Jerry plays politics

It’s been five days since we had a White Sox game on TV, so let’s do what we usually do when there’s little to talk about and complain about team ownership.

We love to grumble about Jerry Reinsdorf, largely because he’s managed to oversee a total of six playoff appearances in 40 years of White Sox ownership. His tenure in Chicago in multiple sports has been by and large a failure when Michael Jordan isn’t involved.

But! What if I told you that not only has his unwillingness to spend quite enough prevented both of his teams from achieving any kind of sustained success over the last two decades, the money he has invested in the real world has been at best less-than-promising and at worst downright ghoulish and disgusting?

Above all us, Jerry is a wealthy businessman. Generally speaking, wealthy businessmen like to play politics. In Chicago? It’s damn near impossible to become and continue to be a wealthy businessman if you don’t play politics.

Playing politics requires some money — money that leaves a public record when it changes hands (most of the time). In debates about spending on the White Sox, a line sometimes emerges that paints the team as having negative (or neutral, at best) operating revenue. “The team doesn’t make money,” it goes.

Even if that were true — and it isn’t — you sure can’t say the same about the Bulls. In any case, it might not mean much next to a team’s payroll, but the $1.8 million and more in political campaign donations Reinsdorf has made over the past quarter-century isn’t exactly chump change, either. And while that sum might not compare to even an average baseball player’s salary, one would think that he’s not spending money not to make money. Political money isn’t a one-way street, if anything’s for sure.

Rich team owners always spread their money around. While the White Sox have descended into disarray over the past decade, Reinsdorf’s endeavors in the political field don’t make one feel much better about it. We can start with the hot topic: The Mayor’s race. While he sat out Lori Lightfoot’s election, he would not be so inert this time around: Over the last year, the Reinsdorf family contributed $40,000 to the now-outgoing mayor’s re-election campaign. Woof. His $58,500 investment in Rahm Emanuel between 2011 and 2015 probably paid better dividends. Probably not good for the rest of us!

That’s relatively chump change in the grand scheme of things, but we’ll get to the big bucks in a moment. On the state level, Reinsdorf has taken some small Ws, throwing a cool $5,000 to now-Governor Pritzker’s campaign a month before his election in 2018. That’s probably a whole day game’s revenue at the concession stand formerly known as Goose Island! A little more substantial was the $58,000 he spent to get Pritzker’s predecessor Bruce Rauner elected. Remember those couple of years where Illinois straight-up didn’t have a budget? That was fun.

He’s taken still-bigger swings than that. In 2017, Reinsdorf stuck $200,000 in the campaign coffers of former West suburban congressman Dan Lipinski, a Democrat whose opposition to abortion and marriage equality ultimately led to a primary loss to in 2020. In the election cycle following the donation, however, Lipinski defeated his primary challenger, future Congresswoman Marie Newman, by a 51-49 margin. Hey, how much money, exactly, was that fight with Lucas Giolito about last spring?

The money goes far and wide, national and local: $5,000 increments to Senate candidates across the country, primarily Republican incumbents, and to the Alderman with jurisdiction over the United Center. That’s all on top of the $800,000+ donated to broader Political Action Committees (PACs) supporting candidates of all sorts. He recently dropped a cool 20G on Fritz Kaegi’s campaign for Cook County Assessor, too. Getting on the same page as the guy in charge of property taxes probably seems like a pretty neat idea when you run a baseball stadium and one of the country’s bigger basketball arenas.

All of this is completely par for the course in this city, country, society, etc. This is what you do at that level of business and wealth. Look on the other side of town and you’ll see things infinitely more insidious, from a far more powerful ownership group. Ricketts money and power has spread its tentacles nationwide, but Jerry remains by and large a local power player — he did show up in Mayor Lightfoot’s leaked text messages, after all! — who dabbles elsewhere. That doesn’t mean it’s any prettier. Reinsdorf might not be throwing around tens of millions, but the characters in those donation logs aren’t any more savory. But hey, if $15 Bud Lights, $10 pizza slices, and a 256-tier ticket price pyramid are what I have to suffer so that the owner can scrape up enough change to send $10,000 to Senate candidates who call for special legislative sessions to implement a total abortion ban, who am I to question it? The White Sox might be falling apart, but at least he’s supporting winners somewhere, right?