Despite all the punishment he's taken during his magnificent career, in which he's won world championships in three weight divisions and seemingly already has the curators clearing space for him in the International Boxing Hall of Fame, Miguel Cotto has proven himself to be a very astute businessman.
Cotto will challenge Sergio Martinez on Saturday at Madison Square Garden in New York for the WBC middleweight title. If he defeats Martinez, the reigning champion, Cotto will become the first Puerto Rican-born boxer to win world titles in four weight classes.
He already has world title belts at super lightweight, welterweight and super welterweight in his trophy case. A victory over Martinez would be massive, but it could also be setting himself up for an epic follow-up.
Consider this: Floyd Mayweather, who defeated Cotto in 2012, holds both the WBC welterweight and super welterweight belts. No boxer has held three major weight class championships at the same time since Henry Armstrong held the featherweight, lightweight and welterweight titles in 1938.
Mayweather has yet to announce his opponent for a Sept. 13 bout, and it would be difficult for Cotto to fight in another major event in 97 days. But there is nothing set in stone that would force Mayweather to fight on Sept. 13, especially if he could pull off something as historic as holding a title in three weight classes simultaneously.
It's all possible – unlikely, yes, but at least possible – because of the brilliant way Cotto has handled the latter part of his career. The fact that scenario is even remotely possible speaks to the shrewd manner in which Cotto has positioned himself over the last several years.
Cotto spent most of his career with Top Rank, repeatedly referring to it throughout the years as "my company." He was recruited out of the 2000 Olympics by Top Rank president Todd duBoef, and the two maintain a close friendship to this day.
In late January 2012, when the free agent Cotto opted to accept an offer to fight Mayweather, the first person he notified was duBoef.
Mayweather, of course, doesn't do business with Top Rank and so signing a deal to fight him meant leaving the only promotional company Cotto had ever known.
The split was amicable because Cotto had kept duBoef in the loop throughout the decision-making process. Perhaps he did it because of their friendship, but it was also wise for business reasons. If Cotto had beaten Mayweather, he'd have been obligated to give him a rematch. A win over Mayweather would have been an all-timer and Cotto would also have created massive opportunities for himself.
He would have been a viable opponent for a rematch with the Top Rank-promoted Manny Pacquiao as well as a fight with Golden Boy-promoted Canelo Alvarez.
Cotto gave Mayweather one of his toughest fights, but lost a unanimous decision. He opted for a bout with the then-unbeaten Austin Trout as a comeback match, attempting to leverage his popularity in New York, but Trout's style was totally wrong for him and Cotto wasn't himself in a one-sided loss.
Still, Top Rank remained interested in promoting Cotto again, and for good reason. It had a slew of potential opponents for Cotto and a rematch with Pacquiao remained on the table.
It says a lot about what Cotto meant to the company that many of its employees were giddy when Cotto re-signed with Top Rank to face Delvin Rodriguez last year.
Rodriguez is little more than a journeyman, but after back-to-back losses, Cotto not only needed to get back on the winning track, but he needed a veteran trainer to overhaul his game.
He hired Freddie Roach, who works closely with Top Rank, and Cotto seemed like his old self in a dominant victory over Rodriguez.
It's good to be skeptical of that win, because Rodriguez isn't remotely in Cotto's class, and a win over Rodriguez hardly means he's ready to compete on even terms with someone like Martinez.
But Cotto used that win over Rodriguez to vault himself into a major bout with Martinez that has intense fan and media interest. If Cotto puts up a good performance, he opens the door for all manner of big fights.
If he wins, he could potentially face Alvarez if Alvarez gets past Erislandy Lara in their July 12 bout in Las Vegas. A Cotto-Canelo fight is one of the more entertaining scraps that could be made.
A second bout with Pacquiao would be interesting, even though Pacquiao stopped Cotto in the 12th round in 2009. Top Rank CEO Bob Arum said he will offer Juan Manuel Marquez the first crack at Pacquiao, but Marquez is going to drive a hard bargain and is no sure thing to accept.
Assuming he could make welterweight again, Cotto would also set himself up for fights with Timothy Bradley, Amir Khan, Marcos Maidana, Shawn Porter and Keith Thurman if he looks decent against Martinez.
Cotto's stature in the business remains enormous, nearly 14 years after his career began. An email from a publicist to reporters covering Saturday's fight was telling about the manner in which the industry regards Cotto.
"The press turnout for this fight is enormous," the publicist wrote, using yellow to highlight the paragraph to call attention to it. "Therefore, we have very limited seating."
Nobody cares about where reporters get to sit, but the point is that even in the home stretch of his career, Cotto can still pack them in.
Very few fighters over the past 25 years have come close to handling the stretch run the way Cotto has.
Cotto isn't one for attention and he's never met an interview he was eager to do. He'd far prefer to go to the gym, train and head home than deal with reporters the way stars of his caliber must do. But Cotto is the consummate professional and handles all of his business in a first-class manner.
If he beats Martinez and Mayweather shows the slightest interest in facing him, it would mean an enormous payday for Cotto. By signing short-term deals and keeping his options open, Cotto has given himself the best chance to make the most money and compete in the most important fights.
Cotto has mainted good relationships with promoters on all sides, so he's positioned himself perfectly for whatever happens.
If he wins the fight on Saturday, he's got to make at least two more massive paychecks. And in a sport such as boxing, where one's very life is at risk every second of every round, those massive paychecks are extremely alluring.
Boxing is often a strange and confounding business. There is no barrier to entry and anyone with a couple of bucks in the bank can become a promoter or a manager. Having a good relationship with someone who turns into a top boxer can make a man a powerbroker in the sport almost overnight.
But Cotto and his team have managed the process nearly perfectly. He's positioned himself expertly, putting himself in the best fights for the biggest money while maintaining his reputation as a fan-friendly fighter.
Newcomers could do a lot worse than to study the way Cotto has tread boxing's shark-infested waters.