Here's a tough one, if only due to the depressingly large amount of choices - what is your most painful Bears moment? Chris Conte at the end of the Packers at Bears game in 2013 was the first thought that came into my mind, but I look at that moment as more of a mercy killing of a horrible Bears defense than something truly painful. You could take any number of injuries to players in the middle of promising seasons, but I can't think of any that were so tough as to top this list. There are also plenty of decisions made by the front office, which in recent history could range from not bringing back Brian Urlacher to not firing Mel Tucker.
It's hard to top the pain of a single game-defining moment for any sports fan, however. And when it comes to painful single plays, it's even harder to top the Rex Grossman interception to Bob Sanders in the second half of Super Bowl XLI. Devin Hester had my hopes high at the start of that game, and with the Colts special teams spotting Grossman a touchdown, you figured the Bears had a puncher's chance even into the second half. Enter "Bad" Rex Grossman, and goodbye Super Bowl chances. While Brian Urlacher was able to pull a win against much greater odds against Arizona in that 2006 season, Peyton Manning is no Matt Leinhart: you just knew the game was over the second Grossman threw that INT.
So, WCG, what is your most painful moment in your Bears fandom?