Chicago Bears: The 10 Most Heartbreaking Moments in Team History

As Bears fans know, this is a team with a long and storied history. Their original owner and coach, Papa Bear George Halas, practically invented the sport when he "thrilled the nation with the T-formation..."

But as Bears fans also know all too well, there have been plenty of disappointing times in our history. From games that should have been won, and to the sad, sad ending to the all-too-brief life of the greatest Bear ever, the tears will sometimes flow like lava down the side of a volcano.

The emotions are often just as raw.

So grab a tissue and re-live these 10 moments in Bears history when all was not so rosy. And feel free to add remembrances of your own personal angst from your years as fans of the Monsters of the Midway.

10. Bears Stunned in 1942 Championship Game

I'm sure we all remember this like it was yesterday!

Following an historic 73-0 win over the Washington Redskins in the NFL Championship in 1940, and winning a consecutive championship the following year, the Bears once again found themselves facing the Redskins in the 1942 NFL Championship.

However, this time the Redskins stun the Bears 14-6 to spoil their undefeated season and prevent a third straight title.

Now, I'm old but I'm not old enough to feel the sting of this loss. However, let's assume that it was painful for Bears fans to watch.

9. 49'ers Blank Bears in 1984 NFC Championship Game

The Bears were on the cusp of a championship season but Bears fans didn't know that when we watched this game.

That season, Payton broke Jim Brown's record for NFL rushing yardage, and the Bears went 10-6 to earn their first division crown in 21 years.

The Bears beat the Redskins in the first round of the playoffs but were shut out by San Francisco 23-0 in the NFC Championship game.

It was a disappointing way to end a terrific season.

8. Miami Spoils Bears Chance at Unbeaten Season

The 1985 season was a magical one for the Bears, though the disappointment over losing to the Miami Dolphins on a Monday night still rings loudly for many fans.

The Bears were a perfect 12-0 when they travelled to Miami on December 2, 1985. Dan Marino may have never won a title, but he riddled the Bears defense that night, and the Bears fell 38-24.

Watching the 1972 Dolphins on the sideline celebrating was tough to see. The game featured a fight between Ditka and Buddy Ryan, which almost came to blows.

Miami was the only team that season to exploit the vaunted "46" defense. It was the only loss in a 15-1 season for the Bears.

7. Walter Payton Fails to Score a TD in Super Bowl XX

That great season's only blemish, other than the Monday night loss to Miami, was the heartbreaking scene where Payton sits dejected on the sideline after he fails to score a touchdown despite a 46-10 victory.

That William Perry scored a touchdown in the game makes this an even more egregious mistake on the part of the Bears.

Mike Ditka has said that failing to get Walter a TD in this game was one of his biggest regrets.

6. Bears Lose to Packers in NFC Championship Game

Jonathan Daniel/Getty Images

CHICAGO, IL - JANUARY 23: Quarterback Jay Cutler #6 of the Chicago Bears reacts in the second quarter against the Green Bay Packers in the NFC Championship Game at Soldier Field on January 23, 2011 in Chicago, Illinois. (Photo by Jonathan Daniel/Getty I

Ah, it's the one that's most fresh in our memories and the pain still stings like it was yesterday. That the loss came at the hands of the hated Green Bay Packers makes this one hurt a little bit more.

2010 was a surprisingly good year for the Bears, and while they split two games with the Pack during the regular season, the fact that the Bears were playing at home seemed to make it very plausible that the team was going back to the Super Bowl.

That was not to be, and the way it happened was perhaps as heartbreaking as the end result. QB Jay Cutler went out with an injury, which resulted in much controversy over whether he was really hurt or not by fools that were eventually proven wrong.

Still, the loss was tough to take.

5. 1st Round Playoff Loss in 1986

The Bears had come off one of the most impressive Super Bowl runs in NFL history the year before, so despite injuries to Jim McMahon and the loss of defensive coordinator, Buddy Ryan, Bears fans like myself were shocked beyond disbelief when the team went out in the first round of the playoffs.

The Bears defense was even stronger, at least statistically, following their Super Bowl win as they established a new NFL record low for points allowed (187) and they won the NFC Central title with an impressive 14-2 record.

Despite all that, the Washington Redskins beat the Bears 27-13 at Solider Field in the first round of the playoffs.  

That it was a cheap shot from Packers idiot Charles Martin that injured McMahon makes this loss even more heartbreaking to Bears fans.

4. Bears Lose to Colts in Super Bowl XLI

The game started so promising for the Bears as Devin Hester returned the opening kick 92 yards for a touchdown. But the ending was not nearly as good.

The Bears led 14-6 after the first quarter and Bears fans dreamed of the first championship since January of 1986. But it wasn't meant to be, as the Colts won Super Bowl XLI 29-17.

Lovie Smith and Tony Dungy became the first black head coaches in Super Bowl history. Unfortunately, Smith also became the first black head coach to lose a Super Bowl game.

3. The Brian Piccolo Story

Come on, admit it, we've all shed some tears while watching Brian's Song. 

Piccolo played for the Bears for four seasons and was a close friend of Gale Sayers. He died from from embryonal cell carcinoma, a germ cell tumor.

Of course, they made a movie of his story, focusing on the relationship between Sayers and Piccolo. It starred James Caan as Brian Piccolo and Billy Dee Williams as Gale Sayers.

It was definitely a box of tissues kind of movie. His life was much too short as he died at 27.

2. Dave Duerson Commits Suicide

It seems almost disrespectful to reduce the life of a man and former Bears player to a list in a slideshow. But as the events have unfolded, the story becomes even more tragic by the moment.

Duerson was, by most accounts, a kind and caring and intelligent man. He was smart enough to recognize that he may have been starting to show symptoms of Chronic Traumatic Encephalopathy‎, thanks to a cause he had been personally involved with over the years.

CTE is believed to be caused by repeated blows to the head. The former Bear had complained of memory loss and difficulties with spelling words.

That he shot himself in the chest to save his head from damage, so that his brain could be used for research, shows his commitment to the cause and that he wanted his death to help others going forward. 

That Duerson took his own life at just 50 is very painful indeed.

1. The Tragic Passing of a Bears Legend

Walter Payton, aka, "Sweetness", as he was known to his teammates and adoring fans, died at age 45 of a rare liver disease in 1999.

Walter was simply the greatest football player the Bears ever saw, and one of the best in NFL history. When he retired as an active player, he owned the record for rushing yards, touchdowns, carries, yards from scrimmage, all-purpose yards and many other categories.

But his legendary runs, where he would deliver punishing forearms to would-be tacklers and the way he would pop right back up after a hit, were even more special than his stats. His workouts, which included grueling climbs up a steep hill, were legendary as well.

Coach Mike Ditka, never a man for sentiment, described Walter as the greatest player he ever saw and an even greater human being.

Payton's legacy continues through the charitable Walter and Connie Payton Foundation.

That he was taken from us at such a young age is the most tragic thing to ever happen to the Chicago Bears family.