Apr 10, 2020 7 min read

What's the best year in Chicago sports history?

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The most glorious year?

Last week I solicited some mailbag questions for Friday’s newsletter. Then Ed Farmer died and I had to push it to the side. Then my plan was to delay the mailbag until today, but I loved one submission so much that I decided to make it the entire email. Running your own newsletter really has its perks, let me tell you.

Anyway, the question comes from #frentofthenewsletter Mike Chamernik:

What was the best calendar year for Chicago sports? What was the worst?

And let's not count 2020, the MJ of bad sports years already.

Thanks for sending that in, Mike.

I’m just going to handle the “best calendar year” for this edition because it’ll take a bit of examination. Plus, let’s be honest: The “worst calendar year” is a great idea for its own newsletter and there might be a few slow days over the next few months when I’ll need that club in my bag.

Best calendar year is a challenging and subjective question. Our five teams have combined for 27 championships over the years, but they’ve probably sprinkled at least twice as many stinkers over the same time. Having them all be successful in the same season is almost an impossibility if you just consider the fact our two baseball teams have only made the same postseason twice in almost 120 seasons of baseball. (The first came when they played in the 1906 World Series well before any of the other three Chicago teams existed; the second came in 2008 when they combined for one lousy LDS win in October.)

So the fact is that whatever answer we come up with, at least one team will probably have experienced a bad season that year. Also, no year has ever featured two titles so picking your best Chicago sports year is somewhat of a Rorschach test over which teams you favor over the others in town.

To get to my answer, I decided I needed to apply some rules to whittle down the choices. Your results may vary, but here is proof of my work.

The year needs to feature a championship

We’re ostensibly all here for the rings, so if a year didn’t end with a parade down LaSalle or a rally in Grant Park, what was the point?

Still, it was hard to eliminate 1984. That was the year the Bears started to rise, the Bulls drafted Michael Jordan and the Cubs made their first postseason in 39 years with Ryne Sandberg winning MVP and Rick Sutcliffe taking a Cy Young. Throw in Walter Payton breaking Jim Brown’s rushing record and DePaul earning a No. 1 seed in the NCAA tournament and it certainly has a case for across-the-board achievement.

In the end, though, the Bears were blanked by the 49ers in the playoffs, the Cubs blew an 0-2 NLCS lead in San Diego and the Blue Demons couldn’t get past Wake Forest in the Sweet 16, losing 73-71 in overtime.

I love Walter Payton, but this is arguably the best moment of 1984 and it’s just not enough for me to crown the year as the best in Chicago sports history.

Don’t take the easy way out and pick 1985*

I know many of your friends and family members have not moved past 1985. Hell, there’s a chance you’ve never moved past 1985. But a vote for those halcyon days would be an admission you just don’t care as much as the other sports. (And again, maybe that’s the case, but it’s not the question that Mike asked me.)

The Hawks did reach the Campbell Conference finals that year and the Chicago Stadium fans did give birth to the cheering the anthem tradition after the team lost the first two games in Edmonton. But they still fell to Gretzky and Co. in the series, 4-2. Meanwhile, both the Cubs (77-84) and Sox (85-77) were middling while the ‘84-’85 Bulls were 41-41 in MJ’s rookie season before His Airness broke his foot in November of 1985.

*Point of clarification: I asked Mike if the Super Bowl victory counted for 1985 or if I had to stick with the strict calendar year and keep it in 1986. He invited me to use my best judgment so I kept it handcuffed to the season that spawned it.

It’s probably not 2005 or 2016

A large portion of fans in this city weren’t happy when the Sox finally won a World Series in 2005. The same thing happened in 2016 when the Cubs broke 108 years of frustration. Malcontents in this city shouldn’t be enough to knock either year from contention, but there isn’t a strong enough second performance to put either over the top. The 2005 Bears were 11-5, but got pantsed by Steve Smith and the Panthers in the playoffs. The 2015-16 Blackhawks were defending Cup champs but dropped a first-round playoff series to the hated Blues and still haven’t won a playoff series since that 2015 run.

If I had to pick between the two? The scale probably tips toward 2005 on the strength of the excitement that Illinois generated in its run to the NCAA final, an MVP-level campaign from Derrek Lee (one of the forgotten great Cubs seasons), a fun Bulls campaign with rookies Ben Gordon, Luol Deng and Andres Nocioni and the 2004-05 NHL lockout sparing us the indignity of a lousy Blackhawks season in front of an empty United Center.

It can’t end with the Bears losing to the Packers in the NFC title game

All apologies to the 2010 Blackhawks and vintage Derrick Rose, but I just can’t do it. Nope.

But it’s OK to pick a year where the Bears were bad

The Bulls, Cubs, Hawks and Sox have all had their share of bad times over the past few decades, but none have routinely disappointed as much as the Bears. So I’m OK not letting them drag down an otherwise good year. Heck, I think I have to be OK with it. (That said, the next Bears Super Bowl win might just elevate that year to the top on its own, just on account of the team going the longest it has ever gone between titles.)

Michael Jordan needs to be involved

I was wondering what to do with all eight of the Bears’ NFL championships considering all came before the Bulls were even established as a franchise. Luckily, I decided there’s no way to have Michael Jordan call your city home for 13 seasons and not pick at least one of those years we were lucky to watch him up close each night.

So that eliminated eight of the nine Bears title seasons, four of the city’s World Series crowns (all of which came before Prohibition) and all six of the Hawks’ Stanley Cups.

It also gives you an idea of where I ended up.

And the answer is …

1993

Do I love the pick? Nope.

But I’m OK with it.

As I said, there’s going to be problems with any year. We could pick the ‘85 Bears or 72-win Bulls in 1996, but that’s just picking the greatest season and not considering the performance of the other franchises.

In 1993, we had …

• The Bulls finishing off their three-peat with a great series against the Suns and John Paxson’s last-second shot. (Is it OK to go back to liking him yet?)

• Both baseball teams finishing over .500, something that has only happened 25 times since 1901. The Cubs went 84-78 as Sammy Sosa broke out with 33 home runs in his first big season.

• The White Sox winning the AL West with 94 victories. Frank Thomas won AL MVP, Jack McDowell won AL Cy Young and Bo Jackson won Comeback Player of the Year.

• The Blackhawks winning the Norris Division with 106 points. While they were swept by the Blues in the first round of the playoffs, there was the release of the iconic NHL ‘94 in October 1993 to help soften the blow.

• Notre Dame beating Florida State in November 1993 in the “Game of the Century.”

• Rookie of the Year and Rudy were released (as was The Fugitive … good year for movies with Chicago ties).

• Anthony Davis was born in Chicago on March 11, 1993.

Does 1993 top 1992 (Bulls title + Hawks run to Stanley Cup final) or 1998 (Bulls final title + the McGwire/Sosa home run chase)? I think you could make good arguments for any of the three, but the breadth of 1993’s high points — save for the Bears 7-9 finish — is what puts it over the top.

As for that last AD fact? Yes, I’m banking on it solidifying my case for 1993 once Anthony Davis returns to his hometown and puts another banner in the United Center’s rafters.

Hopefully in a year when the Bears also win the Super Bowl and then this entire exercise is reduced to a much easier choice.

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Bob Verdi on former Blackhawks captain Pat Stapleton, who died this week at age 79. (Chicago Blackhawks)

Ricky O’Donnell on four things Arturas Karnisovas should do with the Bulls. (BlogABull)

Jon Greenberg on the Bulls’ flawed search leading to a promising leader. (The Athletic)

• These were … not great.

• Not a Chicago link, but the best thing I read all week: How Kobe Bryant’s death brought Bobby McIlvaine back to life. (Philadelphia Inquirer)

• Finally:

And that’s it for this week. Hopefully another week closer back to being normal. As always, thank you for being a #frentofthenewsletter. Enjoy your weekend.

Kevin Kaduk
Kevin Kaduk
Kevin is the founder of Midway Minute.

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