Chicago Bears: 5 most haunting moments of Super Bowl era

CHICAGO, IL - DECEMBER 29: Randall Cobb #18 of the Green Bay Packers reacts after catching the game winning catch during the fourth quarter against the Chicago Bears defends him on December 29, 2013 at Soldier Field in Chicago, Illinois. The Green Bay Packers defeated the Chicago Bears 33-28. (Photo by David Banks/Getty Images)
CHICAGO, IL - DECEMBER 29: Randall Cobb #18 of the Green Bay Packers reacts after catching the game winning catch during the fourth quarter against the Chicago Bears defends him on December 29, 2013 at Soldier Field in Chicago, Illinois. The Green Bay Packers defeated the Chicago Bears 33-28. (Photo by David Banks/Getty Images) /
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The Chicago Bears have had a lot of memorable Halloween moments, but that doesn’t quite capture the true depth of the word “haunting.”

Those types of moments are reserved for what the holiday represents. Giving people nightmares they wake up at times in a cold sweat from. Bears fans have experienced plenty of those over the many years since the Super Bowl era began in 1967. Most of them in just the past two decades. That’s how fresh some of the wounds still are.

The question is amidst the many moments of heartbreaking disappointment, which were the absolute worst? It took some serious deliberation, but here are five that stood out the most for their impact, short-term and long-term, as well as the deep wounds they’ve left behind to this day. They say everybody is entitled to one good scare on Halloween.

Maybe this is a bit much.

#5: Darrell Green punt return

Most Bears fans probably don’t remember this play as much as others on the list. Understandable since it took place more years ago than any others. That said, it’s easy to forget how backbreaking it was. The Bears and Washington Redskins were deadlocked at 14-14 in the divisional round. It was in Chicago and both sides were kind of slugging it out.

It was then in the 3rd quarter that cornerback Darrell Green, nursing injured ribs and all, completed the only punt return touchdown of his NFL career to put Washington up 21-14. The Redskins would win 21-17 and go on to win the Super Bowl. The reason this is so painful is that the odds of the Bears winning it that year were ideal.

Their opponent in the NFC championship would’ve been the Minnesota Vikings, a team they’d swept during the regular season. Then they would’ve played the Denver Broncos in the Super Bowl, a team notorious at that time for big-game collapses. A gigantic missed opportunity.