10 Seasons: Battle of the Sexes 2, Inferno II (Final), Gauntlet II, Fresh Meat, The Duel, Inferno III (Win), The Island (Win), The Ruins (Win), Cutthroat, Dirty XXX (2nd place)

8–4 Elimination Record

43 Challenge Wins

Daily Challenges: 8.5/10

Eliminations: 9/10

Finals: 7.5/10

Politics: 8.5/10

Perhaps pound-for-pound the greatest male competitor of all time, Derrick has been proving people who underestimate him wrong his entire career.

Although he had a relatively early exit on his first season, Battle of the Sexes II (despite performing well), Derrick made it to at least the final elimination in eight of his next nine seasons.

He made his first final with the Bad Asses on Inferno II, but Derrick established himself as a legend on Gauntlet II. After running his mouth got him thrown in to the first elimination, Derrick became the new Veterans’ captain by taking out Adam Larson in Name That Coconut. He proceeded to go on one of the most epic runs in Challenge history, knocking out Ace, Syrus and Brad — all in physical eliminations.

But he couldn’t tie Sarah Greyson’s (and eventually Wes/Casey’s) record of five elimination wins in one season, falling to Timmy right before the final.

His streak of heartbreaking losses continued on Fresh Meat and The Duel. Derrick and Diem won three daily challenges on Fresh Meat, but they were sent into the last elimination by Tina/Kenny to face Darrell/Aviv, where they lost with 75 more pounds of weight than their opponents.

Derrick competed well on The Duel, including winning the tough Push Over challenge, but he again lost in heartbreaking fashion to Wes in my personal pick for the greatest elimination of all time.

He finally earned his first victory on his sixth season, The Inferno III, where he was brought in as a replacement for CT. He then won his next two seasons, joining the winning boat of Kenny, Evelyn and Johnny on The Island, then aligning with JEK to stay out of elimination throughout The Ruins.

On Cutthroat, Derrick and Johnny were essentially co-captains of the top-heavy blue team, which won just two missions. Nobody could argue Derrick’s performance was the reason for blue team’s lack of success, however, as he again was one of the best players on his team and delivered another classic highlight in his performance in the Riot Act challenge.

Derrick ended Brandon’s three-elimination winning streak in Handcuffs, but lost Pole Me Over to Tyler due to his huge size disadvantage. It was the third time in his career Derrick went home right before the final.

After not competing for seven years, Derrick returned on Dirty 30 and didn’t miss a beat.

Once again he was one of the top competitors and stayed out of elimination for most of the game, until he was sent in by Hunter and faced Bananas in The Reel World, where he pulled out a victory. He took out Hunter and Tony in the final purge challenge, before finishing second in the final behind Jordan.

Derrick was the only man to not go to the Redemption House the entire season (besides Nelson, who was ejected for hitting Derrick).

Despite his size, Derrick is one of the most tenacious competitors in the show’s history and has elimination wins over strong competition like Adam Larson, Syrus, Brad, Tyler, and Bananas (not to mention his epic victory over Joss on Vendettas), with his only losses coming against Timmy, Darrell/Aviv, Wes and Tyler.

Politically, I think Derrick is extremely underrated. He is sometimes called a lapdog for the JEK alliance, but since aligning with them on The Island he has been in just three eliminations, including earning a free pass to the finals on The Ruins. Even earlier in his career he was aligned with the big dogs, partnering with Darrell and Theo on Fresh Meat and Evan, CT and Brad on The Duel.

However, he had some bad moments early in his career, like blowing up in the first veteran’s deliberation on Gauntlet II which got him sent in against Adam L, and his decision to throw in Theo/Chanda blew up in his face on Fresh Meat.

Derrick’s championships aren’t super impressive since they were all in team formats and he only went into elimination one time (although he did earn his key by beating Bananas and Abe on The Island), but he has other strong seasons like Inferno II, Gauntlet II, Fresh Meat, Cutthroat and Dirty XXX to compensate.

Derrick versus Darrell is essentially a toss up to me.

They are both excellent competitors and savvy political players who know how to fly under the radar.

What gives Derrick the edge for me is that he doesn’t have the black marks on his record like Darrell does going out early on Fresh Meat II and Dirty XXX, and I also think he’s performed better in daily challenges over the course of his career.

Derrick is the most tenacious competitor in Challenge history, and with a track record that consists of a three-peat in the middle of his career and no bad seasons in between, he earns his spot in the top seven.

Rankings

25. Nelson Thomas

24. Paulie Calafiore

23. Leroy Garrett

22. Frank Sweeney

21. Jamie Murray

20. Tyler Duckworth

19. Hunter Barfield

18. Timmy Beggy

17. Dan Setzler

16. Zach Nichols

15. Abram Boise

14. Mike Mizanin

13. Theo Vonkurnatowski

12. Brad Fiorenza

11. Alton Williams

10. Wes Bergmann

9. Darrell Taylor

8. Derrick Kosinski

7. Kenny Santucci

6. Mark Long

5. Jordan Wiseley

4. Evan Starkman

3. Landon Lueck

2. CT Tamburello

1. Johnny Devenanzio