#2 Kevin Jackson - Olympian gold medalist (Freestyle Wrestling)

Kevin Jackson is one of the most decorated Olympian wrestlers on this list. Apart from winning gold at the 1992 Olympics, he is a two-time World Champion, a three-time World Cup gold medalist and a two-time Pan American Games gold medalist.
Jackson started his MMA career with a bang, winning his debut at Extreme Fighting 4 and the UFC 14 middleweight tournament. However, the Olympian suffered a loss, and fell short of having a successful MMA career.
Get the latest updates on One Championship Rankings at Sportskeeda and more
Kevin Jackson was submitted in 16 seconds by Frank Shamrock at UFC Japan in the fight for the inaugural UFC light heavyweight championship. Three months later, the Olympian suffered another submission loss, this time at the hands of Jerry Bohlander at UFC 16.
After moving on to another MMA promotion and picking up a win in May 1998, Kevin Jackson retired from the sport and eventually took up coaching.
#1 Makoto Takimoto - Olympian gold medalist (Judo)

Makoto Takimoto won gold at the 2000 Summer Olympics in judo in the half-middleweight category. Takimoto considered switching to MMA after watching a fellow judoka enjoy success in the sport in 2004. The welterweight Olympian announced that he would make his debut in Pride Shockwave 2004 against any non-Judo fighter in any weight class.
The Olympian made his MMA debut against former Sumo wrestler Henry Miller, a bout he won via unanimous decision, outstriking and outwrestling a heavier opponent. In his first six fights, all of which were in Pride, Takimoto amassed a 3-3 record.
Despite a 6-5 record, Makoto Takimoto cannot be said to have had a successful MMA career. Since losing his first fight against Kiyoshi Tamura in 2005, the Olympian has lost against almost every top opponent he has faced. He did defeat former UFC middleweight champion Murillo Bustamante in 2007, but his MMA career can best be described as modest.