You, Me, and Jay Dee: The Ballad of B.J. Penn

Virtuoso fighter B.J. Penn hasn’t done all he could have done in his career. Have you?
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We shouldn’t be able to relate to Jay Dee “B.J.” Penn in any meaningful way. A two-division UFC champion and the first American to win in a black belt division at the International Brazilian Jiu-Jitsu Federation World Championships, he presents the same brand of alien greatness that makes all virtuosos inherently unknowable. The slack and gaping appreciation that Penn is so capable of conjuring is supposed to make him an island unto himself: How could any of us begin to understand someone we know within the context of sporting feats none of us could ever even begin to approach?

And yet Penn is knowable, and painfully so, in a way that we all are but ignore for the sake of our mental health. Knowing Penn is about the unspoken knowledge that we are all but guaranteed to look back on our lives and know we left something on the table. And if it seems odd, if not outright ignorant, to say it about arguably the most gifted fighter any of us will ever live to see, Penn left a lot on the table. At 33 years old, his career isn’t over yet, but he is facing its twilight, and to look back on his 16-8-2 record is to be struck by the selfish realization that there could have been so much more. Especially after considering how perfectly it all began.


In 2001, the year after winning being awarded his Brazilian jiu-jitsu black belt and almost immediately winning an IBJFF world championship at the improbable age of 21, Penn was signed by the UFC despite not having a single professional fight to his name. Save his impeccable grappling credentials, all Penn had going into his UFC 31 debut against Joey Gilbert was hype and an audacious nickname: The Prodigy. Gilbert was summarily outclassed, and finished within the space of a round. It was like watching a Renaissance master forced to paint on a substandard canvas, the talent obvious but the skill clearly requiring the right circumstance to show through in full. This is how it goes with great combat sport prospects—they are expected to feast on mediocrity until doing so comes to seem painfully unfair to the mediocre. This is not the path Penn allowed himself to go down and, for better and worse, it’s the path that both enabled and limited the fullest expression of his greatness.

Less than two months after his UFC debut, Penn entered the cage against veteran lightweight contender Din Thomas, a matchup that raised eyebrows from the moment it was announced. Thomas held a 12-1 record at the time, including  a win over the UFC’s then-lightweight champion Jens Pulver. This was not the kind of fight a 1-0 prospect is supposed to take, no matter how talented they may be. Thomas was knocked out in all of 2 minutes and 42 seconds.

Four months later,  Penn again put the world on notice by knocking out Caol Uno in 11 seconds flat. This was the same Caol Uno who lost a nip-tuck decision to Pulver that same year in the UFC’s inaugural lightweight title bout. The Brazilian jiu-jitsu wunderkind was knocking out the best lightweights in the world, and doing so with seemingly minimal effort. Mike Tyson comparisons were commonplace but ill-fitting. Even at his most dominant, you could see the physical strain fueling Tyson’s ferocity. To see Penn fight was to see Michael Jordan’s iconic mid-game shrug of bemusement expressed in the least forgiving corner of the sports world. Penn was Penn, doing what Penn does. And so we shrugged along with Penn, knowing that there was nothing else to be done.


After the Uno fight, Pulver was quickly scheduled to defend his title against Penn, and entered the bout a 3-1 underdog to a 23-year-old with less than two full rounds of live cage time and less than a calendar year of professional fighting to his name. The only surprise through the first two rounds of the fight was that Pulver survived them. Maybe that shouldn’t have surprised anyone: Just as greatness was Penn’s calling, survival was Pulver’s.

Born to an alcoholic father fond of unimaginably sadistic abuse, Pulver’s childhood was a nightmare. Born to an affluent Hawaiian family that bankrolled his interest in combat sports, Penn’s childhood was a dream by comparison. Neither of these things mean something universal, but they do mean something to each of these people. While Pulver knew and embraced the grind of facing a superior foe, Penn fought like someone who didn’t know he was supposed to embrace that grind. He shrank ever so slightly in the face of Pulver’s willingness to endure more than him, and after five rounds, the judges called the bout for the champion.

Here’s the thing: While professional fighting is not some glorified blood sport, it’s also not golf. It will test you in a way few things can, and there isn’t a MMA trainer alive who doesn’t have a novel’s worth of stories that end with rich kids leaving their gym in tears. Penn does not belong in any such story, but he was, all the same, unaccustomed to being tested. In a sport full of brutal ironies, the crowning one was this: Penn was too good for his own damn good.

And this is the story of Penn’s fighting career—stretches of incomparable greatness interrupted by moments that call into question not his greatness, but his willingness to be great. The same man who botched his first shot at lightweight title redemption by going to a listless draw in a rematch with Uno would also choke out then-welterweight kingpin Matt Hughes in the space of a round. The same man who no one wanted to spar or roll with would also become infamous for his lackadaisical training regimen. Just as Milhouse wondered when Itchy and Scratchy would get to the fireworks factory, MMA fans were left to wonder more or less the same about The Prodigy.

Penn did get there. Probably about five years late, but he got there and it was glorious. In the 2008 bout in which he finally won the UFC lightweight title, Penn choked out Joe Stevenson so hard that a geyser of blood erupted from the man’s head. Sean Sherk, a former welterweight title challenger and undefeated lightweight, followed and, well, this happened.

Of course, just as it seemed Penn was going to put it all together, it all fell apart. At UFC 94, Penn inexplicably took a break from what felt like the beginning of a dominant lightweight title run to rematch UFC welterweight champion Georges St-Pierre. It was pure folly, which  St-Pierre exposed by manhandling Penn for the four rounds it took before The Prodigy’s cornermen had the fight stopped on his behalf. This could have been a good thing for Penn, had it finally made it clear to him that he is not meant to fight welterweights. It could have made clear that he is meant to lord over the lightweight division, and that he should set his mind and body to that task while he still can. For one golden year, it looked like he would.


2009 saw Penn dismiss Kenny Florian and Diego Sanchez, both former welterweights in the prime of their careers, like they were a pair of regional no-hopers. The disparity in skill and talent between Penn and the division was simply stark. To be a lightweight title contender back then must have been like being trapped in a John Carpenter movie: Make it to the end, and the only thing awaiting you is the existential knowledge that the circumstance of your demise is the only guarantee you’ve earned. Like I said, it was fucking stark.

So, at long last Penn was on his way to doing the one thing we had not yet seen him do, and it looked like we’d finally get to see him dominate the division he was always so capable of dominating. Up until then, his potential was realized only in fits and starts interrupted by Penn’s tendency to seek out challenges too great and fail to show up for the challenges at hand. The hope was that ignoring challenges too great would bring those challenges at hand into perfect focus.

That theory went to shit almost immediately. A match with Frankie Edgar, an undersized lightweight who was given a title shot practically by default, ended in controversy when Edgar’s hand was raised after five rounds. While Penn’s performance was far from his best, most media members had scored the bout for him and felt Edgar was the beneficiary of MMA’s notoriously shoddy judging. An immediate rematch followed, in which Penn got his ass kicked. Which made enough sense.

Edgar, like Pulver, will be remembered as a reasonably talented fighter who owed a great deal to his willingness to make up for his faults with an unsurpassed dedication to maximizing his gifts. Penn, like only Penn could, will be remembered as a brilliant fighter who owed us nothing, but perhaps owed himself and his gifts so much more. What else can be said of a fighter who went eight-plus years between losses at lightweight yet never won more than three fights in a row? It is maddening. But that's B.J. Penn.


Since losing consecutive lightweight bouts for the first time in his career, Penn has competed exclusively at welterweight and gone 1-1-1. His next bout is on Saturday, and it’s against a welter he’s not expected to defeat: Rory MacDonald, a freakishly talented 23-year-old who, unlike Penn, responded to the disappointment of his first professional loss by becoming an even greater version of himself.  No one questions whether or not MacDonald will put in the work it takes to win a fight. Everyone questions whether or not Penn will do the same.

Even if Penn wins—and he is always tantalizingly capable of doing so—it will be just another flash of greatness. We already know he doesn’t have the size to consistently defeat elite welterweights, and that’s not about to change. As for elite lightweights, Edgar put to rest the belief that Penn could lord over that division at will should he ever set aside tilting at welterweight windmills.

And for as much as I would have liked to see Penn realize the fullest version of his potential, at the end of the day, I still say fuck it. There is a legacy worth remembering here, imperfect as it may be. No, Penn does not get a seat at the same table as Georges St-Pierre or Anderson Silva or Fedor Emelianenko. However, will you get a seat at the same table where the greats of your profession sit?

I won’t, same as Penn. You probably won’t either. The difference is that you and I will likely never come as close as Penn did. I’m okay with that, and you should be too. As for Penn, I hope he’s better than okay with it. I hope he grows old and fat on a Hawaiian beach and looks back on the handful of days he lived as the greatest fighter in the world with a smile on his perpetual baby face. Unlike my own theories on how great he could have been, those days of greatness were real, and they are worth remembering.

Illustration by Brandy Jefferys.

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