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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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Michael Jordan and Scottie Pippen
#14—WOUNDED WARRIOR: An ailing Michael Jordan stumbles into the arms of teammate Scottie Pippen after the Bulls’ Game 5 of the NBA finals against the Utah Jazz. For more photos of great Chicago sports moments, check out the photo gallery »



Top Chicago sports moments

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

Chicago is a Bears town. It’s also a Sox, Cubs, Hawks, and Bulls town. (We also like a good horserace, a fierce prizefight, and the occasional Olympic moment.) In good and (more often) bad times, we remain rabid about our sports teams: second-guessing our coaches, criticizing our players, and all too rarely reveling in a championship season.

So now that we have assembled our roster of the 40 most memorable and significant Chicago sports moments, is there any reason to expect it will be greeted with equanimity? Hell, no! Let the disputes begin—preferably over a cold beer at a local tavern. Once you’ve figured out where we went terribly wrong, let us know in the comments section below.

PLUS: Check out some great Chicago sports moments in our photo gallery »


40. Plaintive Plea
September 28, 1920
One of Chicago’s most memorable sports moments might be apocryphal: After White Sox left fielder “Shoeless” Joe Jackson concluded his testimony before a grand jury about throwing the World Series, a young boy confronted him and pleaded, “Say it ain’t so, Joe”—a remark that would come to symbolize the ugly Black Sox scandal of 1919.


39. Flivver Follies
November 28, 1895
Beginning at about 9 a.m. on Thanksgiving Day, with six inches of snow on the rutted streets, six cars took off from Chicago’s Jackson Park in the country’s first organized automobile race. Ten hours and 17 minutes later, after completing the 55-mile roundtrip to Evanston, the car built and driven by Frank Duryea was pushed across the finish line to take the $2,000 first prize.


38. Municipal Pastime
November 30, 1887
When football fans inside the gym at Chicago’s Farragut Boat Club learned that Yale’s Bulldogs had defeated the Harvard Crimson, an exultant Yale man tossed a boxing glove at a Harvard alum, who swung at it with a broomstick. With the glove bound up like a ball, a full-fledged game ensued—final score: 43–42, though nobody remembers who won—and softball was born.


37. NIT Picker
March 26, 1945
When the National Invitational Tournament still decided college basketball’s champion, DePaul University’s George Mikan, the team’s six-foot-ten center, set several scoring records— including 53 points in a semifinal victory over Rhode Island State—en route to DePaul’s stomping Bowling Green of Ohio 71–54 in the final at Madison Square Garden. For more on Mikan, watch the video below:


36. Crash of ’29
October 12, 1929
A few weeks before the stock market crash ushered in the Great Depression, the Cubs suffered “the greatest debacle, the most terrific flop” in World Series history, according to a Tribune account. Leading the Philadelphia A’s 8–0 in Game 4 of the series, the Cubs surrendered ten runs in a nightmare seventh inning and lost the game. Fueling the meltdown was center fielder Hack Wilson, who lost two routine fly balls in the sun in the inning—the second rolling to the wall for a three-run homer—putting him “at the head of the list of world series goats,” the Trib said. He would not be the last goat to spoil a Cubs postseason. For footage of the series, watch the video below:


35. Purple Power
September 2, 1995
On fourth and two at the Notre Dame 44, Fighting Irish running back Robert Farmer plowed into a purple wall of Northwestern defenders for a gain of only one yard. A capacity crowd at Notre Dame Stadium then watched in shock as Northwestern ran out the clock for a 17–15 victory. The perennial patsies of college football (23 straight losing seasons), the Wildcats had just pulled off “The Upset of the Century,” as the Sun-Times proclaimed, against the ninth-ranked, 27-point favorite, football powerhouse Notre Dame. But in the weeks ahead, Northwestern proved this was no fluke, going undefeated in the Big Ten and earning the school’s first Rose Bowl berth (a tense 41–32 loss to USC) since 1949. Watch NU’s victory unfold in the video below:


34. Tarzan in Paris
July 20, 1924
The 20-year-old star of the Illinois Athletic Club, Johnny Weissmuller had been shattering swimming records—including those held by Hawaii’s Duke Kahanamoku—since he began competing in 1921. For the first of his three gold medals at the summer Olympics in Paris in 1924, the future movie Tarzan set a new Olympic record in the 100-meter freestyle with a time of 59 seconds. His teammate Kahanamoku trailed him by more than two seconds to take the silver.


33. Ice Breaker
March 12, 1966
When the Blackhawks met the New York Rangers at the Chicago Stadium, only three NHL players had ever scored 50 goals in a season: Rocket Richard, Boom Boom Geoffrion, and the Hawks’ Bobby Hull. For years that 50-goal plateau had seemed insurmountable—yet five and a half minutes into the third period, the Golden Jet, poised at center ice, sent a slap shot past Ranger goalie Cesare Maniago, giving Hull his magical 51st goal (he’d end up with 54 for the season). The Hawks went on to win 4–2, but only after a long delay to clear the ice of all the debris tossed by ecstatic hometown fans. Watch Hull’s goal below:


32. Cat o’ ’69 Tales
September 9, 1969
The comfortable lead that the first-place Cubs had enjoyed throughout the summer of 1969 was almost gone when they played the surging Mets in a crucial late-season game in New York. In the first inning, a black cat darted past Ron Santo, the Cubs’ on-deck hitter, and through the Cubs’ dugout. The Cubs lost the game, fell out of first place the next day, and collapsed down the stretch. The ill fortune portended by the cat was “just stupid superstition, right?” asked the Tribune. Right.


31. Cardinal Virtue
December 28, 1947
Two weeks after defeating the Bears for the NFL’s western division championship, the Cardinals—Chicago’s other football team—faced the Philadelphia Eagles at frigid Comiskey Park for the title. After three exciting TD runs by the team’s “Dream Backfield”—including a 75-yard punt return by the future Hall of Famer Charley Trippi—the Cards clinched what would be a 28–21 victory with a 70-yard run up the middle by Elmer Angsman—giving him an average of 15.9 yards per carry, still a single-game playoff record. For more on Trippi, watch the video below:


Photograph: Chicago Tribune photo by Nuccio Di Nuzzo

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