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Grading the White Sox: Jerry Reinsdorf

When team ownership is more job than dream

At midseason, the SSS staff graded the 46-46 White Sox, from the head of the class Dylan Cease down to Dallas Keuchel. We invented a WARsss metric that could very well be just a cute way to trot out our special site grades — but really for all you know could be the product of years of research in a stats lab.

Our expanded report card will take us through everyone who saw time in uniform for the White Sox, plus some front-office types. Most of our writers will take on a couple of players, with final grades and short writeups, running through the end of November. Enjoy!

Jerry Reinsdorf
Midseason: -1.2 sssWAR
Final: -2.321 sssWAR

In 1978, the Supreme Court ruled on an arcane tax and ownership case involving depreciation, deductions, and other issues that only tax aficionados and investors care about. Put most simply, the case, Frank Lyon Co vs the United States allowed people who leased real estate to get some tax benefits, by deferring something or deducting something else. Again, only tax hounds and other people too dull for even David Foster Wallace paid attention to it.

One of those people was Jerry Reinsdorf, a young Brooklyn kid transplanted to Chicago, who rose from a small-time tax analyst to a smart investor. Frank Lyon changed the rules of real estate, and made him a fortune. It even earned him enough to purchase, for $19 million, the Chicago White Sox, a run-down team of miscreants on the unloved side of town.

And that’s why we watched Bryce Harper lead some other team into the World Series.

Of all the years that Reinsdorf has owned the White Sox, 2022 might be the most Reinsdorfian. Sure, one could point to the White Flag trade of 1997 to show his disregard for what happened on the field. You could point to his hardline stance on the lockout of 1994, where he valued breaking the union far more than having a World Series contender. Or you could go back to him threatening to skip town for Florida, using a beloved local institution as leverage to earn more money.

But this is the year where all of Jerry’s worst tendencies really came to bear. This is the year where institutional rot, a culture where the vague idea of loyalty euphemisms sycophancy and the best way to stay in good graces is to ask no questions, threatened to slam shut a window of contention and turned a thing of beauty into a misery.

Let’s review?

  • Showed what loyalty meant by forcing Lucas Giolitio, a standout pitcher and human being, into arbitration. A handful of nickels was prized over actual loyalty, decency, or long-term reputational thinking.
  • Free agents that the Sox rejected, most notably Bryce Harper, led their team to the playoffs. Harper especially stings — Reinsdorf feels it is more important to avoid Scott Boras than to sign the best players.
  • The money that wasn’t spent on Harper (or Manny Machado, Zack Wheeler, etc.) was spent on a collection of relievers and replacements who were more or less no help.
  • We went into Year 2 of the Tony La Russa Apology Tour, where Reinsdorf forced a washed-up drunk onto a team of young, exciting players in order to make up for La Russa’s firing 20-some years ago. Nothing — not injuries, underperformance, an allergy to launch angles — hurt this team logistically and morally more than TLR.

There are a couple of interesting, extremely Reinsdorfian things here. It’s not that Jerry won’t spend; the Sox had a Top 10 payroll this year. It’s that he won’t give out huge contracts. He would prefer to spend $35 million on has-beens and never-will-bes, on washups and mediocrities, than spend $30 million on a star who happens to fill our biggest holes.

Why? Because he knows he’ll make money regardless. And it is more important not to give out big contracts, because then the unions and the players have even more power. Reinsdorf values money, of course, but he more values the principle of power. He could make more money by signing great players and winning, but at what cost? It’s a principled stand, of sorts, but the rich are always willing to sacrifice negligible amounts of money to protect their class.

The TLR fiasco is another classic Reinsdorf inversion. Hey, he cares about his friend! He feels bad over a decades-long slight. Now, in reality, his White Sox firing ruined Tony’s life to the tune of becoming a millionaire Hall-of-Famer, but still. In 2020, the Sox had a great team. Jerry figured that his old buddy could easily win a World Series, and he wanted to do him a solid. So here — take the team.

That’s not loyalty in any real sense. It’s not loyalty to the people who care about you, who have no power. It’s not loyalty to the fans, to the organization, or to the city. It’s loyalty to the idea that there are two groups of people: Me and my friends, who matter — and everyone else, who should just listen.

This ethos is exactly how Reinsdorf runs the Sox. Surround yourself with people who depend on you for employment, and who will never push back. Do enough to make money, but not enough to really have to spend it. Keep the long-term in mind — not on the field, but for the league and the business of the White Sox. Protect the ownership as a class. Protect their prerogatives. Embrace the rich. The product is important, but not too important.

It’s true that there are more important things in life than winning, but when it comes to how Reisndorf does business, none of them are particularly good or noble. He pulls up the ramparts and closes the gates and calls it home. He wants us to be grateful he lets us in to watch. He expects gratitude from everyone for his ability to make money.

I’ve seen it argued that he’s the worst owner in sports, a fluke 2005 and lucking into Jordan being his saving grace. I don’t know about that — while there is institutional rot, he isn’t gambling away proceeds, isn’t an obviously hideous racist, isn’t constantly involved in some kind of sex scandal. He isn’t a rich kid who has always gotten everything he wants. In short: He’s not Daniel Snyder, and for that we can take small graces.

But if he isn’t the worst owner in sports, Reinsdorf is perhaps the most owner-y. Being an owner, protecting what that means, making sure that other people pay the bills — that’s what drives him. Winning is incidental. This — owning the White Sox, bossing around the other owners, plotting for the future of the MLB — this is his job. It’s not a passion.

Reinsdorf is a working guy. He sees opportunities. He used a boring-ass court case to become rich, knowing how to defer taxes now to make a ton of money. That’s what he is still doing: Using the rules and the system to continue to make money, going to work every day, and seeing how he can succeed. That there are fans whose love is in the ledger is interesting, but incidental.

There is a hideous disconnect between the civic importance of a team and the pocketbooks of the people who run it. That is perhaps always to be the case. Failsons and tech tycoons and slumlords take over teams as vanity projects, and our happiness depends on them getting out of the way and not ego-fucking their way to disaster.

Reinsdorf was none of those things, but he is uninterested in bridging the divide. The team is part of his portfolio. He owns the Sox, and we don’t, and at the end of the day, that’s all that matters.

2022 White Sox Grades

Jerry Reinsdorf, OWN, -2.321
Jake Diekman, LHRP, -2.366
Rick Hahn, GM, -2.401
Bennett Sousa, LHRP, -2.425
Frank Menechino, BAT COACH, -2.469
Yasmani Grandal, C/DH, -2.549
Leury García, UTIL, -2.7
Adam Haseley, OF, -3.146
Joe McEwing, 3B Coach, -3.167
Ryan Burr, RHRP, -3.4
Tony La Russa, MGR, -3.5
Dallas Keuchel, LHSP, -3.9


He’ll outlive us all, but we still get to grade Jerry Reinsdorf. How’d we do?

This poll is closed

  • 8%
    Too hard, after all, he funded the No. 7 payroll in all of baseball.
    (20 votes)
  • 39%
    Too easy, just look at the guy he gave the spending money to.
    (97 votes)
  • 51%
    Wow, you know your stuff. Another appropriate grade.
    (126 votes)
243 votes total Vote Now

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