Leopoldo was also a very talented middle linebacker in football, and attended the University of Washington on a partial athletic scholarship, but he was unprepared for college, and returned to Hawaii shortly after.
Although Gracie tried to take him down at all costs, Kimo stayed firmly on his feet, and even managed to capture his back in a failed trip.
Royce reversed it and mounted him, but only briefly, as Kimo flipped Gracie over and landed multiple headbutts through his guard.
[3] Even though Kimo lost, Royce couldn't fight two other bouts he had that night, and had to forfeit his match against Harold Howard.
Kimo and his cornermen Joe Son featured a controversial moment that very night, when they jumped on the cage after Royce's forfeiting and started celebrating among the audience's chants.
He won his first fight against UFC 7 finalist Paul Varelans, but withdrew from the tournament after the win due to exhaustion.
He then traveled to Japan and fought the former 3 time UFC champion Dan Severn in the inaugural Pride Fighting Championships event.
Kimo began the contest aggressive, securing a strong takedown and controlling Kohsaka for the first six and a half minutes.
[5] After a four-year break from mixed martial arts, Kimo won a warm up fight against Tim Lajcik in the WFA in 2002.
As Sapp came forward with clubbing punches and knees, Kimo fought back with countering hooks, and the two fighters exchanged knockdowns in the first round.
[8] Fighting his final kickboxing match to date at K-1 Burning 2004, Kimo endured a knockout loss to former amateur boxing champion Hiromi Amada.
[12] At a July 21, 2009, press conference Leopoldo denied anyone close to him created the rumor, he also expressed his desire to return to fight one last time.
[13] Kimo is well known for his Christian beliefs: he sports many religious tattoos, and entered the arena at UFC 3 carrying a large cross on his back.