Sweet Home Chicago: The Ten Biggest Boxing Matches in Windy City History

Chicago is not a city that fails to embrace professional sports. So where has boxing gone in the Windy City? (Photo by Jonathan Daniel/Getty Images)

James Foley returns to Bad Left Hook this morning with a simple and valid question: What happened to boxing in the city of Chicago?

As a frustrated boxing fan in Chicago, I often wonder why my humble city no longer plays host to any big prize-fights. This isn't a recent development; it's been decades since the city was any kind of a player. One look at Chicago's unique ethnic blend, top-three in the country in African-American, Mexican, and Puerto-Rican populations, seems to indicate serious potential to once again become a major market in the sport. It would help if there were a local product to rally around. If not, I'm cool adopting Sergio Martinez. Decent Argentine population here as well.

One of my other stock arguments is ‘the city has one of the richest, most storied traditions in boxing' and a little research makes that undeniable. It may have been fifty years since the last entry, but Chicago was home to some of the biggest, bloodiest, most significant matches in the history of the sport. I would even go so far as to suggest if you made a top ten list for every city in the world, only New York and Las Vegas would slightly edge Chicago in terms of the fights they've produced. Here are ten of the most notable fights that have taken place here.

1. Gene Tunney (64-1-1) UD Jack Dempsey (61-6-9)
September 22, 1927
Soldier Field


Jack Dempsey was the unstoppable force of the heavyweight division from 1919-1923. After a three-year layoff, he took on Gene Tunney in 1926 and was easily out-boxed by the faster, technically superior challenger. They met again, almost a year to the date, and the first six rounds unfolded much like the original. Tunney circled the plodding Dempsey, not as quick as he once was but still just as crude, picking him apart with combinations from the outside. Every step forward from Dempsey was met with two steps sideways from the nimble Tunney. He had gone sixteen rounds with the Manassa Mauler and not once was he remotely threatened by Dempsey's fearsome power.

In the seventh, lightning struck for Dempsey. He caught Tunney with a big right and followed up with a barrage of unanswered shots, featuring a wicked left hook that snapped Tunney's jaw as he crumpled to the canvas. Shockingly, Tunney appeared just fine as he wisely sat on one knee and took as much time as he could to recover. The problem was Dempsey hadn't gone to a neutral corner right away and a few seconds elapsed as referee Dave Barry ordered him to do so. Thus the ten-count began four or five seconds late, and when Tunney arose at "nine", he had actually been down fourteen seconds. Tunney scurried away for the final minute of the round and went back to his methodical ring ballet to cruise to another unanimous decision win. Dempsey would never fight again and "the long count" still ranks as one of the greatest boxing controversies of all time.

2. Sugar Ray Robinson (121-1-2) TKO13 Jake LaMotta (78-15-3)
February 14, 1951
Chicago Stadium


Sugar Ray Robinson first met Jake LaMotta in 1942 and out-boxed him to a unanimous decision win. In 1943, LaMotta handed Robinson (then 40-0) his first loss. Over the next eight years, Robinson compiled a modest record of 80-0-2, including three wins, a couple very close ones that could have gone either way, over LaMotta. It wasn't until their sixth contest, at Chicago Stadium, that Sugar Ray truly got revenge on his one-time conqueror. More than five years had elapsed since their previous meeting, a split decision win for Robinson in 1945. LaMotta went on to become the middleweight champion in 1949 after beating the stuffing out of an injury-riddled Marcel Cerdan. Robinson was the welterweight champ, moving up in weight to challenge LaMotta for his title.

While LaMotta had previously used his size and awkwardness to rough up Sugar Ray, this time Robinson was fully bulked up to a middleweight, stronger and savvier than he had been before. Robinson fought fire with fire. The power, precision and speed were too much for LaMotta to handle. But the "Raging Bull" never stopped coming. LaMotta had a brick wall for a jaw. He had never been legitimately stopped. In the thirteenth round, Robinson unloaded on him, battering the maniacal LaMotta all over the ring. Jake remained on his feet. Mercifully, after what seemed like an eternity of a beating, the referee stopped the fight, and bear in mind, in those days, fights were rarely stopped unless at least one participant was no longer conscious. At that point, LaMotta may or may not have uttered the immortal line from the film Raging Bull: "You never got me down, Ray." The fight is fondly remembered as the "St. Valentine's Day Massacre". What a chin.

3. Sonny Liston (34-1) KO1 Floyd Patterson (38-3)
September 25, 1962
Comiskey Park


Floyd Patterson, the champion, was a very good boxer-puncher, athletic and quick. Unfortunately, he was woefully small for a heavyweight and wore one of the more fragile chins in division history. The challenger Sonny Liston knocked people out with his jab. This fight had disaster written all over it for Patterson and indeed it played out to the worst of those expectations. Liston patiently stalked until Patterson found himself back to the ropes about halfway into the first round. He caught Patterson flush with a left and the damage was immediately obvious. Patterson writhed as he desperately sought to escape but there was nowhere to go. He got tangled in the ropes and Liston cracked him with a left hook. Floyd went down hard, came to his wits, and perched on a knee, getting in position to beat the count. Yet he never arose. He just sat there marveling at the power that had knocked him senseless and would probably do so again if he made the unwise decision to get up. Liston became the heavyweight champion.

4. Joe Louis (32-1) KO8 Jim Braddock (45-24-4)
June 22, 1937
Comiskey Park


Jim Braddock was an everyman. Joe Louis was a superman. Those match-ups don't usually work out well for the underdogs and this was no exception. Braddock became "the Cinderella Man" when he upset 10-1 favorite Max Baer to win the heavyweight championship in 1935. He backed out a fight with Max Schmelling to take a bigger payday against Louis. He also smartly negotiated a percentage of Louis' future earnings to give Louis the shot at the title. Braddock's own boxing career was just about over. The beginning of the end was the brief glory of knocking down Louis in the first round. Louis got over-aggressive and Braddock caught him with a pinpoint counter to put him down. Louis wasn't hurt. From there, Louis mounted a more efficient attack, and the superior speed, athleticism and power were evident. Braddock took a licking, too much heart for his own good as he stubbornly refused to let his corner end the fight. In the eighth round, a diabolical right-hand bomb from Louis did the job for them.

5. Barney Ross (44-2-2) MD Tony Canzoneri (92-13-8)
June 23, 1933
Chicago Stadium


In the 1930s, the lightweight division was the place to be for good old-fashioned ethnic rivalry bloodbaths. This fight doesn't quite rank with the epic trilogy between Barney Ross, hero of the Jewish immigrants, and Jimmy McLarnin, hero of the Irish, that took place in 1934-1935. But from a historic perspective, it was a significant meeting between two of the best lightweights of all time. Tony Canzoneri, fighting for the Italian contingent, pressed the action in the ten-round championship fight, while the slicker Ross bobbed and feinted and worked his jab to keep distance. One judge scored a draw, while two gave Ross the majority of the rounds. Depending on your country of origin, either Ross gave Tony a boxing lesson or the great Canzoneri was robbed. It was a good fight and a significant chapter in the McLarnin-Ross-Canzoneri triumvirate of terrific lightweight fighters with rabid, blindly ethnically motivated fan-bases.

6. Sugar Ray Robinson (141-6-2) SD Carmen Basilio (52-13-7)
March 25, 1958
Chicago Stadium


Sugar Ray Robinson faced Carmen Basilio at Yankee Stadium in 1957 and lost a grueling war that was named Ring Magazine Fight of the Year. The fight was so good, and Robinson's pride so wounded, the only logical thing to do was run it back. The rematch in Chicago was the 1958 Fight of the year. This time, Robinson eked the controversial split-decision. The image of Basilio, left eye swollen completely shut, unwavering in his attack, is one of boxing's most enduring.

7. Rocky Graziano (46-7-5) TKO6 Tony Zale (63-17-2)
July 16, 1947
Chicago Stadium


Rocky Graziano and Tony Zale took each other to hell and back over the course of their famed trilogy from 1946-1948. The second edition in Chicago, the 1947 Ring Magazine Fight of the Year, was perhaps the bloodiest, most dramatic entry in the series. Graziano rallied from a nasty gash and a knockdown in the third round to come back and brutally stop Zale in the sixth. After the fight, Rocky uttered those famous words that would become the title of the movie based on his life: "Somebody up there likes me". He also commented "that Zale ain't no slob".

8. Ezzard Charles (61-5-1) UD Jersey Joe Walcott (44-14-2)
June 22, 1949
Comiskey Park


The rivalry between Ezzard Charles and Jersey Joe Walcott was not a particularly venomous one. These were hard-working, humble gentlemen who favored sportsmanship over gamesmanship. The four-fight series that began in Chicago would produce many classic moments. Charles put on a show in the second fight, routing Jersey Joe with workmanlike efficiency. Joe came back with a breathtaking knockout to wrest the heavyweight championship from Charles in the third. This first entry was not a particularly great fight, as Charles took a mundane decision. But it set in motion Charles as the man who would go on to challenge and defeat Joe Louis the following year, ending his incredible run as heavyweight champ. And it began one of the best rivalries of the era between two of the best fighters of the era.

9. Rocky Marciano (44-0) KO1 Jersey Joe Walcott (51-18-2)
May 15, 1953
Chicago Stadium


In 1952, the crafty Jersey Joe Walcott had befuddled and perplexed Rocky Marciano for twelve rounds, winning handily on all three scorecards. It was a fifteen round fight. In the thirteenth, Marciano found Walcott on the ropes and hammered him with a crushing right hand that seemed to impound Jersey Joe's face. Joe slumped to the canvas, a horrific scene, often considered the most devastating knockout ever delivered. The rematch in Chicago would offer none of the drama or intrigue of the first bout. Marciano walked right through Walcott and put him away with another right hand just over two minutes into the fight. Walcott remained conscious this time but a lackadaisical effort to beat the count made this one of the most disappointing heavyweight championships ever fought.

10. John L. Sullivan (34-0) PTS Jack Burke (22-2-6)
June 13, 1885
Driving Park Racetrack


This was the first significant prize-fight held in Chicago. John L. Sullivan, the legendary bare-knuckle brawler turned first heavyweight champion, took on gritty middleweight Jack Burke and won on points after five rounds with both men standing. Burke was outweighed by almost seventy pounds and became just the third man to last the distance with Sullivan. Sullivan was reported to have been binge-drinking and feasting into the wee hours every night leading up to the fight. Anyone who's not a fan of John L. Sullivan and his mustache might want to consider following a different sport.

Honorable Mentions

Floyd Patterson (30-1) KO5 Archie Moore (159-21-8)
November 30, 1956
Chicago Stadium

The up-and-coming Patterson knocked out the wily veteran Archie Moore to become the youngest man to win the heavyweight championship.

Willie Joyce (52-9-7) UD Henry Armstrong (144-19-8)
June 2, 1944
Chicago Stadium

In the heyday, Chicago played host to many of the greatest fighters who ever lived, including Henry Armstrong, the three-division champion and one of the all-time pound-for-pounders. Armstrong was edged out by slick Willie Joyce, of nearby Gary, Indiana, in a solid, action-packed fight. Joyce's next fight was a ten-round shutout loss to some guy named Willie Pep at Comiskey Park. He then re-matched Armstrong and lost. How's that for a three fight stretch? Armstrong, Pep, Armstrong. By the way, those fights took place over the course of two months.

Sugar Ray Robinson (140-5-2) KO5 Gene Fullmer (40-4)
May 1, 1957
Chicago Stadium

Reason #249583 why Robinson is the best fighter of all-time: he wasn't a man who let losses go un-avenged. He lost to LaMotta, he beat him five times. He lost to Randy Turpin, he rallied in their second fight to brutally stop him. He lost to Basilio and beat him in a rematch. So when Gene Fullmer mauled and gored his way to a decision over Robinson to seize the middleweight championship in January, 1957, you could bet there was retribution coming. The rematch five months later at Chicago Stadium produced one of the most famous knockouts of all time. In the fifth round, Robinson caught Fullmer square on the chin with one of his signature left hooks. Sugar Ray's speed had gone. His power was strikingly intact. Fullmer would've gotten up but his legs were somewhere in Lake Michigan.

Battling Nelson (30-8-12) NC Daredevil Tildon (0-1)
September 3, 1903
Flynn's Hall

And finally, who can forget this illegal 1903 contest between Danish sensation Battling Nelson and nemesis Daredevil Tildon, whose previous exploits included high-diving into a tank of water on his bicycle. In the brawl at Flynn's Jall (no, not the arcade from Tron), both men were down and bloodied by the end of the first round. In the second, the seasoned Nelson was laying a beating on Tildon until Daredevil's better half shouted for the police. The participants disassembled into the back-room to hide and the fight was officially deemed a no-contest. Suffice it to say, this would be Daredevil's lone foray into the sweet science.

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