Former Pride FC middleweight (205 pounds) and welterweight (183 pounds) champion was supposed to be the man to give UFC Middleweight Champion everything he could handle.
And for about five minutes during their championship fight at UFC 82: "Pride of a Champion" back in March 2008, it appeared that the Greco Roman Olympic-level wrestler did indeed have the Brazilian's number.
He took down "The Spider," put him on his back, smothered his airway and landed a few solid strikes to do what no other man was seemingly able to do up until that point inside the Octagon: win a round against the dominant champion.
However, the momentum would quickly shift to start the second, with Silva stunning Henderson midway through it and using the opportunity to take his back. It was only a matter of time before the Nogueira-trained Brazilian jiu-jitsu black belt was able to sink in a fight-ending rear naked choke.
Silva has since gone on to win eight consecutive fights. He most recently mopped the floor with Yushin Okami at UFC 134: "Rio" before a raucous crowd in Brazil. Henderson, meanwhile, has won six of his last seven, stopping Fedor Emelianenko in a thrilling "super fight" earlier this year under the Strikeforce banner.
Henderson, who also happens to be the Strikeforce light heavy weight champion, is now a free agent. It is widely believed that he will return to the Ultimate Fighting Championship (UFC) now that his current deal is done.
It's not necessarily a matter of if, but when. In addition, at what weight class.
Prior to the major announcement that UFC Heavyweight Champion Cain Velasquez would put his title on the line against number one division contender, Junior dos Santos, on the first-ever UFC on Fox Fight Night scheduled for Nov. 12, 2011, speculation swirled that Henderson could possibly rematch Silva in primetime.
Henderson, through his manager, admitted that the chance to fight Silva "would probably be the only fight he'd consider" at 185 pounds. Who could blame him?
As mentioned earlier, he's the Strikeforce 205-pound champion, which makes a match up with the UFC light heavyweight champion, also a very juicy option. Henderson, 41, has also been on a roll competing north of middleweight, finishing three straight fights in impressive fashion.
His last fight at middleweight, against Strikeforce middleweight champion Jake Shields, was an absolute disaster after Henderson punched himself out in the first round of their 25-minute fight.
It's an interesting position that is actually very familiar for Henderson. Back in 2007, shortly after the Zuffa purchase of Pride FC, UFC rolled out the red carpet for "Hendo" with back-to-back instant title shots.
He dropped a close five-round unanimous decision to 205-pound champion Quinton Jackson in his re-debut for the promotion and then the second round submission loss to Silva transpired six months later.
At this advanced stage of his career, and with Silva seemingly without any clear-cut contenders standing in his path sans Chael Sonnen, it is the ideal time to run it back. Sonnen is busy with Brian Stann, while Henderson and Silva are healthy, ready and currently opponent-less.
Henderson has the skill set to defeat Silva. He has the experience. He has the mental ability. He just needs a new contract, and the offer, to give it one more shot, literally, before it's too late.
Timing is everything.