Top 40 Chicago Sports Moments

CHICAGO’S GOT GAME: Spanning more than 100 years, the city’s 40 most memorable sports moments mix thrilling victories with agonizing defeats

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Top Chicago sports moments

To celebrate our magazine’s 40th anniversary this December, we name the 40 best records, restaurants, movies, and more

10. Panic Button
September 22, 1959
After the White Sox beat the Cleveland Indians to clinch the 1959 American League pennant, Chicago’s fire commissioner, Robert J. Quinn, set off the city’s air raid sirens. Hysterical non-Sox fans took to the streets, convinced that World War III was about to begin.


9. Twilight Zone
September 28, 1938
With night closing in on Wrigley Field, the umpires were ready to call the Cubs’ game against the first-place Pittsburgh Pirates because of darkness, ending it in a tie. But with two outs in the bottom of the ninth, Cubs catcher Gabby Hartnett swung and connected on an 0–2 pitch, belting a game-winning homer into the left-center-field gloom. A mob of delirious players and fans circled the bases with Hartnett, whose “homer in the gloamin’” put the Cubs in first place to stay—and remains the most dramatic hit in Cubs history.


8. Storybook Beginning
June 12, 1991
The best era in Chicago sports began when the Bulls won their first championship, beating the Los Angeles Lakers 108–101 in Game 5 of the 1991 NBA finals. Five more championships would follow. For Michael Jordan, it was an emphatic rebuke to critics who had sniped that he was too selfish, too much of a showboat, to win it all. In the visitors’ locker room after the game, with his father at his side, Jordan broke down as he clutched the championship trophy, his tears an outpouring of joy, relief, and vindication. For a great retrospective on Game 5, watch the video below:


7. Buzzer Beater
March 23, 1963
At Freedom Hall in Louisville, Kentucky, Loyola’s Vic Rouse tipped in an errant Les Hunter jumper with one second left in overtime to give the Ramblers a 60–58 victory—and an NCAA basketball title—over the two-time defending champion Cincinnati Bearcats. For footage from the Loyola game, watch the video below:


6. Overtime Marathon
April 10, 1934
The Blackhawks and Detroit Red Wings were locked in an epic stalemate to claim the 1934 Stanley Cup, playing three periods and two overtimes without scoring a goal. Then the Blackhawks’ Harold “Mush” March shot from 20 feet out and scored. Immediately, the 140-pound March (a “shrimp of a hockey player,” according to one newspaper account) patted Detroit goalie Wilfrid Cude on the back in sympathy and dove into the net, grabbing the puck for a souvenir. More important, the Blackhawks had won their first Stanley Cup.


5. Down to a T
December 8, 1940
In the NFL championship game of 1940, the Bears were itching for revenge against the trash-talking Washington Redskins, whose owner had called the Bears “crybabies” after his team had beaten them a few weeks earlier. On the second play from scrimmage, using the T formation they had perfected that season, the Bears scored on a 68-yard run by Bill Osmanski—a taste of the carnage to come. By the time it was over, the Bears had their revenge, 73–0, the most lopsided trouncing in NFL history. After this game, most pro teams rushed to adopt the potent T formation, and the modern era of football was born.


4. Solo Series Shot
October 23, 2005
With Game 2 of the White Sox–Astros World Series tied 6–6 in the bottom of the ninth, Sox outfielder Scott Podsednik, who had not hit a home run during the regular season, launched a Brad Lidge fastball into the right-field stands. The Sox were on their way to a sweep—and the city’s first baseball championship since 1917.


3. The Shot
May 7, 1989
Heading into the first round of the 1989 playoffs, the Cleveland Cavaliers were considered one of the best teams in the NBA, and the Bulls a good team with a great player. But everything changed in the deciding Game 5. With three seconds to go and the Bulls down by one, Michael Jordan nailed a double-pump 15-footer over Craig Ehlo. Jordan’s celebration was almost as good as the shot: leaping, punching the air with his fist, and yelling, “Go home!” to Cleveland’s fans. The Bulls failed to reach the NBA finals that year—losing to the thuggish Detroit Pistons in the conference finals—but “the shot” announced that their time was coming. Watch Michael’s game-winner—and his reaction—in the video below:


2. The Long Count
September 22, 1927
In the seventh round of the most ballyhooed fight of the Jazz Age, 105,000 spectators at Soldier Field watched Jack Dempsey stagger Gene Tunney with a thunderous left hook, then drop him to the canvas with a flurry of blows. But Dempsey failed to retreat to the farthest neutral corner, as the rules required, and the referee delayed the start of his count. That bought Tunney crucial extra time to recover, and he went on to win what came to be known as the “battle of the long count”—one of the most controversial bouts in boxing history.


1. The Finale
June 14, 1998
In a career packed with big shots in gut-check moments, Michael Jordan conjured up a grand finale. His last shot as a Bull was a game-winning 17-foot jumper, after which he held his follow-through for an extra beat, his arm extended like an exclamation point. The shot defeated the Utah Jazz, gave Chicago its sixth NBA title and second three-peat, and proved Jordan could do just about anything—even arrange the perfect goodbye. Watch video of his final shot below:

Photo gallery



4 years ago
Posted by IshyMoose

Where is Disco Demolition and that Monday Night game against the Cardinals from a few years ago?

4 years ago
Posted by lost in windy

maybe I missed it. Where was the 85 Bears Super Bowl win?

4 years ago
Posted by john3222


4 years ago
Posted by LWK

This is some kind of a joke, right? Who are these people that put this asinine list together? There is nothing about this that can be taken seriously by anyone who knows anything about Chicago sports.

4 years ago
Posted by Kurt5

Are you joking? The White Sox won the World Series in 2005, yet you don't list any of the "moments" from that season. Also, you should have one of the times during the 1985 Bears season when William "Refrigerator" Perry steamrolled over defenders for a touchdown. Notwithstanding their success this year, the Blackhawks have been the least popular professional sports team in Chicago for decades, yet you mentioned numerous Blackhawks moments on this list.

4 years ago
Posted by Bugsie

Nick, JY and I cut New Trier in 62 or 63 to visit Wrigley. Mets 19, Cubs 3 which prompted a NY paper to proclaim: Mets score 19; but did they win?

4 years ago
Posted by doctorknow

If Northwestern's Wildcats are a Chicago team (even though they are in Evanston) maybe northwest Indiana should be included in the geographic metro definition. In that case, you should have included 'the shot' when Bryce Drew led Valpo to its first NCAA Tournament victory, defeating 4th seeded Ole Miss in the first round. That unbelievable moment was telecast all over the world.

4 years ago
Posted by soxfanno1

As much as I love reading the Cubs misfortunes, I would like to hear more good moments in Chicago sports history. Why is there no list of Buehrle's no-no in 2007? I realize that his perfect was reported, but it focussed more on Dewayne Wise than Buehrle. Is it just that there aren't 40 "good" moments in Chicago sports, because I can think of 11 different games from October 2005 alone!

4 years ago
Posted by magoos0728

Dear Editor of Chicago Magazine,
While I was excited to see that you included an article that reviews the greatest sports moments in our cities history, I was horrified after reading this piece. Noah Isackson, Geoff Johnson, and Shane Tritsch should all be fired immediately. If this is their definition of investigative journalism, I would review what they have written in the past. It was simply awful. I won't get in to specifics, I'll just say that this article sucked.

Yet another reason I do not read your magazine.

4 years ago
Posted by brukschmd

So many omissions, I have to agree with some of the comments above. 1) Gale Sayers' 6 touchdowns against the Niners. Like Koufax in baseball, Sayers has a place in the HoF despite a short career because of his brilliance. No one did it better. After scoring 5 on a rainy Sunday at Wrigley, Halas sat Gale but put him in for a 4th quarter punt return in response to the fans' plea. Sayers zigged and zagged the length of the field as Niners defenders slid futilely past him with each cut. 2) Ernie Banks' 500th homerun against Pat Jarvis, a line shot barely over the wall with Brickhouse'"Hey Hey" and 500 flashing on the WGN screen. 3) There was no baseball player in the 50's more revered than Stan Musial. The Man's 3000th hit in 1958 was a double at Wrigley. At the time Musial was the first to attain 3000 since 1942 and the eighth in baseball history.... I have other personal memories--Don Cardwell throwing a no-hitter in his first game after being traded to the Cubs, Ditka clotheslining a fan streaking across "his workplace", Bobby Hull knocking Gump Worsley cold with a slapshot to his forehead--down like he was shot by a sniper-- but surely the 3 have to be included in big sports moments in Chitown.

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