Jerry Reinsdorf cares about winning, not money, says Jerry Reinsdorf

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Jerry Reinsdorf purchased the White Sox in 1981. From 1981 through 2022, the White Sox have posted a record of 3,313 wins and 3,262 losses, for a win percentage of .504. They’ve made the postseason just seven times in that stretch, and in all but one of those appearances, they lost in the first round, whether said first round was an ALCS, ALDS, or Wild Card round. In 2005, they won the World Series, the franchise’s first even appearance in the Fall Classic since 1959, and the organization’s first championship since 1917 — two years before the Black Sox betting scandal.

Payroll data isn’t widely available or consistent past a certain point, but we can pretty easily look back to at least 2000 thanks to Cot’s Contracts, and get a look at where Reinsdorf’s White Sox tend to rank in that arena in the aftermath of two waves of expansion as well as the 1994 strike and its fallout, which eventually included a luxury tax and revenue-sharing. The number in parentheses is the team’s rank in a given measurement:

The average rank of their Opening Day payroll, from 2000 through 2023, is 15th — 14.79, if you want to give them a little extra credit (but you shouldn’t). That’s right in the middle, since the current 30 teams have all existed since that data. On occasion, Reinsdorf opens up his wallet and spends, as evidenced by the trio of fifth-ranked seasons following the 2005 championship as well as jumping to seventh in 2022, but it’s also worth pointing out that the last of those three seasons occurred 15 years ago. Of note as well is that the White Sox have never exceeded the luxury tax threshold. I would just like to point out that even the Marlins have paid a version of the luxury tax penalty before.

Why lead with all of this information? To make sure this recent quote from Reinsdorf hits just right:

“My approach has been I never really cared about making any money, I just want to win. Now, that’s not what I wanted to do in business. … The first week I was in sports somebody said to me ‘If you listen to the fans, you’ll soon be sitting with the fans.'”

Reinsdorf, at least in baseball, has very little winning to point to. He has a whole lot of caring very much about money you can look at, but you can say whatever you want when you’re at a business convention as an invited speaker and are worth over a billion dollars, as Reinsdorf was. You should feel free to say that whatever winning culture Reinsdorf’s Chicago Bulls team once possessed left with Michael Jordan, as well, since they were constantly winning titles or at least in the mix back in the 80s and 90s with one of the most successful athletes ever around, and since then? Well, the Bulls have had some pretty good seasons in the past couple of decades, sure, but they’ve also been mediocre much of the time, and have a White Sox-esque run of first-round series losses behind them now, as well.

One of the things that’s funny about Reinsdorf saying he cares about winning and not so much money is that I don’t have to do any kind of deep dive to say he’s full of shit. The above is just some pretty easily referenced material that’s around. Other things I could say include statements like, “Jerry Reinsdorf and Bud Selig were the best of friends, and both involved in the collusion of the 1980s as well as the settled before an arbitrator could make a decision on it collusion of the early aughts.” Or I could just copy and paste this paragraph from his Wikipedia page, with its embarrassing number of cited sources that prove Reinsdorf is a militant anti-union hardliner who was a significant source of the push behind salary caps and limits on draft spending. Which I will do, because we all deserve a little break some time:

As a basketball owner, he has been described by Time as a “cheapskate”,[33] a reference they also use for his baseball persona.[34] As of 1995, the time when Scottie Pippen was eager to either be traded or be rid of Krause, he had never renegotiated a contract.[32] As a baseball owner, he has had a reputation as one of the most militant, anti-union, hard-line owners.[12][35][36] Newsweek described him as “one of the hardest heads in the 1994 baseball strike“.[32] In the baseball offseason between the 1992 and 1993 seasons, he completely abstained from the free agent market.[37] Reinsdorf was one of the last holdouts to the 1996 labor agreement that instituted the salary cap while retaining arbitration rights for the players.[38][39] His 1996 signing of Albert Belle made news because of his widely publicized general opposition to spiraling player salaries.[12] The $55 million signing was a turning point in the decision by the baseball owners to agree to revenue sharing.[40] The signing also made Reinsdorf the employer of the highest paid Major League Baseball player and highest paid professional basketball player (Jordan) at the same time.[12] Reinsdorf had just re-signed Jordan after the 1995–96 NBA season.[41] However, Jordan had been underpaid most of his career,[42] and Reinsdorf, who did not feel he could justify the $30 million salary from a business standpoint,[43] immediately realized he was going to soon feel buyer’s remorse.[44] Even his most successful baseball team was not highly paid: when the White Sox won the 2005 World Series, Reinsdorf had the 13th highest payroll of the 30 Major League Baseball teams.[34]

Look at all of that blue text and those citations! You could go down a real rabbit hole of “Jerry Reinsdorf loves money much more than he loves winning” that covers the last 40-plus years, if you wanted to. Or you could just accept that Reinsdorf either believes his own lies, or assumes you’ll believe them, and doesn’t really care if you don’t. He’s going to spread them, regardless, and if his teams happen to win again before he’s no longer the owner, he’ll take full credit for that like he’s still taking credit for successes that are decades behind both organizations as if those matter in the present.