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B.J. Penn accomplished a great deal during his legendary UFC career. The Hall of Famer was a two-division champion, having won the lightweight and welterweight championships.
In 2001, ‘The Prodigy’ made his professional debut in the promotion and quickly became a lightweight contender. He came up short in his first title shot against then lightweight champion Jens Pulver. But he came back stronger and defeated Matt Hughes for the welterweight championship. Penn relinquished the title due to a contract dispute and continued his career in K-1. He returned to the promotion in 2006, but didn’t have the same success at 170 lbs.
Back-to-back losses to Hughes and Georges St-Pierre resulted in him returning to lightweight. It was the right move for his career as ‘The Prodigy’ soon became the lightweight champion. He made three title defenses and was viewed as one of the top pound-for-pound fighters in the sport.
Although he fought many legends in numerous weight-divisions, there were still intriguing fights that never took place. This list will look at five B.J. Penn fights that should've happened in the UFC but didn't.
#5. Former UFC title challenger Gray Maynard
B.J. Penn vs. Gray Maynard was a missed opportunity for the UFC. Maynard had ascended the lightweight rankings following his stint on The Ultimate Fighter Season 5.
‘The Bully’ defeated many top lightweights following his promotional debut in 2007. Fighters he defeated included Frankie Edgar, Jim Miller, Kenny Florian, and Nate Diaz. His impressive wins led many to believe that he could be the one to dethrone Penn and become lightweight champion. Unfortunately for Maynard, he didn’t get that opportunity as Edgar defeated Penn in the championship and rematch bouts.
2012 would have been a realistic timeframe for the Penn vs. Maynard matchup. ‘The Bully’ had come off back-to-back title bouts against Edgar, which were classics. Meanwhile, ‘The Prodigy’ was coming off a loss to Nick Diaz in a welterweight title-eliminator. Rather than fighting Rory MacDonald, Penn could’ve returned to lightweight for a bout with Maynard.
#4) UFC Hall of Famer Randy Couture
Dana White made an interesting revelation during his post-event press conference following UFC 227. He recalled a past conversation and mentioned that B.J. Penn refused to fight Randy Couture when asked to face him at heavyweight.
The thought of Penn fighting Couture wouldn’t have been out of the ordinary. In fact, ‘The Prodigy’ has competed against much larger opponents while competing in K-1. He fought Rodrigo Gracie at middleweight, a 225-lb Lyoto Machida in an openweight bout, and Renzo Gracie at light heavyweight.
“B.J. Penn is old school from the old mold and B.J. literally wanted to fight everybody that was out there and I respect that, but there are limits." – Dana White to the media during UFC 227 post-event press conference
Penn vs. Couture would have been a spectacle had the promotion booked it. Perhaps if it wasn’t a heavyweight bout, light heavyweight would have been more realistic. ‘The Prodigy’ would’ve been the underdog and fans would've definitely been interest in watching these two legends compete in the cage.
#3) Rematch with Jon Fitch
It's surprising that the UFC never booked an immediate rematch between B.J. Penn and Jon Fitch. Since welterweight bouts were on the horizon at the time, it would have been logical to book a rematch.
Their first encounter saw them both fight to a draw with the judges scoring the bout 28-29, 29-28, and 28-28. It was a technical battle between two elite fighters. Based on what transpired in the first and second rounds, Penn looked to the edge going into the final round. But, Fitch’s strong performance in the final round was enough to earn the draw. The round saw Fitch maintain ground control and he didn’t allow the former champion any opportunity to return to the standup.
‘The Prodigy’ was competing in his second welterweight bout since his 21-second knockout win over former champion Matt Hughes. Another win could have made a strong case for ‘The Prodigy’ earning a trilogy bout with Georges St-Pierre.
#2) UFC Hall of Famer Urijah Faber
A bout with Urijah Faber could have generated plenty of interest for the UFC. The ideal timeframe for the promotion to book the bout was when they were both champions of their respective weight classes.
Despite a superfight not taking place in 2008 when they were champions, it was still a possibility years later. Based on their career trajectory, 2014 would have also been the logical choice. The promotion had ‘The Prodigy’ and Frankie Edgar serving as coaches on TUF season 19 that year. It didn’t really make sense at the time, considering the fact that ‘The Answer’ had already beaten Penn twice.
‘The California Kid’ would have been a better option to coach opposite ‘The Prodigy’ because they hadn’t fought before. They could’ve coached at TUF season 19 and then fought at the finale. Their popularity and legacy in the sport could have brought a lot of attention to the event. In Penn’s case, perhaps the bout is one that he could have been content with retiring after.
#1) Former UFC title challenger Jake Shields
B.J. Penn vs. Jake Shields was a huge missed opportunity for the UFC. Both were accomplished fighters in multiple weight-divisions throughout their careers and it could have been an intriguing bout.
Shields debuted with a lot of promise following his tenure at Strikeforce. The former Strikeforce middleweight champion was riding an impressive 14-fight winning streak. Some of his wins were against Carlos Condit, Paul Daley, Robbie Lawler, and Dan Henderson.
His octagon debut was fairly successful as he defeated Martin Kampmann via split decision. Shields’ winning streak came to an end when he was defeated by then welterweight champion Georges St-Pierre at the promotion’s first event in Toronto, Canada.
The bout could have been realistic in 2012. Shields fought Jake Ellenberger in September 2011, while ‘The Prodigy’ fought Nick Diaz in October 2011. They both lost their respective bouts. So, Penn vs. Shields would have made sense as they both needed a win to remain in the title picture.
