What’s the worst year in Chicago sports?

So, things are pretty bleak right now on the Chicago sports scene. The Sox are terrible. The Bulls are stuck in limbo. The Bears — well, the less said right now the better. The Blackhawks have a potential superstar, but the stench of the old regime still taints everything, leaving a tacky taste in the mouth. The Sky still have Kahleah Copper, which is awesome, but they’ve been lapped by the Aces and the Liberty. The Cubs had been playing good fun baseball, but they’ll be just as idle in October as the White Sox.

But you’re reading a blog about the White Sox. You’re reading it on October 1. Obviously, you aren’t one of those people who just “roots for Chicago!” Even though I gave you permission to not hate the Cubs, chances are our Crosstown rivals being 20 wins better doesn’t fill you with joy.

So this is bleak. I am not the only White Sox/Bears fan to question why we do this, why we put up with such misery on a constant basis.

But then, I’m old. I’ve had many years where caring about sports just seemed to make no sense whatsoever. So here are a few years that pop up as the worst of my lifetime. I chose these mostly from memory, so please comment about years that were worse.

A few notes:

1. While the Sox were largely terrible throughout the 80s, the Bears were always seemingly in contention and the Bulls were ascendant, and anyway had a burgeoning superstar, so it was hard to pick much from that decade
2. I am just choosing the “Big 5”. My knowledge of soccer and the Sky is too limited for me to comment intelligently on them. This is a very subjective list.
3. I’m trying to take this objectively, as Chicago as a whole, not just a “bitter White Sox” list, which is why 1998 isn’t on it.
4. We want to avoid teleology, and remember the year as it felt then, not “but we were about to turn a corner!”

1987

Chicago Bears: 11-4 (NFL had a strike-shortened season with 15 games)
Chicago Blackhawks: 29-37-14
Chicago White Sox: 77-85
Chicago Bulls: 40-42
Chicago Cubs: 76-85
The Cubs were garbage. The White Sox were garbage. The Hawks were years away from having their dynamic early-90s teams. The Bulls were getting better but were frustrating, miles behind the dominant teams of the era. But the Bears were good, right! Got a No. 2 seed?

On paper, yeah. But this was the strike year. It started with acrimony. The league allowed scabs, and Mike Ditka, a true shithead company man, backed management to the hilt, calling the “spare Bears” his “real players.” A team that had been feuding since winning the Super Bowl was truly dissolving. While the Bears were too talented not to win a lot, they were angry and no fun, and lost to Washington in the playoffs. This was Walter Payton’s final game, and I remember going outside afterward and crying at the injustice of him going out like this. Goddamn, I loved Walter.

1995

Chicago Bears: 9-7
Chicago Blackhawks: 24-19-5 (Shortened NHL season due to a lockout)
Chicago White Sox: 68-76 (Shortened MLB season due to a strike)
Chicago Bulls: 47-35 (Remember, Michael Jordan returned late in this season)
Chicago Cubs: 73-71
You might be asking: Why not 1994? After all, the Sox had their best team of the decade, robbed of the World Series due to the owner’s refusing the budge on reasonable profit sharing. But the Bulls were good that year despite the loss of MJ, and the Hawks were still feisty, before the NHL lockout.

A year later everything changed. The Sox couldn’t pull out of the post-strike funk. The Hawks run of good teams started to sputter. The Bulls were middling before MJ came back, and while that was one of the most exciting things ever, the playoff sputter left us to wonder if the magic was really gone; that this would prove to be a ridiculous fear didn’t make it any less real at the time.

The Bears were 9-7, but that came after a 6-2 start. They drafted Rashaan Salaam. You could feel the Wannstedt era going off the rails.

1999

Chicago Bears: 6-10
Chicago Blackhawks: 29-41-12
Chicago White Sox: 75-86
Chicago Bulls: 13-37 (Shortened NBA season due to a lockout)
Chicago Cubs: 67-95

I feel like this has to be the winner. While the 1998 Bears were dreadful, it was fun that Wannstedt got fired. And the 1999 Bears were far from good. It was a boring, pointless season that made the good old days seem farther and farther away. The Sox and the Cubs were both bad and boring, the Cubs squandering all the goodwill that came from their unexpectedly great 1998 season. I certainly had no real inkling that the Sox were going to win their division the next year.

The Blackhawks were very bad. Doug Gilmour was the captain. Eric Daze was on the team. We were a few years from Alexander Karpovtsev, but it felt tilting toward that way. Indeed, the whole franchise felt like it was sliding toward irrelevance.

And the Bulls? Oh my god. Not only did they start 2-26, but they traded Toni Kukoc in a deal that got us John fucking Starks. If there was a more clear way to say “the dynasty is dead and buried” I couldn’t imagine it.

Everything in Chicago sports seemed like it was collapsing. I prayed for Y2K to end it all.

2002

Chicago Bears: 4-12
Chicago Blackhawks: 30-33-13-6 (Before the NHL moved to a straight W-L-OTL format)
Chicago White Sox: 81-81
Chicago Bulls: 21-61
Chicago Cubs: 67-95

Oh man, this year. For starters, the Cubs were terrible and the Hawks were pointless and nobody watched them. The Bulls were expected to be better, with Jalen Rose and Donyell Marshall being signed, and Jay Williams being drafted. But they were never good. It was clear Jerry Krause was never going to successfully rebuild.

The Sox had another “we’re good, no, let’s fade” type of year, as the magic of 2000 continued to recede in a long and ultimately boring summer.

And the Bears? Remember 2001? That was awesome! But the season spent in Champaign was a terrible slog, as all the breaks they caught in 2001 disappeared under the weight of poor play and worse coaching. 2001 was the year all my friends and I finished college, and we watched all the games with giddy joy, in the basement of my parents’ house, making the trek to the suburbs every Sunday, spending time with my dad and brothers. It started a tradition.

And yeah, 2002 made sure that the tradition involved morbid jokes and endless frustrations.

2019

Chicago Bears: 8-8 (They did not make the playoffs this season.)
Chicago Blackhawks: 32-30-8 (They missed the playoffs this season.)
Chicago White Sox: 72-89
Chicago Bulls: 22-43
Chicago Cubs: 84-78 (The Cubs did not qualify for the playoffs in 2019.)

In 2018, the Bears were good and got double-doinked. Still, the Bears were good, and we were excited. Then the season started with a 10-3 loss to Green Bay that seemed clinically designed to remove any excitement or fun. While they were 3-1 at one point, they never seemed good, and an 8-8 season made us all question if Nagy forgot how to coach. He seemed transformed from fun and progressive to completely spooked, all by the cruel bounce of a field goal.

The Bulls were nothing, but that was normal. The Cubs missed the playoffs, and you could feel the core crumbling. The Hawks missed the playoffs for the second straight year, and you knew the good times were over.

The Sox made a run near the All-Star break that gave you hope for the rebuild, but the second half of the season was brutal and boring. Not a lot to cheer about.

So there are some candidates. It’s too early to say 2023 will be up there, but it certainly has a shot.

What are your thoughts? What did I miss?