#1: 1986 Bears
Without question the most disappointing team in Chicago sports history. Everybody remembers how dominant the 1985 Bears were. Going 15-1 and winning the Super Bowl. Well expectations were they would do it again in 1986. Their defense set the NFL record for fewest points allowed in the regular season at that point (187). They finished with a 14-2 record, also best in the league. It looked like nothing would stop them.
Then the Washington Redskins, a team that has long loved raining on Chicago’s parade over the years, stunned the football world with a 27-13 victory at Soldier Field. It was a dream-shattering event. That was supposed to be the year the Bears would be validated as one of the greatest teams in history. Not only were they beaten on their own turf, but soundly beaten. It’s a loss fans still remember and can’t get over 31 years later.
