It was recently revealed by UFC President Dana White that MMA legend Dan Henderson will get his choice between fighting the winner of Anderson Silva vs. Chael Sonnen or Jon Jones vs. Rashad Evans. This unique luxury rarely gets extended to fighters in the UFC–not even to most champs–but the “ugly” 41-year-old Henderson is a special case with a lot of leverage when it comes to dealing with his “fat” old friend Dana. This shouldn’t come to a surprise considering Henderson’s rather candid relationship with White and more importantly, coming off a fight of the year contest against Mauricio “Shogun” Rua–along with a slew of career accomplishments unmatched by most guys his junior.

That leaves the former champion with a welcomed dilemma of choosing between fighting for two belts once he steps back into the Octagon. Now that he is in such a sought after position–wedged between two hunks of gold–which fight makes more sense for Henderson at this point in his storied career?

Historically speaking, the middleweight division has been physically and somewhat less kind to Henderson compared to light heavyweight. After Pride FC was dissolved by the UFC, Henderson has fought twice for middleweight gold and lost. His first effort was against Anderson Silva in a unification title fight back at UFC 82 in 2008 that he lost by a second-round rear-naked choke and his last effort for 185-pound glory was dashed by a decision loss to then Strikeforce champ Jake Shields.

Granted, Henderson’s entire time at 185 pounds, post Pride days, was not a complete loss. Prior to fighting Shields, Rousimar Palhares succumbed to a Hendo decision victory at UFC 88 and Michael Bisping found himself on the wrong end of possibly the most vicious knockout up to that point at UFC 100. That overhand right landed with such explosive force pundits and fans were compelled to give Hendo’s most dangerous strike a name: the H-Bomb.

Unfortunately, the Shields fight marked a noticeable change in the aging fighter. Henderson’s cardio tank ran mostly on fumes throughout the entirety of the fight–mainly due to pre-fight complications cutting weight and possibly being under the weather. It’s no secret cutting to middleweight is not something Henderson prefers doing, especially as he gets older. As fighters start to age, wear and tear makes training and cutting more difficult and as testosterone levels start to wane, it becomes physically easier on the body to compete at a heavier weight opposed to vigorously cutting down to lighter weights.

In addition to the physical obstacles of fighting at 185 in the UFC at the tender age of 41, there is the issue of potential opponent. Hendo has already made it very clear that he does not want to fight Chael Sonnen, his former Team Quest training partner. Assuming Sonnen repeats history in some fashion during his rematch with the champ, that would leave Henderson with a rematch of his own–a stylistic nightmare with a lengthier, quicker and more elusive fighter. Anderson Silva’s range, striking and sprawl are all too complete and dynamic, making Hendo’s simplistic, yet predictable, one hitter-quitter H-Bomb inadequate.

In fact, Henderson’s chances of beating light heavyweight champion Jon Jones is equally daunting. Though, he would be a lesser underdog against Rashad Evans. In reality, there is a good chance Vegas would have Hendo has an underdog against all four potential opponents, but he would certainly have a better shot of winning at 205 pounds (against Evans). Plus, all of his rejuvenated success over the last year has been in the heavier weight classes.

Prior to his epic, five-round battle of attrition with top-ranked Rua, Hendo’s three previous bouts were convincing wins that proved he felt and fought more effectively coming into the cage heavier than middleweight. He KO’d Renato Sobral in the first round of a Strikeforce title eliminator bout, TKO’d Rafael Cavalcante for the Strikeforce light heavyweight strap and then followed that victory up by taking out legendary Fedor Emelianenko last summer in the first round of their highly anticipated match-up.

Despite trying to stay one step ahead of Father Time, the now No.1 contender has proven that light heavyweight is the division Henderson is better suited to reach his potential to win a UFC belt, an accomplishment that has eluded one of the sport’s most revered competitors.

Smart money says there is no good reason to tackle a fighter like Silva at 185 pounds if a fight with the light heavyweight champion is on the table. Plus, the Silva vs. Sonnen rematch is not until June and obviously Henderson’s no spring chicken. At 41, there should be a sense of urgency that should persuade Hendo to avoid a longer layoff than necessary. Realistically, whichever path he picks will signify a precursor to retirement. It’s very unlikely he’ll have another run at UFC gold should he lose either title fight.

There is a lot hanging on his decision and it should be made based on what increases Henderson’s chances of winning.

Photo: Dan Henderson (Sherdog)

This piece was authored by Joe Schafer. You can find Joe on Twitter: @joeschafer84

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