As Penn now attempts to navigate the legal issues that continue to hound him and reflects on what he accomplished inside the cage, a look at a few of the rivalries that helped him carve out a legacy:
Jens Pulver
What was supposed to be a coronation for Penn turned into affirmation for Pulver, as “Lil’ Evil” retained his lightweight championship with a majority decision over the favored Hawaiian in the UFC 35 main event on Jan. 11, 2002 at the Mohegan Sun Arena in Uncasville, Connecticut. Judges Douglas Crosby and Tony Mullinax cast 48-45 and 48-47 scorecards for Pulver, while Jeff Mullen scored it a 47-47 draw. Penn had won his first three fights under the UFC banner—Joey Gilbert, Din Thomas and Caol Uno were the victims—in less than eight minutes combined and appeared to have the upper hand against the champion early on, nearly submitting him with an armbar at the end of the second round. However, Pulver’s indomitable will slowly took over, as he held his own with Penn in both the standup and grappling exchanges in the later rounds. While the decision remains somewhat controversial to this day, no one can discount Pulver’s efforts in what became his signature victory. By the time they met for a second time, Pulver was a shell of his former self and lacked the wherewithal to deal with the Hawaiian’s otherworldly skills. Penn submitted the Pat Miletich protégé with a second-round rear-naked choke at “The Ultimate Fighter 5” Finale on June 23, 2007. It was Pulver’s final appearance inside the Octagon.
Matt Hughes
Hughes had a runaway-train feel about him when he risked the welterweight crown against Penn in the UFC 46 co-headliner on Jan. 31, 2004 at the Mandalay Bay Events Center in Las Vegas. One opponent after another had yielded to his toxic blend of power wrestling, ferocious ground-and-pound and technical grappling, as he had rattled off five consecutive title defenses. Penn was one of the most gifted fighters the sport had ever seen and had rebounded from a majority decision loss to the aforementioned Pulver, his victories over Paul Creighton, Matt Serra and Takanori Gomi sandwiched around a five-round draw with Caol Uno. Most seasoned observers believed Hughes was too strong for the popular but undersized Hawaiian. They could not have been more wrong. Penn took it to the champion on the feet, and when Hughes stumbled after whiffing on a left hand, “The Prodigy” dumped him to the mat. Penn passed guard, advanced to the back and cinched a rear-naked choke. Hughes had no choice but to tap with 22 seconds left in the first round, as he emerged from the choke with a blank stare and reluctantly passed the torch. Penn made it look easy. They met twice more in the ensuing years. Hughes exacted a measure of revenge with a second-round technical knockout at UFC 63 in 2006 before Penn closed the book on their trilogy with a 21-second knockout in 2010.
Sean Sherk
Penn tied up some loose ends and retained the undisputed lightweight championship in the UFC 84 headliner, as he wiped out Sherk—“The Muscle Shark” had been stripped of the title less than a year earlier due to a positive test for performance enhancers—with a third-round knee strike and follow-up punches on May 24, 2008 at the MGM Grand Garden Arena in Las Vegas. The Hawaiian controlled the majority of the match with a punishing jab, keeping Sherk at bay while denying both of his attempted takedowns. The damage started to pile up in the third round, with Sherk bleeding from cuts near both eyes. In the waning seconds, Penn charged at the Greg Nelson protégé and blasted him with a flying knee that sent him careening into the fence. A semi-conscious but defenseless Sherk was then met with rapid-fire punches until the horn sounded. Penn declared he was done, and referee Mario Yamasaki agreed. “The Prodigy” connected on 69 percent of his significant strikes in the 15-minute affair, outlanding Sherk by a 122-46 margin.
Frankie Edgar
A man who had been urged by many to drop to 145 pounds ended the reign of the sport’s most dominant lightweight, as Edgar used his speed, movement and a pair of takedowns to outpoint Penn in the UFC 112 co-main event on April 10, 2010 at the Ferrari World Concert Arena in Abu Dhabi, United Arab Emirates. Scores were 50-45, 48-47 and 49-46, all in Edgar’s favor, as he laid claim to the undisputed lightweight crown. Bearing bruises under both eyes, Penn seemed resigned to defeat as he awaited the decision from the judges. He had not lost as a lightweight in more than eight years. Edgar grounded the Hawaiian with authority and punctuated his stunning triumph with a strong fifth round. There, he consistently beat the champion to the punch and stayed out of danger. Edgar utilized feints and a multipronged standup attack throughout the competitive five-round encounter. Penn landed the more powerful punches but never seemed to shake the resolve of the challenger, who appeared unfazed by the pound-for-pound great’s considerable aura. Penn again relied heavily on his stiff left jab and flurried late, but he seemed to slow noticeably after chasing “The Answer” for the full 25 minutes. Edgar won both rematches against “The Prodigy,” leaving no doubt as to who was the superior mixed martial artist. He took a unanimous decision from Penn at UFC 118 a little more than four months later, then buried him with third-round punches at “The Ultimate Fighter 19” Finale in 2014.