Chicago Bears: The 5 Worst Moments of the Past Decade

CHICAGO, IL - NOVEMBER 20: Jay Cutler #6 of the Chicago Bears runs for a first down as Quentin Jammer #23 of the San Diego Chargers pursues at Soldier Field on November 20, 2011 in Chicago, Illinois. The Bears defeated the Chargers 31-20. (Photo by Jonathan Daniel/Getty Images)
CHICAGO, IL - NOVEMBER 20: Jay Cutler #6 of the Chicago Bears runs for a first down as Quentin Jammer #23 of the San Diego Chargers pursues at Soldier Field on November 20, 2011 in Chicago, Illinois. The Bears defeated the Chargers 31-20. (Photo by Jonathan Daniel/Getty Images) /
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TAMPA, FL – NOVEMBER 27: Kyle Orton #18 of the Chicago Bears handles the ball against the Tampa Bay Buccaneers during their game on November 27, 2005 at Raymond James Stadium in Tampa, Florida. (Photo by Streeter Lecka/Getty Images)
TAMPA, FL – NOVEMBER 27: Kyle Orton #18 of the Chicago Bears handles the ball against the Tampa Bay Buccaneers during their game on November 27, 2005 at Raymond James Stadium in Tampa, Florida. (Photo by Streeter Lecka/Getty Images) /

The Chicago Bears have come a long way from their down period of the past few years. Over that time they’ve endured some of the worst experiences in team history.

No, seriously. It’s been downright awful. If people want to get a proper understand of how desperate this city is to cleanse the pain with a winning season, they merely have to review some of those wish-they-were-forgettable moments. Since this is the summer months and dipping back into the pain seems to be a popular thing to do, why not make it official? Here are the five moments from the past decade Bears fans would consider the absolute worst.

#5:  Ryan-to-Jenkins to set up Elam field goal (2008)

Amidst the avalanche of tough years that have come and gone, most Bears fans don’t remember this moment. However, if one were to bring it up it wouldn’t take long for them to react with utter disgust. The Bears should’ve made the playoffs in 2008. They were good enough to. One could even argue the Jay Cutler trade might not have happened if they’d won this game.

Seriously.

Let’s set the scene. Kyle Orton leads a last-minute drive late on the road against the Atlanta Falcons and caps it with a beautiful 17-yard touchdown pass to Rashied Davis with just 11 seconds left. This gives the Bears a 20-19 lead. Following the kickoff, Atlanta has enough time for just one play.

Inexplicably the defense suffered a break in coverage, allowing Matt Ryan to find Malcolm Jenkins for a 26-yard completion along the sideline. This set up a 48-yard field goal by Jason Elam to win the Falcons the game 22-20. It was a game the Bears should’ve won. Considering they finished 9-7 and one game out of the playoffs, it’s fair to wonder what if they had won.

Would Orton have cemented his place as the starter? The Bears traded for Cutler the following offseason.