6. Matt Lindland
Few fighters have had as strange and diverse a career as Lindland. The accomplished collegiate wrestler at the University of Nebraska won the gold at the 1994 Pan-American games as a freestyle wrestler, but he found his greatest success in the Greco-Roman category, with multiple Pan-American championships, a second-place finish at the 2001 world championships and, most notably, a silver medal at the 2000 Olympics.
Between 2004 and 2009, Lindland went undefeated as a middleweight and 10-2 overall, with the only losses to top pound-for-pound fighters Quinton Jackson and Fedor Emelianenko outside of his own weight class, and “The Law” could make a legitimate claim as one of the top 185ers in the world. All of that came crashing down with a terrifying knockout loss to Vitor Belfort in the defunct Affliction promotion in a bout that lasted only 37 seconds. Lindland went 1-3 in his last four fights before retirement.
Lindland had a long, strange and highly accomplished career -- we have not even touched on his business ventures, which ranged from allegedly stealing medical marijuana grown on land he owned to used-car dealerships and a successful run for the Oregon House of Representatives -- and one that deserves respect for its incredible diversity and longevity.
Number 5 » Ben Askren