Rickson Gracie reportedly left a sizeable offer on the table. | Photo: Marcelo Alonso/Sherdog.com
9. Rickson Gracie vs. Kazushi Sakuraba
Sakuraba made his name as “The Gracie Hunter,” and he more than earned that reputation by finishing Royler Gracie with a kimura, defeating Royce in a grueling 90-minute match, taking out Renzo with another kimura and beating Ryan Gracie by decision, all in 1999 or 2000. Sakuraba was a huge draw for the nascent Pride Fighting Championships promotion, and his rivalry with the Gracies was a substantial part of his appeal.
A match between Sakuraba and Rickson, the family’s toughest fighter, would obviously have been huge business. Pride’s matchmakers reportedly offered Gracie $5 million to take the fight, and he might well have accepted it but for the untimely death of his son, Rockson, in January 2001. Gracie retired from MMA competition after the tragedy, and the matchup with Sakuraba never came to fruition.
Number 8 » Hamstrung