6. BJ Penn (2004-06)
Recently Dana White referred to BJ Penn as the UFC’s most underachieving fighter. Its actually not hard to see why that is. “the Prodigy” was instantly good at Brazilian Jiu Jitsu, and became the best in the world at it after training for only a few years. The problem with people who are instantly good at things is they often think they don’t have to keep getting better. BJ Penn never improved throughout his career, which is why by the time he hit just 32 years old the game passed him by, everyone else got better but he had stayed the same.
BJ finally won a championship in the UFC on his 3rd attempt, when he defeated Matt Hughes for the Welterweight Championship at UFC 46. To thank the company for giving him 3 shots at a championship (lost to Pulver at UFC 35, drew with Uno at UFC 41) Penn announced he was leaving the company in 2004 because there was nobody left in the UFC to challenge him. He signed a deal to fight exclusively for K-1, and the UFC stripped him of the title. Penn tried to file a court order to prevent the UFC from declaring a new Welterweight Champion, but it was denied. Considering how Penn has treated the company in the past, its really no surprise that White is quick to be critical of him.
In 2006 Penn re-signed with the UFC and promptly lost his first two fights before dropping to lightweight.