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5 B.J. Penn fights that should've but didn't happen in the UFC

Hall of Famer and former two-division champion 'The Prodigy' B.J. Penn
Hall of Famer and former two-division champion 'The Prodigy' B.J. Penn

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

Apr2.2008

Gray Maynard hands Frankie Edgar the first loss of his professional career.

This was the beginning of one of the most competitive rivalries in UFC history. https://t.co/VaU22YAVcM

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.


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