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Worst moments in Chicago Bears history

Kevin Kaduk
Flags flew at half-staff outside Solider Field following the death of Walter Payton. (AP)
Flags flew at half-staff outside Solider Field following the death of Walter Payton. (AP)

What are the worst moments for each NFL franchise? Yahoo Sports provides our opinion, which you are free to disagree with (and we’re sure you will).

Bears Best Moments | All 32 Teams Best Moments | All 32 Teams Worst Moments

5. Kelvin Hayden intercepts Rex Grossman in Super Bowl XLI

The ensuing narrative out of the Chicago Bears’ only other trip to the Super Bowl was that they were never in it after frittering away Devin Hester’s opening kickoff return for a touchdown. The truth is they still had a chance to steal a win, as the Bears only trailed the Indianapolis Colts by five points entering the fourth quarter. But while Hester and the defense saved the Bears from Rex Grossman all season long, it couldn’t get the team past the quarterback’s last landmine. Three minutes into the quarter, Grossman served up an interception to Colts defensive back Kelvin Hayden – a Chicago native, no less – who returned it 56 yards to give Indianapolis a 29-17 lead that would prove insurmountable. Instead of watching a fun team get crowned with a Super Bowl title, Bears fans had to watch Peyton Manning lift his first Lombardi Trophy with a Colts team that was far from his best.

4. Walter Payton doesn’t score in Super Bowl XX

If anything tells you about the dominance of the Bears over the Patriots, it’s this: They were so good that Chicago residents are still arguing over who should have scored the touchdowns in the 46-10 route. Though such a thing may seem silly, there’s no arguing Walter Payton should have gotten the call for one of them. The Hall of Fame running back carried the franchise for years and plunging into the end zone would have been the ultimate crowning moment for his career. Instead, Mike Ditka handed the ball off to William “The Refrigerator” Perry for a one-yard plunge, a move that left Payton devastated. In the years following Payton’s death, Ditka would admit that passing up on Payton to score in the Super Bowl was the biggest mistake of his coaching career.

3. Jay Cutler hurt in 2011 NFC championship

Bears fans still aren’t ready to talk about this one. The 2011 NFC championship game against Green Bay was only the second playoff meeting between the two bitter rivals and the winner would give their fans the ultimate bragging rights with a trip to the Super Bowl. The Bears hosted the game as NFC North champions, but their fortunes quickly took a turn in the second quarter when Jay Cutler suffered a knee injury that would later be revealed as a torn MCL. The Bears offense was immediately handcuffed with backups Todd Collins and Caleb Hanie, and the Packers, who were only in the playoffs because they beat the Bears in Week 17, walked away with a 21-14 victory (as well as a Super Bowl title two weeks later). Making matters worse, Cutler’s toughness was questioned, as many fans believed he could have re-entered the game. Though those assumptions were unfair, it set the tone for Cutler’s tumultuous tenure in the Windy City. The Bears haven’t been back to the playoffs since.

2. Charles Martin’s cheap shot of Jim McMahon in 1986

For all the boasting Chicago does over the ‘85 Bears, there remains a sense of sadness over the dynasty that never was. Part of that has to do with the NFC being absolutely loaded in the late ‘80s, while another part was self-inflicted. The stardom of the ‘85 team inflated a lot of egos and the departure of Buddy Ryan to the Eagles certainly didn’t help matters. There is one outside influence, however, that irks Chicagoans to this day. On Nov. 23, 1986, Green Bay defensive lineman Charles Martin showed up to Soldier Field carrying a “hit list” of Bears numbers written on a towel. And after Jim McMahon threw an interception, Martin executed one of the worst cheap shots the league has ever seen, body-slamming McMahon to the ground, right on his throwing shoulder. The hit knocked McMahon out for the season, and while the Bears would finish with a 14-2 record, the McMahon-less Bears were upset by the wild card Redskins 27-13 in the playoffs. It was the beginning of the end of the dynasty that never was. Another loss to Washington in the ‘87 playoffs and a blowout loss to the Niners in the ‘88 NFC championship would help start a title-free drought that has now reached 32 years.

1. The death of Walter Payton

Chicago loves its Bears legends, but none more so than Walter Payton, who was exalted for both his talent and toughness. After retiring as the NFL’s all-time leading rusher in 1987, Bears fans looked forward to decades of the kind and charitable “Sweetness” serving as the franchise’s elder statesman. Life had different plans. Payton was afflicted with a rare liver disease that claimed his life on Nov. 1, 1999. His death was mourned across the city and his memorial service was held at Soldier Field. He was 45 years old. While the Soldier Field stands are still packed with hundreds of fans wearing No. 34 jerseys each game day, Payton’s absence leaves a big void both for the club and the NFL. The league’s Man of the Year award now bears his name.