In Chicago, waiting for the owner to die is a long-standing tradition

Jerry Reinsdorf is 84.
Jerry Reinsdorf is 84.
Photo: (Getty Images)

In the aftermath of the revelation that Jerry Reinsdorf knowingly hired Tony La Russa the day after the latter was charged with a second DUI, a lot of people not as familiar with Reinsdorf’s ways are wondering how such a thing could happen. You have to understand that Reinsdorf works in his own unique way.


Reinsdorf is not Bob Nutting, or Jeffrey Loria, or the Wilpons, or half a dozen other vampire squids who are/were only around to grift fans and make money and never care or just be so incompetent the whole ship went down regardless. Reinsdorf does care, just in a completely skewed and damaging way.

That doesn’t mean Reinsdorf doesn’t like to save a nickel wherever he can. This is the man who spearheaded the 1994 strike that canceled a World Series, after all, in order to try and break the players’ union. And he is the one who has instructed both of his front offices, White Sox and Bulls, to always get the best deal instead of the best player. It’s why neither has signed a preeminent free agent in a decade or two. It’s why Manny Machado isn’t on the South Side, it’s why the Bulls haven’t had a player anyone outside of Chicago can name in eons that wasn’t Derrick Rose or Jimmy Butler. And it’s worth noting that both of those guys, their best players over the past 20 years, moved on under cantankerous circumstances.

But Reinsdorf cares about people, or more accurately, his people. He’s always trying to right wrongs from the past. In some cases, that’s actually a good thing. It’s why Jerry Krause has a banner above the United Center, even though he is still reviled by a large swath of the city despite being the architect of the most successful team the city has ever seen in its sporting history. Guys like Randy Brown were given jobs when they really needed them.

But it also leads to the myopia that’s been on full and hilarious/confounding display these past couple weeks with the La Russa hiring and fallout. It’s why Robin Ventura was kept in a manager’s job he didn’t even really want for years. It’s why Kenny Williams kept as an influential voice in the front office even after being removed from the GM chair after he had blown up the entire organization. It’s why Reinsdorf sided with Krause over Phil Jackson and Michael Jordan, because the latter two bitched about A) Reinsdorf’s guy and B) money. Those are no-no’s in Jerry’s world. It’s why you might have stared on in awe while Reinsdorf talked about the schism in the Bulls organization during “The Last Dance,” as if it was all in the third person and he wasn’t, y’know, THE FUCKING BOSS. John Paxson was allowed to turn the Bulls into that car you see on the side of a country road that has nothing under the hood. He was Jerry’s guy, and he kept Jerry’s team pretty cheap.

Speaking of the wayback machine, La Russa was fired by the White Sox 34 years ago because another one of Reinsdorf’s guys, Ken Harrelson, was an absolute buffoon. And Reinsdorf has wanted to make it up to La Russa ever since. Because, again, he cares — in his own way.

All of it has left Sox fans staring in a stupor at what they’ve been forced to digest much like Bulls fans. (I guess you can’t really stare at something you’ve digested and wouldn’t want to if you could but just go with me here.) Because that’s how it goes in this town.


Perhaps Chicago’s collection of owners past and present isn’t worse than many other places. But as a resident, it sure feels like it. It’s long been assumed that nothing will truly change with the Sox for sure, and the Bulls possibly (though they may already be with their offseason moves in the front office), until Jerry hands off the reins. Which he won’t do until he spins off this mortal coil.

And that’s the tradition around here. The Blackhawks were under the find-the-rocks stewardship of Bill Wirtz for decades, who turned perhaps the country’s most loyal and passionate fanbase away until it was nothing but dust through some of the most archaic policies known to man. He kicked off in 2007, and within a year the Hawks were on one of the more successful runs in the NHL and by far the best the organization has ever seen.


The Bears have been in the McCaskey/Halas family for their entire existence. They have one championship in the Super Bowl era. And every organizational realignment is doomed by the fact that is being spearheaded by the McCaskeys, as their cluelessness and ham-handedness with everything has seen a parade of doofus presidents, GMs and coaches. They never get it right, because the league passed them by decades ago.

The Cubs seemed doomed when owned by the Tribune company, which in its own way suffered a death that saw the Cubs sold off, which brought about their first World Series title in 108 years. Of course, since that World Series, Cubs fans are back to wishing their owner would die simply because he’s such a raging asshole. Still, getting out from the grips of the Tribune company ushered in, eventually, the club’s most successful run.


And that’s how it goes here, the resignation that not much will change or move into the current age until the one in the biggest suite crosses the rainbow bridge. Because none of these owners will ever sell. The Bears are all the McCaskeys have.

We pass it down from generation to generation. I can’t tell you how many Hawks’ fans first words were, “Fuckin’ Wirtz.” Many a Miller Lite in South Side taverns have been tilted back with the soundtrack, “Goddammit, Reinsdorf.” The only thing that brings this city together entirely is throwing up our arms whenever a McCaskey says or does anything. It’s all we’ll ever agree on.


Wanna know why we’re so fat? We’ve been eating our feelings for decades.

We can't be too careful. Two guys in an airport...talking? It's a little fishy.