By Jake Donovan

Miguel Cotto couldn’t ask for a better weekend to attempt to make history for his native Puerto Rico.

A win over World middleweight king Sergio Martinez will make him the first ever from the island to have won major titles in four weight classes, with the two colliding this Saturday at Madison Square Garden. The event has long ago sold out, a reminder of Cotto’s longtime drawing power at the venue, particularly on this time of the year, when his prizefight lands on the eve of the annual Puerto Rican Day Parade in New York City.

This year’s offering comes in the midst of a perfect storm, with all eyes on three generations of Puerto Rican boxing culture.

Hours before Cotto steps into the ring, the Garden will get a good look at Felix Verdejo, the outstanding lightweight prospect who represented Puerto Rico in the 2012 Olympics. One day later, one of the island’s favorite sons, Felix Trinidad will be honored alongside Oscar de la Hoya and Joe Calzaghe as the three retired modern-day boxers gaining enshrinement in the International Boxing Hall of Fame.

The series of events comes right on time for a nation whose boxing culture is in dire need of a shot in the arm.

From the moment Rocky Martinez lost his 130 lb. title to Mikey Garcia last November, Puerto Rico found itself without a major titlist for the first time in decades. The closest the island can claim to a champion of its own is Danny Garcia, the king of all 140 lb. fighters who is of Puerto Rican descent but born and raised in Philadelphia.

At the time of Martinez’ knockout loss, Cotto was moving towards discussion for a shot at the middleweight crown. The former three division champion was a month removed from a comeback win, stopping Delvin Rodriguez in three rounds last October to halt a two-fight losing streak. The 22 months he went between wins was the longest of an otherwise unforgettable career that – surprisingly from a popularity standpoint – put him no worse than alongside his predecessor, Felix ‘Tito’ Trinidad.

Boxing culture runs deep in Puerto Rico, who’ve celebrated their heroes all the way back to when Sixto Escobar claimed the World bantamweight crown in 1934 to become his nation’s first ever world champion.

From there, the tiny but proud island has watched the likes of Wilfred Benitez become the youngest fighter ever to win a world championship, upending 140 lb. king Antonio Cervantes at just 17 years of age. By the time he was 21, Benitez claimed titles in three divisions and was already being discussed among the best in boxing history, as well as the next great fighter to come out of Puerto Rico since Carlos Ortiz established himself as one of the best lightweights of all time more than a decade prior.

The same show that saw Benitez’ last ever title fight – conceding his 154 lb title to Thomas Hearns on Dec. 3, 1982 – also bore witness to the final night of the incredible 122 lb. title reign enjoyed by Wilfredo Gomez. His 14th round knockout of Lupe Pintor capped a historic run, with his 17 consecutive title defenses remaining a divisional record. Each and every title defense came by way of knockout, a record for any division and one that may never be broken.

Benitez and Gomez both claimed championships in three weight classes. So, too did Trinidad, Wilfredo Vazquez and the late Hector ‘Macho’ Camacho.

None ever came close to winning a major title in a fourth weight division. Benitez suffered losses on the non-title level as a fish out of water in the middleweight division. Gomez never made a run at lightweight following his 130 lb. title reign-ending knockout loss to Alfredo Layne in 1986. 

Vazquez topped out at featherweight, scoring a miraculous knockout of lineal champ Eloy Rojas in the 11th round of their May '96 title fight for his third championship. Fittingly, the feat came on the undercard of a show headlined by Trinidad, who two years prior was - oddly enough - the first to deny Camacho a shot at Boricua history.

There was no love lost between the two when Trinidad soundly outpointed his bitter in-country rival in their Jan. ’94 welterweight title fight. Camacho had claimed belts at 126, 130 and 135. Like Benitez and Gomez before him, he was considered a prodigious talent at a young age, but met his match as he climbed the scales, as Trinidad was dominant to the point of Camacho holding on for dear life down the stretch. 

Camacho also dropped a landslide decision to Oscar de la Hoya in his second failed welterweight title bid in 1997.

The all-Puerto Rico showdown with Camacho was the first of three big wins in a memorable 1994 campaign for Trinidad. Knockout wins over then-unbeaten contenders Yory Boy Campas and Oba Carr solidified his stance as one of the best welterweights in the world. His reign ended in bittersweet fashion – a win over de la Hoya in Sept. ’99, though in a fight where few believed he actually deserved the majority decision awarded to him.

The fight itself propelled his star power, serving at the time as the largest-selling non-heavyweight pay-per-view event in boxing history. His popularity soared from there. A pair of wins over David Reid and Fernando Vargas established his presence as the king of all 154 lb. fighters, and also good enough to land Fighter of the Year honors in 2000, the final year of the 20th century and 2nd millennium.

Cotto was three fights into his pro career by the time Trinidad sought to become a three-division champ. The atmosphere at Madison Square Garden for his May ‘01 middleweight title challenge of William Joppy went virtually unmatched for years. Trinidad delivered, scoring a 5th round win to join Benitez, Gomez and Camacho as triple-division title winners.

His popularity was at – and remained – at an all-time high, even after suffering the first loss of his career in humbling fashion. Trinidad was made to look amateurish as he was manhandled by Bernard Hopkins in their Sept. ’01 undisputed middleweight championship, the last time the wildly popular Boricua would enter the ring as champion, and also the first night the phrase “Hall of Fame fighter” accompanied Hopkins’ career.

Trinidad had already established his credentials by then, enough to where he earned Hall of Fame enshrinement in his first year of eligibility.

While Cotto will be knee deep in Fight Week festivities in New York City, Trinidad will be four hours north, front and center for all that comes with Hall of Fame weekend in Canastota.

"This is a great honor for me, my father, my family and my whole team," Trinidad says of being recognized in such light. "This is the biggest triumph of my career."

Where Trinidad ranks among the best in Puerto Rico’s boxing history is open for debate. So too is Cotto’s place among the island’s greatest fighters. A win over Martinez this weekend would undoubtedly cast new light on such conversations, with such a feat meaning that much more coming in a venue that Cotto helped reestablish as a boxing landmark

“It is a personal matter,” Cotto (38-4, 31KO) says of going after the middleweight championship. “(It’s) a personal achievement that I want to win and I am working for it on June 7. It doesn’t mean that I am going to be better than Wilfredo Gomez, better than Félix Trinidad, better than all of the great champions that Puerto Rico has produced, but for me, Miguel, it will be the greatest accomplishment of my career.”

Win or lose, Cotto can leave the ring knowing the future of the island for which he has for more than a decade served as the face of its boxing culture is in capable hands.

Verdejo (12-0, 9KO) has twice performed in MSG’s The Theatre, but plays the Garden’s main room for the first time in his career. Cotto was already a well-established 140 lb. titlist by the time he debuted at the venue in 2005, a move that promoter Top Rank believed was necessary in tying in boxing to the Puerto Rican Day Parade.

“I think the history of the Puerto Rican influence and how it works with boxing goes way back,” Top Rank President Todd duBoef explains in the marketing strategy. “The thinking was in Las Vegas we had seen the rise of both Puerto Rican and Mexican Independence Day holidays and we felt that if we could link something up with the Puerto Rican Day Parade, which is their celebration, it could be something magical, and who better to do it with than Miguel. 

“I could say this, that the first event there was some education. We had to give consumers – they weren’t used to the walk-ups and the buying of the tickets I think previously at The Garden – for some of the Tito Trinidad fights they had been throwing tickets around on the town. But over time with Miguel we have set up an incredible property and a great celebration for all Puerto Ricans to come together. And Miguel has been terrific in leading the way for many more fighters to come.”

Cotto is 7-1 overall at Madison Square Garden. Four of the wins have come on the eve of the Puerto Rican Day Parade celebration, along with a fifth in 2010 when Cotto brought boxing back to Yankee Stadium, if only for a night. Mohammad Abdullaev, Paul Malignaggi, Zab Judah, Joshua Clottey and Yuri Foreman comprise of the list of fighters brave enough to stand opposite corner for a fight landing on the most significant weekend of the year for Puerto Rico culture as celebrated in New York.

Verdejo figures to be the next to carry the torch for la Isla del Encanto, and is being given the full star treatment even as a fighter appearing deep on the undercard. Thanks to Cotto’s influence – both as one of the sport’s biggest stars and as an active promoter – fights from the non-televised portion of the undercard—including Verdejo, fellow unbeaten prospect Jose Pedraza and debutant Jantony Ortiz—will appear on WAPA-TV, a Spanish-language network headquartered in San Juan.

“We are very happy to present these bouts, which will feature some of the top prospects from Puerto Rico,” Cotto said. “This historic telecast will be enjoyed by all Puerto Rican fans.” 

Among the Puerto Rican fans planning to tune in to watch its future star, is none other than one of its biggest ever stars from the past.

“In Puerto Rico people are talking a lot about him,” Trinidad said of Verdejo in a recent interview with Puerto Rico’s primary print publication El Vocero. “He is a good kid and very dedicated to boxing. Felix Verdejo has all the potential to become the next 'Tito' Trinidad. He has everything. He is tall and he has a great record.

“He has a record a lot alike mine when I started boxing - an impressive record. I hope he stays undefeated; he has all the tools to become a solid world champion.”

Of course, with such lofty praise from a past great and promotional support from the island’s current favorite son, the bar is seriously raised for Verdejo, who just turned 21 in mid-May.

“"I'm very happy and excited. Hearing those words from my childhood idol, Felix 'Tito' Trinidad, is something pretty big for me,” Verdejo admits. “He gave Puerto Rico a lot of glory and without him knowing, he taught us how to be humble.

“All that good advice he gave me, I will always take that with me. He was the one who motivated me to become a boxer and is a big honor to hear him speak like that about me. This motivates me to work even harder to reach all my goals.”

If present forecast plays out, there stands a great chance that Verdejo’s name will be intimately involved in any given discussion of where to rank the best fighters to come from Puerto Rico.

But then if present forecast plays out, Cotto faces a major uphill challenge this weekend.

The 33-year old is more than a 2-1 underdog to rewrite history for Puerto Rico. The bout is his first as a middleweight, having never weighed above the 154 lb. super welterweight limit for any given prize fight through 13 years as a pro.

Despite the odds, Cotto remains the overwhelming sentimental favorite in Saturday’s pay-per-view headliner. A win should propel his career to similar heights in which Trinidad’s rabid fan base spoke of its hero.

“I am just waking up every day trying to do my best in preparation so I am at my best for every opportunity that I have to fight,” Cotto says as humbly as ever, even with his popularity at an all-time high. “I don’t want to be named, myself, as one of the elite boxers of Puerto Rico – that’s for the fans and for the people that know about boxing.

“I just want to do my job the best I can and I am going to do that the rest of my career.”

A career that – win, lose or draw this weekend – will forever remain an integral part of Puerto Rico’s rich boxing history.

Jake Donovan is the Managing Editor of BoxingScene.com, as well as a member of Transnational Boxing Ratings Board and the Boxing Writers Association of America. Twitter: @JakeNDaBox