"A victory is more triumphant when unexpectedly won against the odds than when confidently anticipated", writes British philosopher, A.C. Grayling.
This is the sentiment that has always been at the heart of B.J. Penn's career. For most athletes, their career plan is simple: you train for fights, then win fights, and if you're lucky, winning fights will eventually amount to a world title. However, Penn was always a departure from the familiar sports tropes.
This is the allure of Penn, the fighter. Sure he has a few books he'd like to sell to you, but he was never gonna harm your ears by boring you with his spiritual take on fighting, and the romance of samurai spirit. Nor would he frustrate fans with his sense of business and practicality, stalling negotiations over who he'd rather his next opponent be. For Penn, his attraction to prizefighting was primal; a place to establish dominance free of metaphor.
You'll be hard pressed to think of a fighter who is so universally loved by fans and fighters alike.
Unfortunately I didn't grow up watching Penn, despite catching the early UFC's at the local Blockbuster. After Vitor Belfort's early carnage, I didn't watch another UFC until Tito Ortiz vs. Ken Shamrock at UFC 40. And yet his presence always seemed felt, even without the spotlight. After all, how many times has his KO over Caol Uno been shown? A lot.
What always separated Penn from the pack was that he really was the first MMA polymath; a multi-specialist, as superior in one facet of the game over the majority of his superiors as he was in another. MMA had always had its specialists. It had Mark Coleman and Tito Ortiz to represent wrestling efficiency. There was Big Nog for submission prowess, Maurice Smith and Bas Rutten to represent striking acumen. MMA also had well rounded fighters before Penn, with Frank Shamrock standing out among the pack at the time. But it never had a fighter who could really dominate the way Penn could with the pedigree he had. Hence, very famously, "The Prodigy".
To rewind, Penn started his Brazilian Jiu Jitsu training in 1997 under the tutelage of Ralph Gracie: one of more wild-eyed Gracies. It wouldn't take him long to work his way up, eventually getting his black belt under Andre Pederneiras, and then becoming the first non-Brazilian to win the black belt division in the 2000 World Jiu-Jitsu Championship where he took the gold against Edson Diniz.
Grappling nerds sometimes like to discredit his win as a win in a weak division. There's certainly some truth to this. Royler Gracie was the man to beat in the division before Penn beat Diniz, and he was no longer competing in the division. Vitor 'Shaolin' Ribeiro, another favorite, would move up in weight that year. However, two things: one, a win is a win, especially when nobody recorded a point against you, and two, Penn had already (and quickly) established himself as a threat in the division. He was only 20 when he lost to future champ Fernando 'Terere' Augusto for a 3rd place finish in 1999. In other words, he didn't just show up arbitrarily at the Mundials.
So how did he make his UFC debut? By knocking people out. His first three professional fights (all in the UFC) were first round finishes. His MMA emergence felt reflective of his firebrand persona in retrospect, and it's not like he was beating chumps. While Joey Gilbert is a name no one will ever recall, Din Thomas and Caol Uno were established top fighters in their division.
The amusing thing about Penn's ascent is that for all of his talents, he failed to win either of his first two UFC title bouts. Against Jens Pulver he was stifled by Pulver's combination of wrestling and boxing. For those that don't remember, their first bout was all Penn in the first two rounds: an experience culminating in a little fortuity for Pulver, who was all but finished by an armbar late in the round. And then there was the Uno rematch at UFC 41. The Uno rematch (despite the draw being questionable, as many, including myself had it 3 rounds to 2 for Penn) was interesting because Penn had not yet perfected his takedown defense: something that would become a staple of his ability later in his career. Both Pulver and Uno had success getting inside, within the clinch, and putting him on his back.
The Uno fight was significant for what it would do the Lightweight division. Now fragmented, the 155 lb division was scattered. Most of it went to Japan where the competition wasn't yet easier.
Pride's Bushido shows began to showcase fighters like Tatsuya Kawajiri, (eventually) Takanori Gomi, Mitsihiro Ishida, Joaquim Hansen, and fighters like Yves Edwards and Jens Pulver would also make appearances. Penn walked his own path. Before getting back to the UFC, he took on Takanori Gomi at Rumble on the Rock 4, submitting him via RNC in the 3rd round: an organization promoted by his brother. If you were part of the Pride vs. UFC debate during this time, this was a feather in your cap if you thought the UFC was better. Not that the foundation ever made sense to begin with, but it's how hardcore fans spent their time in the early days: arguing over which organization was more talented.
When Penn decided to go up in weight to take on Matt Hughes at UFC 46, fans and observers not so much scolded the matchup as they found it curious, yet predictable. Hughes was the most dominant champion MMA had seen up to that point. He had defended his belt five times with wins over Carlos Newton, Hayato Sakurai, Sean Sherk, and Frank Trigg. If large welterweights were getting outmuscled and dominated by Hughes, what was a blown up LW gonna do?
And not just a blown up LW. For many...a fat LW. When Penn weighed in for the Hughes fight, much was made of Penn's weight. This wasn't a fighter who looked in shape. This was a fighter who looked to have spent hours at Taco Bell just to get above the 155lb weight limit. However, not of this seemed to matter when the bell rung. Penn made quick work of Hughes, landing a brutal right hand from top control after Hughes ended up on his back during a scramble, then securing a RNC for what felt like the biggest upset in the history of MMA.
This was the moment that would define Penn's career, even with the Edgar loss still fresh in everyone's memory. As usual, Penn didn't settle in. He had a contractual dispute with Dana and the UFC following his win for the WW belt, and K-1 was offering more money. A rematch with Hughes may have been attractive for the fans, and for the UFC. But it wasn't attractive for Penn. Penn had just easily and quickly dispatched Hughes. Again, the logic of Penn's appeal to all who know his name is that for Penn, it was never enough to challenge for the title. It was only enough if the challenge could never be confidently anticipated.