen after Ben was medically disqualified. Although Kaycee and Troy finished in third place, they impressed with three elimination wins. Kaycee and Ben picked up an “Arena” victory as well.

To say Kaycee’s Challenge career has been impressive is an understatement. She’s made four out of five final challenges while notching nearly 20 daily challenge wins. She’s won seven elimination rounds and has taken home nearly half a million dollars in prize money.

And it doesn’t seem like the 35-year-old reality star is calling it quits anytime soon.