"I almost beat Machida which makes me the number one contender, right?"

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June 29, 2001.
 
On that date, the UFC was experiencing their third show under Zuffa management, Fedor was a full year away from making his Pride debut, and Eminem was still relevant to the music scene.
 
That was also the last time Tito Ortiz finished an opponent not named Ken Shamrock.
 
The main-event of UFC 32: Showdown in the Meadowlands, featured then light heavyweight champion Tito Ortiz overwhelming Elvis Sinosic with punches and elbows on his way to a quick first-round TKO victory. All of his victories since then -- save for Shamrock -- have come via split or unanimous decision. Back at UFC 59, it appeared that Ortiz was on his way to another first-round TKO victory over Forrest Griffin as he looked like the Tito of old, dropping vintage elbows on Forrest before Griffin rallied back in the second and third rounds. Many fans (and one judge) felt that Forrest actually won that fight -- and while it officially goes down as a Tito victory, that night proved to elevate Griffin's career more than Ortiz's.
 
After dominating Shamrock for the second and third time, Ortiz went on to lose his rematch to Chuck Liddell as he couldn't successfully work his takedowns and he looked very uncomfortable during the stand-up exchanges.  At the UFC 73 weigh-ins, Ortiz towered over Rashad Evans and most felt that he would be able to dominate his smaller opponent with his wrestling and size advantage. Ortiz's much vaunted conditioning appeared to fail him as he gassed in the third round and was penalized a point for grabbing the fence on his way to an unsatisfying draw in a fight he should have won. One also can't forget that he was dropped by an overblown middleweight in Patrick Cote during their fight at UFC 50. Ortiz looked unimpressive in collecting another decision victory in what was a very dull affair.
 
Although Ortiz almost pulled a rabbit out of his hat with his near-triangle/armbar on Lyoto Machida at UFC 84, he has always relied too heavily on his wrestling and takedowns.  When those weapons fail him, he quickly loses confidence as he doesn't have much to fall back on.  Despite what would have been a miraculous submission over Machida, Ortiz has shown almost no evolution as a mixed martial artist since he debuted over 12 years ago. 
 
As the 2009 Dana White Reconciliation Tour stopped to "welcome back" the "Huntington Beach Bad Boy" this past week; rumors abound that Tito Ortiz will soon be returning to the only MMA organization that he has ever fought for. While Ortiz still holds a great deal of fanfare --his bout with Chuck Liddell still holds the UFC record for live gates-- the question remains: Will Ortiz be in a position to contend for the title or nothing more than a highly-paid gatekeeper. 

Thanks to Tito's proclivity for self-promotion, there are a great number of highly-anticipated rematches including Forrest Griffin, Rashad Evans, and perhaps even Lyoto Machida. Of course Ortiz could do big business in fights against Rampage Jackson, Jon Jones and even Mark Coleman. 
 
The question is not just: "Can Tito win?"  The question is: "Can Tito finish?"
 
As Rashad Evans and Anderson Silva have shown, finishing your opponent in spectacular fashion is the best way to become a viable contender and position yourself for a title shot.  Lay-and-pray decisions and anemic striking don't do a whole lot to impress fans or the UFC brass. 
 
Ortiz has a well-documented history of problems with his back, which he now claims to be at 100% and is relatively young at 34 years old.  Can Tito focus and get himself into the type of shape needed to experience Couture-like levels of career-longevity? Does he still have the ability to fight and succeed at the highest level against multi-faceted and ever-evolving opponents? 
 
Hopefully soon we will get answers to all the questions.