Welcome back to the latest edition in our 'Undisputed Legends' series, where we take a look at some of the greatest fighters to ever set foot inside the Octagon, who never won a UFC world title.

Kenny Florian

A product of the first season of The Ultimate Fighter (TUF), Kenny Florian (14-6 MMA, 12-5 UFC) enjoyed an extraordinary career inside the Octagon, competing in four separate weight classes and challenging for a UFC title on three occasions.

“KenFlo” defeated Chris Leben to reach the TUF finale in 2006 as a middleweight, where he lost to Diego Sanchez. The performance earned him a UFC contract, and he went on to win his first three bouts in the organization—the first two at 170 pounds—before submitting Sam Stout to earn a shot at the vacant UFC lightweight title in October 2006. He was defeated in that bout by Sean Sherk.

“If I’m being completely candid, I felt that I wasn’t ready for Sean Sherk,” Florian admitted in an interview with UFC.com. “I was going out there to die, to a certain extent. I knew I was outgunned—he had all the weaponry, and I had a handgun and a knife.”

A six-fight winning streak earned Florian a second shot at the lightweight title three years later against B.J. Penn, but that opportunity also ended in heartbreak. “When I faced him, it was the perfect matchup for him in many ways,” Florian recalled of the bout with Penn at UFC 101 in 2009. “My boxing and wrestling weren’t where they needed to be, and my jiu-jitsu needed work. And I was at a pretty high level at that point. I wasn’t at the best point of my career, but I was at a pretty good level—and B.J. showed that he was far superior in those aspects. It was just the wrong time to face B.J. Penn.”

Florian regrouped and earned one more shot at UFC gold. After defeating Diego Nunes in his featherweight debut, he was booked to face José Aldo for the 145-pound title at UFC 136. Unfortunately, he suffered the same fate as in his previous title fights—a dominant defeat at the hands of one of the sport’s all-time greats.

“He was definitely the most well-rounded and most potent striker I ever faced,” Florian reminisced. “And certainly the most complex as well. The hardest I’ve ever been hit was B.J. Penn, but José Aldo was a guy with a lot of weapons. Speed is one of those things that’s very difficult to prepare for, and he was as fast as they come.”

In what turned out to be the final fight of his career, Florian became a sitting duck for a relentless barrage of leg kicks from his Brazilian opponent. “José Aldo is so quick,” recalled the TUF veteran, “and even knowing the leg kick was coming and preparing for it, he still kept landing it. I didn’t have feeling in my leg for about two months. I developed a tic where I’d rub my leg to see if I could feel anything—the nerves were just dead on the inside of my right leg for two months, and finally it came back. I checked one or two, but it was so hard to check and defend. He was brutally quick.”