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The Challenge champion Darrell Taylor won his first four seasons, earning nearly $250,000. However, he hasn’t had much luck in recent years. Following his elimination from Double Agents and shortly before appearing on spinoff All-Stars, Taylor admitted he might not return for another season in his exit interview.

Johnny "Bananas" Devenanzio and Darrell Taylor training during The Challenge XXX: Ultimate Fan Experience
Johnny “Bananas” Devenanzio and Darrell Taylor training during The Challenge XXX: Ultimate Fan Experience | Lars Niki

Darrell Taylor won four seasons of ‘The Challenge’

Road Rules: Campus Crawl star Darrell Taylor made his debut on spinoff The Challenge for The Gauntlet in 2003. The California native won as a rookie and then returned for The Inferno, The Inferno II, and Fresh Meat, winning them all.

He also performed well in The Ruins, likely on his way to claiming his fifth win, but a physical altercation with another housemate disqualified him before the finals.

The four-time champ returned for Fresh Meat II but was the first taken out of the competition. He then invaded the following season, Invasion of the Champions, and eliminated veteran Zach Nichols and multi-season champ Johnny “Bananas” Devenanzio before getting taken out himself.

The Inferno winner also competed in Dirty 30, where he was purged out of the competition.

Taylor couldn’t protect his gold skull during season 36

Following a three-year break, the four-time champ returned for Double Agents and partnered with rookie Amber Borzotra. Thanks to her dominating alliance with other Big Brother stars, the two flew under the radar but worked well together, winning one daily mission.

Although his partner got blindsided into elimination against Amber Martinez, the rookie came out on top. A couple of weeks later, he unexpectedly had to face off against Devin Walker, who called him out, during a double men’s elimination.

However, he solved the puzzle faster, earning his gold skull and ticket to the finals. Shortly later, most of the house voted in Taylor, who didn’t have as many connections, to battle against Cory Wharton.

The Real World veteran ended up beating the multi-season champ, stealing his gold skull, and sending him home.

Taylor might have returned for the last time in ‘All Stars’

Following his elimination, the California native gave Wharton props for his speed and called him the “better man” that night. He admitted the loss was a “hard spill to swallow,” especially before the finals but recognized he couldn’t have done anything differently.

Although Taylor is sad to walk away, he noted his excitement to reunite with his family.

The four-time winner also said he would want to return for another shot but isn’t sure because of how “hard” it is to leave his wife and kids for an extended period.


‘The Challenge’: Devin Walker Explains Why He Chose to Battle Darrell Taylor

Shortly after filming Double Agents, Taylor agreed to come back for the upcoming The Challenge: All-Stars, a spinoff featuring only old school players.

His appearance on the show might be his last on the series as the veteran, though he loves competing, seemingly would like to spend time with his family instead.

Currently married to Milasent Hernandez after dating for 10 years, the couple runs a gym together. They also have two kids, a son, and a daughter. The Challenge: All-Stars premieres Apr. 1 on Paramount+.