Twice, actually. And three if we count his loss to Diego Sanchez in the finale of the inaugural season of The Ultimate Fighter (TUF). Always the groomsman, but never the groom.
The unlikely mixed martial arts (MMA) superstar from Brookline, Mass., has another chance to reel in his big white whale once again tonight when he takes on arguably the top pound-for-pound fighter in the sport today, Jose Aldo, in the co main event at UFC 136: "Edgar vs. Maynard 3."
Florian wore out his welcome at lightweight despite an impressive record (13-3) that he compiled over the course of five action-packed years. The proverbial straw who broke "Ken Flo's" 155-pound back was none other than current number one division contender, Gray Maynard, who earned a three-round unanimous decision win over the ESPN MMA Analyst in Aug. 2010.
With two losses in two championship fights, as well as another to a top-ranked "Bully," a move down in weight was perhaps his only viable option. And with just one win under his belt, a unanimous decision over Diego Nunes earlier this year at UFC 131, Florian was already back in the title picture.
Now he needs to prove he belongs or risk descending into limbo once again ... and perhaps forever.
More than just that, Florian needs to prove to fans, UFC President Dana White -- who has said he "chokes" in big fights -- and even himself that he has what it takes to be a world champion. We've seen flashes of his brilliance throughout the years, whether it was his destruction of Alvin Robinson, domination of Clay Guida or Takanori Gomi's rude Octagon introduction.
Today, it's relatively easy to recall those impressive performances. But that's not really how most folks will remember Kenny Florian, especially if the third time really isn't the charm. On the contrary, he'll be remembered as one of the most talented fighter's of his generation to never win the big one.
He'd be the MMA equivalent of Charles Barkley, Dan Marino and Ted Williams.
Kenny Florian wants what featherweight champion Jose Also has. And this belt, specifically, means more to Florian than any other for so many short- and long-term reasons.
It's now or never.