One of MLB's Worst Owners Announces He'll Step Aside...Maybe... In Ten Years

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Security personnel remove a sign depicting Chicago White Sox owner Jerry Reinsdorf that was hung from the upper deck during the ninth inning of a game between the Baltimore Orioles and Chicago White Sox at Guaranteed Rate Field on May 23, 2024 in Chicago, Illinois. Baltimore defeated Chicago 8-6. (Photo by Jamie Sabau/Getty Images)

Hi friends-

We *thought* we got a bit of good news yesterday when word leaked that Jerry Reinsdorf, the 89-year-old Lord of the Chicago White Sox, was selling the team to young private equity billionaire Justin Ishbia, who also owns the Phoenix Suns and the Phoenix Mercury along with his brother, Mat.

Ishbia had been in the running to buy the Minnesota Twins, but abandoned that plan back in February.

Now we know why.

The Ishbia news was initially met with unbridled joy from a battered fanbase that suffered through 121 losses last season and 101 in 2023.

Reinsdorf has owned the Sox since 1981 and the NBA’s Chicago Bulls since 1985. And while the Bulls achieved major success under his ownership (thanks to Michael Jordan), the Sox have come nowhere near accomplishing what they are capable of, given that they play in a large media market in one of the greatest cities on Earth. (Last year’s 121-loss season set a modern record in MLB futility).

In addition to being non-competitive in a winnable division, there has long been a sense around the game that the job of running a pro sports franchise has simply passed Reinsdorf by. (This is a man who somehow didn’t *like* Jason Benetti (?????), maybe the best play-by-play caller in the game, and ran him off to Detroit.)

As the second-longest tenured MLB owner behind the Steinbrenner Family (Yankees) he has long wielded considerable power over the sport, even if he’s now in his lion-in-winter era. There are good reasons to want him gone. He’s a hard line anti-labor hawk whose fingerprints were all over the 1994 strike. You can bet he will be a leading voice calling for a salary cap or a lockout at the end of next season, even if his overall influence is waning now that his good friend Bud Selig is no longer the league’s commissioner.

Reinsdorf’s lack of investment in player development and analytics has been embarrassing, as has his loyalty to guys like former GM Kenny Williams, who were not good at their jobs.

It’s not just that the White Sox have been embarrassingly behind other teams using modern technology to draft and develop talent: it’s also that Reinsdorf also been too cheap to spend on existing stars. The largest free agent contract he’s ever handed out to a baseball player was a five-year, $75 million deal he gave to…. Andrew Benintendi.

Reinsdorf has reportedly instructed his family to sell the White Sox when he dies, but keep the Bulls. So when news came out yesterday that Ishbia would take over ownership of the team, I did a little dance as I made my way through the Dodger Stadium press gate. As you all know, I believe the biggest problem facing MLB’s future is not player salary growth, but terrible owners. Reinsdorf is one. Dick Monfort in Colorado is another. John Fisher in Sacramento might be the worst, but Bob Nutting in Pittsburgh is putting up a strong fight for that title. Because I love this sport, I want all of these men to sell to people who who feel ashamed about putting a bad product on the field and treating their fans like garbage while lining their pockets.

As it turns out, my happy dance was premature. Maybe ten years premature, if Reinsdorf live to be 99. Maybe 20 years premature, if Reinsdorf lives to be 109 and Ishbia begs off.

Here’s the press release on this weird agreement from the White Sox:

CHICAGO — The Chicago White Sox today announced that Jerry Reinsdorf and Justin Ishbia have reached a long-term investment agreement that establishes a framework for Ishbia to obtain a future controlling interest in the White Sox. As part of the agreement, Ishbia will make capital infusions into the White Sox as a limited partner in 2025 and 2026 that will be used to pay down existing debt and support ongoing team operations.

The agreement provides that, from 2029–33, Reinsdorf will have the option to sell the controlling interest to Ishbia. After the 2034 season, Ishbia will have the option to acquire the controlling interest. In the event of any such future transaction, all limited partners of the Sox would have the opportunity to sell to Ishbia at that time. In addition to Justin Ishbia, his brother Mat Ishbia, and father Jeff Ishbia will also be significant investors. There is no assurance that any such future transaction will occur, and in no event will such a transaction take place before 2029.

Until such time, the Reinsdorf family will continue to own the controlling interest in the White Sox. Reinsdorf, chairman of the White Sox since purchasing the franchise in 1981, remains the sole day-to-day decision-maker for the club.

Let’s break this down as best we can. The Ishbia family is very rich. The White Sox appear to be carrying a lot of debt. Ishbia—who has held a minority stake in the Sox since 2021—has agreed to give the team more money this year and next year to help ease that debt. In exchange, Reinsdorf *might* sell a majority stake in the team to Ishbia between 2029-2033. If he does not do that, Ishbia will have the right to purchase control of the team after the 2034 season.

So basically, Reinsdorf will run the team through at least 2028—assuming he lives that long as he is 89 years old. And in theory, Reinsdorf *could* run the team through 2034, at which point he would be 98 years old.

Making things even more confusing: there’s no guarantee that Ishbia will even buy the White Sox. And If the Reinsdorf bloc of the Baseball Lords forces a lockout that costs us a year—or more!—of baseball and tanks the sport, Ishbia could simply walk away.

In a way, it’s as if Ishbia is loaning Reinsdorf money to remodel his mansion right now, and taking a commensurate stake in the property). And in return, he could exercise the option to buy that mansion in 10 years.

So a succession plan is in place. Sort of. Maybe Ishbia is the Kendall Roy of this mess and it will all end in tears. Maybe he is Tom Wambsgans, and it will all end in his lap. Maybe Reinsdorf will outlive us all.

In any event, we are stuck with him until further notice. Sorry, Chicago.

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AROUND THE LEAGUE:

• The Mets’ Francisco Lindor broke his right pinky toe sliding into second base at Dodger Stadium on Wednesday night. I’d cite an article about it, but I can cite myself since I was two feet from his face when he broke the news himself in the Mets clubhouse on Thursday. The switch hitter says he’s day-to-day, but that hitting right-handed may prove more of a challenge as he pushes off against that injured to from that side of the plate. He also said he doesn’t love the idea of pinch hitting, because if he’s well enough to hit he’d like to also be in the field.

• Luke Weaver also injured himself at Dodger Stadium this week, pulling a hamstring while warming up to close the game on Sunday. It seems as though Lindor and Weaver both contracted the flesh eating virus that has decimated the Dodgers pitching staff, and Chavez Ravine should probably be tented until further notice.

• The Braves blew a six-run ninth inning lead on Thursday and reacted by calling up Craig Kimbrel on Friday. I suppose there are some Braves fans who feel nostalgic about this, so for everyone’s sake I hope it isn’t a disaster.

• Diamondbacks ace Corbin Burnes is going to have Tommy John surgery. This is a brutal blow for the Diamondbacks, as Burnes is in the first of a six-year, $210 million contract. He will miss the rest of the season, and likely all of 2026 as well.

• The fact that Burnes blew out does not absolve Orioles GM Mike Elias and owner David Rubenstein for refusing to re-sign him or literally anyone good to replace him.

• The Birds are 4-0 to start the month of June and maaaaay be heating up, having won their last six. We shall see. Ripping off nine in a row with a sweep over the A’s this weekend would certainly help give them life.

• Former Cy Young winner Shane Bieber of the Guardians suffered a setback in his recovery from elbow surgery. Ugh.

• The Royals called up top slugging prospect Jac Caglianone this week. Cags is 1-for-13 at press time, because baseball is really hard. Nevertheless, we will root for dingers aplenty.

That’s all for this week! Paid subscribers are chatting baseball right now in the Substack app until the last pitch is thrown on the west coast tonight. Come join us!