#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.
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‘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.