Sports run the gamut of emotion, delighting and destroying the human spirit. In honor of the latter—and grief-stricken sports fans everywhere—we present Sad Sports, Volume 1: Chicago.
This inaugural compilation of sorrow is written by our very own Joe Wolff, who takes us on a journey through the eyes of a sad Chicago sports fan. May another person’s misery bring you joy on this day!
I recall this starting as a joke in one of our meetings, but apparently no one was concerned about the emotional turmoil I would have to put myself through (again) in order to revisit these past miseries, so here we are.
With the help of Shutterstock’s editorial library, I’m happy to report that I was incredibly successful in making myself unhappy fast.
Two caveats before we dive into the darkness:
- Yes, there are plenty of other sad moments in Chicago sports history, as I’m sure there are for any city. Sports are visceral, though, so my rule in compiling this shortlist was simple: I had to be alive (and capable of retaining memories) when each moment occurred.
- Baseball divides Chicago. I am a Chicago Cubs fan, which aside from being an incredibly masochistic allegiance, means I do not support activities carried out by the Chicago White Sox (who, ironically, have perhaps the darkest moment in Chicago sporting history when they rigged a World Series in 1919). Still, any inclusion of them here would’ve been done in jest, so they have not been considered.
Now, let’s get sad.
The Sadness Scale
To help instill order within the chaos, I’ve developed The Sadness Scale. It ranges from “Bittersweet” (mild sadness) to “What did I do?” (ultimate grief). Each moment below represents one of these tiers.
So, without further ado . . .
5 Moments That Broke Chicago
1. Michael Jordan Retires (Again)
Sadness level: Bittersweet
After winning his sixth championship, Michael Jordan announced his retirement—again—from the NBA. Why again? Because Jordan kinda-sorta retired from basketball at the start of the 1993 season, coming off of his third straight championship.
His father had passed, and Jordan decided to give baseball a shot. He would play in the Chicago White Sox organization for two years before coming back to the NBA.
In 2001, Jordan would un-retire for a second time and lend his (still impressive) talents to the Washington Wizards for a few years. But, his retirement from the Bulls marked the end of an era. There have been little pockets of success for the team since, but nothing quite like the days of Magic Mike.
2. Indianapolis Colts 29, Chicago Bears 17
Sadness level: Devastation
Generally, I agree with Andy Dufresne in The Shawshank Redemption when he tells Red: “. . . hope is a good thing, maybe the best of things, and no good thing ever dies.”
Except here. Hope flatlined.
The images above tell a story of one quarter. An opening kickoff return by special teams stud Devin Hester . . . two Colts’ turnovers . . . a Bears touchdown from Rex Grossman to Muhsin Muhammad . . .
. . . and yet . . .
. . . that’s a lot of Indiana blue getting the celebratory Gatorade bath at the end.
Losing a matchup like this is an almost too-easy “Sad Sports” moment, but the Bears are a special organization, capable of turning a mild cardiac arrhythmia into a full-on heart attack.
A strong first quarter slowly devolved into devastation and gut-wrenching pain.
It was unpleasant.
3. 4th and 8
Sadness level: Rage Sadness
Every fan hits this level at some point in the season, no matter the fan, no matter the sport. It’s impossible not to.
Rage Sadness is equal parts grief and seething anger, usually the result of a game’s outcome and, on a more granular level, a specific play in said game.
Like, say, if your team happened to be playing its biggest rival in the last game of the season with the winner advancing to the playoffs. In this totally made-up scenario, your team managed to be ahead 29-28 with :46 seconds left and had the other team pinned near midfield with a 4th and 8 ahead of them.
Again, fictional example.
Then, inexplicable reasons, your team’s secondary decided not to cover someone (who, for the example’s sake, let’s pretend is named Randall Cobb and plays for the Green Bay Packers), resulting in a 50+ yard game-winning touchdown, officially eliminating the Chicago Bea—your team—from the postseason.
Fun.
4. The Double Doink
Sadness level: All Hope Is Lost
The Double Doink is a moment already so ingrained in Chicago’s collective nightmares that it’s why the Bears get one more spot on this list.
2018. Chicago made the playoffs for the first time in eight years. Head coach Matt Nagy, in his first year with the team, looked like he might be the answer the Bears had been searching for.
Then this happened. Kicker Cody Parkey had a chance to win the game with a 43-yard field goal. The kick was tipped, hit the left upright, then bounced off the crossbar and into the end zone.
Chris Collingsworth, who was announcing the game with Al Michaels, put it best: “Oh my goodness . . . the Bears’ season’s gonna end on a double doink.”
So did my soul.
5. No Cubs No – October 14, 2003
Sadness level: What Did I Do?
Alas, there are moments in sports fandom that are so heartbreaking, they make you question what actions of yours could have possibly contributed to the outcome. Lots of time spent in front of the mirror, asking that person looking back . . . ”What did I do?”
Before the 2016 Cubs were celebrating an end to their historic 108-year World Series drought curse, there was pain. Lots of it. That dangerous, all-too-familiar feeling prevailed in 2003 . . .
. . . hope.
Even casual sports fans with no rooting interest in the Chicago Cubs know this story. There was a ball flying toward the stands late in Game 6 of the National League Championship Series. There was a man—Steve Bartman—who reached out for that ball. The rest is history.
The Cubs would lose this game and then lose Game 7, successfully becoming (at the time) only the 4th team in Major League Baseball history to blow a 3-1 NLCS lead.
Let’s be real though—Moisés Alou was not going to catch that ball, and I want to make it very clear that I do not support the outrage that circled around this poor baseball fan who was simply sticking a reactionary hand out toward a fly-ball . . . like the twelve other people around him.
Should you wish to further unpack one of the saddest moments in Chicago sports history and explore how fandom can quickly descend into fervent irrationality, check out the ESPN 30 for 30, Catching Hell.
As for the baseball that Bartman reached out for, it was (of course) deemed cursed because that’s what happens when your team has gone 100+ years without winning and you desperately need an answer for that elusive, extra-voweled question, “Whyyyyy?”
The Harry Caray Restaurant in downtown Chicago purchased the ball for almost $114,000, displayed it for a few weeks, and then blew it up.
This actually happened.
Unlike the baseball, Bartman’s seat still exists in Wrigley for fans to sit in. And, Bartman himself was presented with a World Series ring after the Cubs won in 2016.
It’s Not All Doom and Gloom
The Cubs’ 2016 World Series victory was the greatest sports moment in my life so far. I stood outside Wrigley, wondering alongside thousands of other fans, “Is this really about to happen?”
It was an incredible experience, and that’s the real beauty of sports. We connect with these teams and players because they represent a piece of us. Our cities. Our hometowns. Our states. There are years when they’ll obliterate our fandom, but they make the years of dominance—or even mere surprise—that much better.
It’s fun to bemoan the failures because it’s even more fun to celebrate the victories. I’ve been fortunate to be alive for a historic run by the Chicago Bulls in the ‘90s (even if I was relatively young for most of it). The fact that the Bears have even made a Super Bowl in my lifetime is not something every fan can say. Then there’s the Chicago Blackhawks—Stanley Cup champions in 2010, 2013, and 2015.
In the end, if you’re going to proudly flaunt your team’s gear when they’re tearing through opponents night after night or week after week then, like it or not, you must sport those same jerseys and hats and jackets when they’re making you sad.
Oh so sad.
About Shutterstock’s Editorial Collection
Good news, folks—Shutterstock’s editorial collection is not oh so sad. It’s a place for live access to news, sports, and entertainment images, including (as you’ve seen here) a vast library of archival photos.
Editorial content can be used in news articles, non-fiction books, documentaries, and other newsworthy purposes. Beyond their functionality, these images serve a larger purpose, reminding us of the past, informing us of the present, and helping us prepare for the future.
**Sad Sports will return.**
Cover image via Nam Y Huh/AP/Shutterstock.
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