One of the sport’s most gifted, charismatic and accomplished competitors, Penn’s considerable exploits inside the cage have been overshadowed by his lack of commitment to training, inconsistent performance, run-ins with the law, bizarre behavior and a precipitous late-career plunge that saw him suffer seven consecutive defeats between Oct. 29, 2011 and May 11, 2019. While the Hawaiian has yet to formally announce his retirement from mixed martial arts, he turned 42 in December and has not fought since he lost a unanimous decision to Clay Guida at UFC 237 nearly two years ago.
As observers and fans continue discuss Penn’s place in history, here are five things you might not know about him:
1. He rarely backs down from a challenge.
Penn has faced former Ultimate Fighting Championship, Pride Fighting Championships, Bellator MMA, Strikeforce and World Series of Fighting titleholders in 18 of his 32 career bouts. He went 6-11-1 on those appearances, with wins over Matt Hughes (twice), Matt Serra, Takanori Gomi, Jens Pulver and Sean Sherk.
2. His hat was hung in many places.
Never one to put down roots, Penn has competed in five different weight classes: featherweight (145 pounds), lightweight (155), welterweight (170), middleweight (185) and heavyweight (265). He topped out at 191 pounds for his March 26, 2005 encounter with Lyoto Machida under the K-1 Hero’s banner.
3. Judges oftentimes were hostile to his efforts.
Penn has gone to the scorecards 14 times in his 32-fight career. He owns a 3-9-2 record in those bouts, his only victories coming against Serra, Rodrigo Gracie and Renzo Gracie.
4. His feats will stand the test of time.
Penn remains one of only seven competitors in Ultimate Fighting Championship history to capture titles in multiple weight classes. Randy Couture, Conor McGregor, Georges St. Pierre, Daniel Cormier, Amanda Nunes and Henry Cejudo were the others. Penn held the welterweight championship from Jan. 31, 2004 to May 17, 2004 and the lightweight crown from Jan. 19, 2008 to April 10, 2010.
5. He was an offensive marvel who could bury opponents in a blink.
Armed with world-class Brazilian jiu-jitsu and devastating knockout power, Penn has six first-round finishes to his credit. He put away Joey Gilbert with punches in 4:57 at UFC 31 on May 4, 2001, cut down Din Thomas with a knee strike and follow-up punches in 2:42 at UFC 32 on June 29, 2001, punched out Caol Uno in 11 seconds at UFC 34 on Nov. 2, 2011, submitted Hughes with a rear-naked choke in 4:39 at UFC 46 on Jan. 31, 2004 and punched out Hughes in 21 seconds at UFC 123 on Nov. 20, 2010.