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The Worst Chicago Sports Losses of All Time

The Black Sox Scandal, the Sneaker Game, the Coin Toss, and more.

Photo: Jonathan Daniel/Getty

Five seconds left in the NFC Wild Card game. The Bears are on the Eagles’ 26-yard line, trailing 16 to 15. Cody Parkey runs on to attempt a game-winning field goal, gets iced, and tries again.

The snap. The kick. The ball is up. It grazes the fingers of defensive tackle Trayvon Hester. Then it bounces off the left upright, then the crossbar, and flops onto the field, as mascot Staley Da Bear falls over on his side, as though he’s been shot.

Thus ends the season of the most exciting Bears team since 1985. It was a tough beat, but Chicago sports teams have experienced tougher: defeats that haven’t just ruined seasons, but damaged franchises for years to come. Let’s recall some of the worst.

The Black Sox Scandal:

This year marks the hundredth anniversary of baseball’s most infamous World Series, when eight members of the Chicago White Sox, including would-have-been Hall of Famer Shoeless Joe Jackson, were banned from baseball after allegedly conspiring with gamblers to throw the Series to the Reds.

This was probably the worst beat Chicago has ever experienced, because it was both self-inflicted and damaged the team for decades.

In the early 20th Century, the White Sox were among baseball’s elite, appearing in three of the first 16 World Series. But after losing most of their best players, the team descended into eternal mediocrity. Since the Scandal, they’ve only been back to the Series twice, and are arguably the most anonymous and least distinguished of baseball’s original 16 franchises.

The Scandal also resulted in the appointment of baseball’s first commissioner, Kenesaw Mountain Landis, a Chicago federal judge and staunch racist who kept black players out of the game until his death in 1944.

The Sneaker Game:

It was cold and wet in Manhattan on December 9, 1934, when the undefeated Bears met the New York Giants in the NFL Championship game. Throughout the first half, both teams slipped and slid on the frozen turf, which was too hard for cleats to gain traction. Only the Bears managed a touchdown, on a pass from quarterback Keith Molesworth to fullback Bronko Nagurski. At halftime, they held a 13-3 lead.

Inside the locker room, though, the Giants made an equipment change that turned out to be decisive: they exchanged their cleats for rubber soled basketball shoes. According to the next day’s New York Daily News, “What really won the game was Coach Steve Owen’s order that all hands unlace their leather cleats and don rubber sneakers. This gave the Giants a purchase on the icy field, especially on spinner plays and reverses.”

In the fourth quarter, the sure-footed Giants scored four touchdowns, while the Bears continued skidding around the field.

The Coin Toss:

In 1969, the Bears and the Pittsburgh Steelers both finished 1-13. To determine who got the number one pick in the next year’s draft, representatives of both teams met for a coin toss in a New Orleans hotel room. As NFL Commissioner Pete Rozelle held a 1921 silver dollar, Ed McCaskey, the ne’er-do-well son-in-law of Bears founder George Halas, called “heads.” The coin came down tails.

“McCaskey, you bum, you can’t even win a coin toss!” a Sun-Times sportswriter shouted.

The Bears ended up losing a lot more than a coin toss. They lost the right to pick Louisiana Tech quarterback Terry Bradshaw, who would lead the Steelers to four Super Bowl victories. The Bears still haven’t had a great quarterback since Sid Luckman, who thrilled the nation with his T-formation until his retirement in 1950.

Disco Demolition Night:

By 1979, the backlash against urban dance music was on full blast. That July, the White Sox and WLUP disc jockey Steve Dahl invited fans to attend a doubleheader against the Tigers for 98 cents if they bought a disco album to be blown up on the field between games.

The Sox were struggling through a 73-87 season, and owner Bill Veeck was always willing to use any gimmick to bring in fans. Nearly 50,000 showed up, many wearing WLUP t-shirts. As Dahl destroyed disco, drunken fans stormed the field, causing so much damage to the grass that the White Sox were forced to forfeit the second game.

“It was a vibe unlike any other,” Comiskey Park beer vendor Bob Chicoine recalled in 2017, during a panel discussion at the Elmhurst History Museum. “All these kids, and mind you the drinking age for beer and wine was 19 then … but there was a sense of elation and anticipation. Youthful exuberance. You knew something was going to happen. Mid-game we were pouring as fast as we could, and one guy told me ‘They ain’t gonna play Game 2.’.”

The Bartman Game:

You know the story.

The Cubs took a 3-0 lead in the eighth inning of Game 6 of the 2003 National League Championship Series at Wrigley Field. Fox announcer Thom Brennaman was counting down the outs to the team’s first pennant since 1945. “Five outs away,” he said as the Marlins’ Luis Castillo stepped to the plate.

Castillo hit a foul ball off starter Mark Prior. As the ball spun toward the box seats behind the left field line, clueless fan Steve Bartman reached for it, deflecting its path from the glove of left fielder Moises Alou. An unnerved Prior followed up with a wild pitch. Castillo walked. Juan Pierre, who had reached second base on a double, advanced to third. Both scored. So did six other Marlins, giving the visitors an 8-3 victory.

There was still a Game 7, but everyone knew the Cubs were going to lose it. “I talked to a friend in Las Vegas, and the money is pouring in on the Marlins,” one of my gambling buddies told me the next day. Lose the Cubs did. They would have to wait another 13 years to reach a World Series.

The game, and the freak play that changed its course, has become such a part of Chicago sports lore that Bartman is better remembered than any of the Cubs who were on the field that night. Bartman has never returned to Wrigley Field, and attempts to live an anonymous life in the north suburbs. When the Cubs won a World Series, the team gave him a ring.

Derrick Rose’s knee injuries:

If Derrick Rose had led the Bulls to an NBA championship, he may have been the most beloved player in the team’s history. Michael Jordan, for all his talent, is not a lovable character, and he’s from North Carolina. Rose grew up in Englewood and won a state championship for Simeon Career Academy.

The Bulls took Rose with the first pick of the 2008 NBA draft. In 2010-11, he led the team to a league-best 62-20 record and became the youngest winner of the Most Valuable Player Award. The next season, again with the league’s best record, the Bulls entered the first round of the playoffs as big favorites against the Philadelphia 76ers. In Game 1, Rose tore the anterior cruciate ligament in his left knee. The Bulls lost the series, four games to two. Rose missed all of the following season, and most of the season after that, with a tear to the meniscus in his right knee.

Ever since, the player who once looked like the future of Chicago basketball has been a journeyman. Since leaving the Bulls after the 2015-16 season, Rose has played for the Knicks, the Cavaliers, and now the Timberwolves, where he is reunited with old coach Tom Thibodeau, and is averaging 18.9 point a game, the highest total since before his first injury. Rose is only 30, so maybe he can once again become an all star.

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