5. Dan Henderson
Pride’s only two-division champion, Henderson’s legacy in the promotion mirrors his career as a whole: He had some exceptional highs as well as considerable lows. As I wrote in his entry for Sherdog's Top 10 Middleweights, where he also finished fifth, he has perhaps the strangest, most perplexing and unique career in the history of MMA. It all comes down to Henderson's unique style. Despite being a former Olympic wrestler, he rarely used wrestling to win fights and could be taken down and controlled himself. Instead, he relied on his boxing, predicated on one of the most devastating right crosses in MMA history, plus an iron chin. Either Henderson caught his opponent, and it was spectacular, or he didn't, and it was disappointing. From a more negative perspective, Henderson was 13-5 in Pride, though I think it should have been 11-7. Henderson won a robbery against “Ninja” Rua and at least an undeserving decision against Murilo Bustamante, the same two snake-bitten fighters who lost split decision robberies to No. 9 entry “Rampage” Jackson. Henderson was also dominated by Ricardo Arona, who took him down at will, lost a clear decision to a prime Wanderlei Silva, was armbarred by both Nogueira brothers, and was clearly beaten by good but unexceptional fighter Kazuo Misaki, an unfathomably bad loss for anyone on this list, especially one who cracked the Top 5. But consider his successes! Knocking out Bustamante, in my opinion the most underrated fighter in MMA history and top 10-15 pound-for-pound all-time, in less than a minute in their first fight, knockouts of solid foes in Ryo Chonan, a prime Akihiro Gono, the larger Kazuhiro Nakamura and Renzo Gracie, a dominant decision over Vitor Belfort, and his crowning achievement, a knockout of Wanderlei Silva in their rematch in his final Pride outing, becoming the final Pride middleweight champion. Truly a career of contrasts in Pride, just like his career overall. While I had him lower, he is still a worthy inclusion on this list.
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