Ranking the modern history of Cinco de Mayo weekend boxing main events

Tonight, we were supposed to be watching Canelo Alvarez, probably against Billy Joe Saunders, as boxing’s modern history of big fights on Cinco de Mayo weekend (this is an adjustable time frame, really) was set to continue.

Would Canelo-Saunders have been a good fight? Maybe. It’s a big fight because it involves Canelo; any fight with him at this point is a Big Fight. Both are tactical guys, really, but they also do both have some fire and aren’t afraid to mix it up. It could have been a snoozer, or it could have been sneaky good. I was about 65/35 on that, leaning toward snoozer, but not discounting completely the idea that it might be a pretty good fight in the end.

But of course, we instead have nothing. Boxing has been shut down, basically, since Mar. 13 — that was the last time we had a live fight to cover, an empty room ShoBox from Minnesota. To think of how we took these things for granted. My kingdom for an Erislandy Lara vs Canelo’s Brother FOX main event right now.

As for Cinco De Mayo weekend, this is still a relatively new thing in boxing, really starting in 2003 as something consistent, meaning we’ve had 17 Big Fight Main Events from this tradition.

There’s not much to do, so let’s rank ‘em! And obviously this is all just my opinion; one person’s highly engaging chess match is another person’s “need to brew some coffee in round eight,” after all.

17) Canelo Alvarez vs Julio Cesar Chavez Jr, 2017

The honor of the Worst Fight on this list goes to this 2017 HBO pay-per-view main event. Oscar De La Hoya started the tradition, kind of by accident, and passed the torch to Floyd Mayweather and Manny Pacquiao after it had become a whole thing. When those two faded/retired/became Senators/whatever, the torch was then passed to Canelo Alvarez, the first fighter born in Mexico to become the A-side of these Cinco De Mayo battles.

Canelo’s run on the weekend didn’t exactly start triumphantly in some ways, between the Amir Khan fight in 2016 and then this one. I mean, for him, it was fine; he made a lot of money and this fight sold pretty well, as he faced another Mexican star in Chavez. Trouble is, Chavez isn’t very good and barely showed up for this fight at all. Basically, he made the catchweight and then got in the ring. His effort ceased there, as Alvarez dominated an extremely dull fight where his opponent provided almost no resistance whatsoever, other than defending himself enough to not get knocked out at some point.

16) Oscar De La Hoya vs Steve Forbes, 2008

This 2008 fight was De La Hoya’s return to HBO airwaves after years as a PPV-only star, meant as a “gift” to fight fans; that’s how it was marketed, as if we were privileged to watch De La Hoya put on a glorified sparring session for our HBO subscription money. “We’re not even going to charge you another 50 or 60 dollars,” the smiling faces at HBO said to us repeatedly.

Forbes was a good fighter, but he wasn’t special, and he had a pretty established level. He’d lost back-to-back fights to Grady Brewer and Demetrius Hopkins not long before this matchup. He was an ideal sparring partner, though, as De La Hoya was preparing for a planned rematch with Floyd Mayweather, this time at 147 pounds instead of 154. This 150-pound catchweight bout was meant to get Oscar ready for that drop down in weight, staying active and getting a W after his loss to Mayweather a year prior.

Oscar won a totally forgettable decision over 12 rounds where he never really pressed much, and Forbes had nothing that was going to be a real threat to De La Hoya. The Mayweather rematch never happened, as Floyd “retired” again instead, but Oscar kept the ill-fated idea to go back down to 147, facing Manny Pacquiao instead in what turned out to be De La Hoya’s final bout in Dec. 2008.

15) Manny Pacquiao vs Shane Mosley, 2011

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This fight wound up being most notable for some of the political stuff surrounding it, and for the hilarious performance of CBS Sports personality James Brown, who served as the host for the event.

James Brown and CBS were involved because Pacquiao promoter Bob Arum and HBO got into a bit of a pissing contest, so Arum took Pacquiao to Showtime, whose boxing brand had been suffering a lack of star power in recent years. Showtime and CBS were eager to jump into the Pacquiao business, and they accepted a fight against Mosley, who had looked lousy in his previous fight, an ugly draw with Sergio Mora. This fight also came a year after Mosley lost to Floyd Mayweather, and we’ll get into that one in a moment here.

Pacquiao-Mosley was a brutally non-competitive fight, with Mosley looking totally overmatched, well beyond his best days. It became clear that Mosley’s final shining moment against Antonio Margarito in Jan. 2009 was, indeed, a final shining moment — he hadn’t looked very good in his prior fight, and never really looked good again. The Pacquiao bout was a low point, as Mosley couldn’t do anything with Manny’s speed and power, and even lacked the fighting spirit that had been one of his key strengths for years. When Pacquiao dropped him or landed good shots, Mosley kept wanting to tap gloves instead of fight back.

As for Brown, who wasn’t a “boxing guy,” he all but apologized for the awful fight at the end of the show, seeming somewhat embarrassed to have been associated with something that was sold to the public as much more than it had any actual hope of being. HBO and Arum got back on the same page after this, and Manny was back “home” from there.

14) Floyd Mayweather vs Robert Guerrero, 2013

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After a two-month jail stint in 2012 for domestic abuse, Floyd Mayweather returned to the ring after a year off for a fight nobody was much asking to see, but one that came about because Guerrero forced matters, and because Showtime, Mayweather’s new TV partner, needed an opponent.

Showtime people and others basically denied that Guerrero would be Mayweather’s May opponent until it was then gleefully announced. The southpaw from Gilroy, Calif., had beaten Andre Berto to retain the interim WBC welterweight title in Nov. 2012 in a rough, hard-hitting fight, but on paper nobody thought he had much of a shot with Mayweather; styles make fights, and Guerrero’s style didn’t figure to be much trouble for Floyd.

The only way anyone thought he might be able to do some work with Floyd was for him to rough it up, as he’d started doing pretty effectively as a welterweight, having come up from featherweight early in his career. But once Mayweather shook the bit of rust, he took Guerrero’s aggression away quite easily, tearing him up with right hands en route to a wide 12-round decision win.

13) Gennadiy Golovkin vs Vanes Martirosyan, 2018

This was supposed to be a rematch between Golovkin and Canelo Alvarez, following their controversial Sept. 2017 bout, which went to a draw. There was huge hype for Canelo-GGG 2, everyone was stoked on it, it was gonna be a big fight, and it was going to be a good fight.

But then Canelo had some issues failing drug tests, saying it was for “tainted meat,” and while those in power seemed perfectly willing to clear him on that excuse, Alvarez “nobly” stepped aside amidst the brouhaha, leaving Golovkin with no opponent.

Jaime Munguia, a Mexican prospect, was considered, but Nevada wouldn’t sanction it. Golovkin eventually wound up going to California to face Vanes Martirosyan, who was willing to step in and save the date. The fight also moved from HBO PPV to HBO, and wound up a two-round wipeout. I could rank this lower, but for me, this has the advantage of not being a long, drawn-out nothing of a fight. At least it was short and violent. What’s better to you, a two-and-a-half hour movie with nothing special but some artistry in its mediocrity, or whatever direct-to-video mess Nic Cage and the boys can pump out over a tight 81 minutes? Give me the latter.

12) Oscar De La Hoya vs Yori Boy Campas, 2003

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The fight that ultimately started the tradition was a pretty routine title defense at 154 pounds by Oscar De La Hoya, as he faced another tough Mexican veteran in Yori Boy Campas.

Campas was a good fighter, like many, and just not capable of competing on the De La Hoya level. Oscar was in good form here; he was coming off an emotional win in Sept. 2002 over rival Fernando Vargas in a terrific fight, and while Campas gave a legitimate effort, he just had no answers for De La Hoya’s speed and combination punching. The veteran of 85 fights took punishment until his corner threw in the towel just before the end of the seventh round, having seen enough.

11) Canelo Alvarez vs Amir Khan, 2016

Somewhat in the vein of the DTV Nic Cage idea, but also, this really wasn’t a bad fight. Canelo vs Khan came out of left field for everyone. Usually when a fight gets announced, word about it has leaked weeks or months prior, and the actual announcement doesn’t surprise anybody.

But there was no word of Canelo-Khan being negotiated, and then one day, Golden Boy just dropped the graphic on us and the fight was official. Khan was written off by many for the usual reasons — coming up to Caneloweight (155), Amir was going to be small and slight, and he’d had notable chin issues and defensive lapses dating back years. Against a naturally bigger, stronger man, Amir seemed doomed.

And he was doomed, but the five-plus rounds we got weren’t boring. Khan boxed well, used his speed, and led on pretty much every scorecard except for those of judges Glenn Feldman and Glenn Trowbridge; no word on what other Glenns around the world may have thought, to be fair. May have just been a Glenn thing. But then Canelo found him and brutally knocked him out. It was a true highlight reel KO, which is another point in its favor. Not a great fight or one for the Hall of Fame display, but there are bigger problems in boxing than a reasonably entertaining fight that ends in predictable but still incredible devastation.

10) Floyd Mayweather vs Manny Pacquiao, 2015

JOHN GURZINSKI/AFP via Getty Images

THE BIGGEST MONEY FIGHT OF ALL TIME. FIVE YEARS OVERDUE. MAYWEATHER. PACQUIAO.

Back in the earlier days of this here web site, which started in 2006, a lot of the Big Fights I covered would be covered from living room parties or get-togethers. For a while, I even had managed to convince a couple of my friends that boxing wasn’t all bad, and could sometimes even be good. They were there for the Mayweather-Pacquiao Cold War Era, as it were, when everyone knew they should fight each other, but they didn’t.

May 2, 2015 is the last time I had one of those get-togethers. After all those years, everyone got Mayweather-Pacquiao finally. They saw it, they were not impressed, and I don’t know that any of them have watched boxing since.

But this is the definition of “one man’s trash is another man’s treasure,” and another chance to make a movie taste comparison. Some would argue that this was the equivalent of a prestige film, with the great talents on display, but no big fireworks or explosions or whatever. Go look at the critics/audience splits on the Rotten Tomatoes pages for, say, Uncut Gems or Ad Astra from last year. Me? I loved those movies, and generally speaking when a movie like that has that sort of critics loved it/audiences didn’t split, I like the movie.

That said, I thought this fight was, indeed, pretty lackluster. I don’t watch boxing for the same reasons I watch movies. I did not think it was the WORST FIGHT EVER!!!!, but it wasn’t particularly engaging, and Pacquiao’s post-fight complaints about coming in with a shoulder injury didn’t help my view, either.

9) Oscar De La Hoya vs Ricardo Mayorga, 2006

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In Sept. 2004, Oscar De La Hoya fought Bernard Hopkins at a catchweight to fully unify the middleweight division, having robbed defeated Felix Sturm to win the WBO middleweight title in June. De La Hoya had shown against Sturm that he was no middleweight, and in case there was any doubt remaining, Hopkins cemented the fact by knocking Oscar out with a ninth round body shot.

De La Hoya didn’t fight at all in 2005, but came back in May 2006 for a carefully-chosen comeback bout back at 154 against Mayorga, the trash-talking Nicaraguan brawler and former welterweight titlist.

It was a wonderfully constructed return angle — De La Hoya, even past his best, should have been way too good for Mayorga, whose moment in the sun after wins against Vernon Forrest in 2003 had sort of come and gone.

But Mayorga was also entertaining, controversial, and would sell the hell out of the fight by personally insulting and attacking Oscar at any given moment in the lead-up. He did that, and Oscar got to put on his Angry Face and vow comeuppance. It all worked quite well. Oscar and Mayorga sold the comeback, and then De La Hoya beat the piss out of Mayorga before stopping him in the sixth round. It was an entertaining mismatch with an enjoyable bit of salesmanship. Also, I love Mayorga. I just do.

8) Canelo Alvarez vs Daniel Jacobs, 2019

Last year’s Cinco De Mayo weekend fight was the first of the DAZN era, with Canelo having moved there after HBO left the fight game. This was another fight where the opponent we got was denied until it was clear there were no other options, like Mayweather-Guerrero. Oscar De La Hoya repeatedly stated clearly that Daniel Jacobs would not be Canelo’s May opponent. But then he was, because he was basically the only good option they’d agree to face.

Having to go heavy covering this fight last year made me sick to death of this fight by the time it was over, and its tactical nature didn’t exactly thrill me. But with a year of remove from the moment, it wasn’t a bad fight; it wasn’t great, either, but it wasn’t bad. Canelo won a competitive bout against an opponent who is very good, very talented, but just doesn’t seem to have that final gear you need to be truly great.

Also, if it’s not clear by now, this weekend is not exactly heavy on actually great fights. So this ranks where it does. Speaking of which...

7) Floyd Mayweather vs Shane Mosley, 2010

Photo by Jed Jacobsohn/Getty Images

(You can watch the full fight here, and it’s a legal upload, but embeds are blocked on this video for some reason.)

Mayweather-Mosley was another fight that many felt was years overdue. Mayweather had been accused of avoiding Sugar Shane for a long time, but the fight was finally made in 2009, right after Mosley — whose career seemed to be winding down — stunned pretty much everybody by not just beating Antonio Margarito, but absolutely demolishing the Mexican welterweight titleholder in January.

Mosley’s win over Margarito came with the big question mark of Margarito and his trainer having been caught with tainted hand wraps before the fight, which sent Margarito out certainly not in his normal frame of mind, at the very least, and maybe without his normal weaponry. Mosley kicked his ass all over the ring, and made himself a hot property.

Mayweather and team knew, of course, that Mosley was still getting a little old and probably wasn’t as dangerous as he once was. And basically, that wound up being true.

Still, this fight had its one great moment. In the second round, Mosley drilled Mayweather with a clean right hand, shaking Floyd up, a real rarity. A second right hand came in shortly after, buckling Floyd’s knees and dipping him nearly all the way to the canvas.

But Mayweather proved capable of handling the heat, covering up, defending, and not letting the emotion get the better of him. He was largely able to fend Mosley off by tying him up. And once the round ended, Mayweather recovered in the corner and took over the fight, winning handily the rest of the way. You could see Shane Mosley lose himself the rest of the fight; in the corner between rounds, his eyes went vacant. He had no answers, and he knew it.

Round two was really Shane Mosley’s last stand. But it really was an electric couple of minutes, where Floyd Mayweather actually looked genuinely vulnerable. That made this one a fairly memorable fight for me, even though on the whole it was a totally one-sided contest.

6) Manny Pacquiao vs Ricky Hatton, 2009

The atmosphere for this fight was incredible, the anticipation was great. Ricky Hatton was popular and lovable and brought his brigade of Brits back to Vegas for another big fight. He’d also never lost at 140 pounds, where he was an effective mauler with a lot of energy and a good body attack.

It may seem silly now, but as we mentioned the other day, Pacquiao north of 130 was still a question mark in 2008-09. He proved, of course, that he could definitely handle fighting at a high level at 135, 140, and 147, though he only had one fight each at 135 and 140. He’d thrashed David Diaz at 135 in 2008 before the welterweight bout with De La Hoya, and then dropped down to 140 to face LINEAL!!! champion Hatton.

The fight was expected to produce fireworks, and it did. It’s just that all the fireworks were from Pacquiao. Hatton couldn’t do anything about Pacquiao’s blinding speed, odd angles of attack, and stinging power. And we wound up getting one of the great one-punch knockouts ever out of it.

5) Floyd Mayweather vs Miguel Cotto, 2012

Floyd Mayweather’s final bout before his jail stint saw him coming in with, obviously, quite a lot on his mind, and facing a guy in Miguel Cotto who was no patsy. Cotto was one of the best fighters of his generation, and though he’d lost to Antonio Margarito (with an asterisk) and Manny Pacquiao at 147, Mayweather’s style was nothing like Margarito’s or Pacquiao’s.

Floyd was a strong favorite, of course, and should have been. And he did get the win once again, but Cotto was competitive in the fight, even with wide scores for Mayweather being perfectly reasonable. Floyd was just that bit better than Cotto most of the evening, but it was the rare Mayweather fight that most agreed was pretty entertaining, because Cotto made Floyd earn every round. He didn’t go away and he didn’t stop trying.

Mayweather beat Cotto, but he didn’t take Cotto’s spirit the way he had so many others, and that was important in the fight being fun to watch.

4) Floyd Mayweather vs Marcos Maidana I, 2014

Marcos Maidana was another sort of surprise opponent for Floyd in 2014, and boy did Maidana make the most of the opportunity.

Maidana, a sort of crude Argentine slugger/brawler, had lost fights in the past, but you knew what you were getting out of him. And his stock skyrocketed when he humbled Adrien Broner badly at the end of 2013, landing him the fight with Mayweather in May.

Maidana proved a lot more capable of testing Mayweather than much of anyone expected. The rugged, fearless underdog roughed Floyd up to the point of frustration, and what most figured would be a mismatch or even a wipeout turned out to be a gritty, dramatic battle where Mayweather had to dig deeper than he had in some time. All those attempts that quality boxers made to box with him over the years hadn’t worked, and Maidana was no technician, anyway. He aggressively came at Mayweather, wasn’t afraid to get dirty with Floyd (who was good at dirtying up a fight in his own right), and it turned out to be compelling enough that a rematch later in the year was welcome.

3) Oscar De La Hoya vs Floyd Mayweather, 2007

De La Hoya-Mayweather wasn’t the most thrilling fight, but when people talk of high-quality chess match type bouts, or defend, say, Mayweather-Pacquiao with that sort of praise, this is a fight I think of that actually works for me in that way.

De La Hoya brought Mayweather up to 154 pounds, where Floyd could fight but never really belonged. (Floyd went 4-0 fighting north of 147 in his career, beating Oscar, Cotto, Canelo, and Conor McGregor.)

The size advantage for De La Hoya helped him, and he jabbed and boxed very effectively in the first half of the bout. There have been debates about what happened in the second half. Did Oscar abandon the jab, and if so, why? To me it seems insane to “abandon” something that had been working so well, and while I’m no massive De La Hoya fan, I don’t think he was a dumb fighter.

Mayweather took the jab out of the equation. Mayweather adjusted, and De La Hoya wasn’t able to do so on the other side. In the end, Floyd won a split decision, though one without any huge amount of controversy. It was a good fight and, at the time, was the biggest PPV bout of all-time. The build-up with HBO’s first “24/7” series also established the potential for the newly-christened “Money” Mayweather to become a genuine boxing and mainstream sports superstar; the win solidified his rise to a level he knew he could reach, but others had doubted in the past.

This was also the fight that really set the true tradition of this being a marquee Saturday night. Not every matchup has lived up to this level, of course, but this one is really where it all got going in the sense of what the weekend has become for boxing.

2) Manny Pacquiao vs Juan Manuel Marquez I, 2004

The first of four legendary fights between these two. Most multi-fight rivalries have at least one “dull” fight, one that wasn’t so great. Ali-Frazier 2, Gatti-Ward 2, Morales-Barrera 2 were good fights, but didn’t meet the standards of the others in those trilogies for excitement, for instance. Pacquiao-Marquez never had a bum fight. Each one was excellent, and it all started here.

At the time, with Erik Morales and Marco Antonio Barrera the big names in/around this weight class, Juan Manuel Marquez was kind of the “other” Mexican. He was clearly a hell of a fighter, enough that most wanted nothing to do with him. He wasn’t exactly exciting, but he was really, really good, and his lack of star power made him an extra big risk.

But Pacquiao fought him, and the rest, as they say, is history, as the best rivalry of its time started right here. Marquez went down three times in the first round, and frankly, referee Joe Cortez would’ve been forgiven for stopping the fight, and maybe we just never think of this one again.

But Cortez saw that Marquez was still OK to continue, and the fight went on. And on. And Marquez started finding answers for Pacquiao. And Marquez started outboxing Pacquiao, while also proving plenty capable — and willing — to go into the firefights with the Filipino.

The end result was a split draw, with one judge seeing it 115-110 for Manny, another 115-110 for Marquez, and the third coming back even at 113-113. It was a hugely controversial fight, but more in the way that everyone wanted to see it again. We’d have to wait four years for the rematch, but that one was great, too, and the third and fourth fights were also terrific. (If there IS a “dull” fight of the series, I guess it’d be the third one, but I thought that was a great fight.)

1) Diego Corrales vs Jose Luis Castillo I, 2005

I don’t need to say much about this fight. We’ve talked about it many times over the years. Everyone has. It’s largely regarded as the best fight of the 2000s, the best fight of this century so far, and for some, simply the best fight of all-time. Real, actual boxing doesn’t get much more cinematic than Corrales-Castillo, and it takes the top spot on the list for me, without question, and considering how much I love Pacquiao-Marquez I, I mean that as the highest praise.