Column: Jerry Reinsdorf’s clumsy handoff of the Chicago White Sox only adds to his checkered baseball legacy

If only Jerry Reinsdorf took the lead of former President Richard Nixon, who said goodbye to the media in 1962 after losing the California gubernatorial race.

“I leave you gentlemen now, and you will write it,” Nixon said. “You will interpret. That’s your right. But as I leave you I want you to know — just think how much you’re going to be missing. You won’t have Nixon to kick around anymore, because gentlemen, this is my last press conference.”

It wasn’t true, of course, for Nixon.

For Reinsdorf? Who knows?

Reinsdorf issued a statement Thursday revealing a “long-term” plan to sell the White Sox to limited partner Justin Ishbia. The statement confirmed a February report by The Athletic’s Jon Greenberg that said Ishbia, who had pulled out of a bid for the Minnesota Twins, did so in order to eventually take control of the Sox from Reinsdorf.

The report was greeted with the usual denials from the Sox, who said Reinsdorf would remain in charge until he decided otherwise, and Ishbia’s purchase of shares did “not provide a path to control” of the team.“ USA Today reported in April that Reinsdorf “has made it perfectly clear to friends that he has zero interest in selling as long as he remains in good health.”

For reasons unknown, Reinsdorf reversed course two months into another disastrous season and disclosed that path Thursday in clear language that could not have been more confusing.

And as it turns out, Sox fans will still be able to kick Reinsdorf around for four more years … or perhaps another nine years. Or maybe not at all.

It might be. It could be. But is it?

It all depends on whether he exercises his option to sell to Ishbia between 2029 and 2033 and whether Ishbia opts to buy in ’34 if Reinsdorf remains in control, assuming the billionaire still thinks it’s worthwhile to own a Major League Baseball team.

Justin Ishbia, right, and wife Kristen Ishbia sit courtside during a Bulls-Suns game on Feb. 22, 2025, at the United Center. (Erin Hooley/AP)

The Sox statement said there is “no assurance that any such future transaction will occur,” and certainly not until 2029 at least. That didn’t stop the countdown to the post-Reinsdorf era, which began Thursday with the Sox’s 3-2, 10-inning win over the Detroit Tigers at Sox Park.

Sure, we don’t know when we’re counting down to, but at least there is a “long-term investment agreement,” which should at least change the “Sell the team” chants to “Hurry up and exercise the sell option.”

The Sox rebuild theoretically should be done by the time the deal is done, although the possibility exists they will be on their third rebuild since 2016.

Without any real information, we only can speculate that the new dream stadium at The 78 will be Ishbia’s Great White Whale now. The Sox said he would be making “capital infusions” in 2025 and ’26 that will “pay down existing debt and support ongoing team operations.”

That probably doesn’t include the ongoing operation to solve the mystery of the gunshots in the bleachers in 2023. Ishbia isn’t a miracle worker, OK?

Efforts to contact general manager Chris Getz to find out whether these “capital infusions” will increase the team’s 29th-ranked payroll and give him a fighting chance to compete were fruitless. No response, though he could’ve changed his number. Getz told me before Monday’s game he would be talking with the media Friday, which gave him four days to rehearse.

Will Ishbia be the anti-Reinsdorf? It’s wishful thinking to believe Ishbia would pony up for free agent Kyle Tucker this winter if he can’t take real control until 2029. But it’s still legal to dream, or at least it was when this story went to print Thursday night.

I have plenty of unsolicited ideas for Ishbia that he can ignore, but I’ll keep it to myself for now and focus on Reinsdorf’s checkered baseball legacy, which is still in progress two months in his 45th season.

Fans watch as the White Sox and Tigers play on June 5, 2025, at Rate Field. (Brian Cassella/Chicago Tribune)
Fans watch as the Chicago White Sox and Detroit Tigers play Thursday, June 5, 2025, at Rate Field. (Brian Cassella/Chicago Tribune)

Barring a huge infusion of money to sign big-name free agents between this winter and 2029 or thereabouts, Reinsdorf will wind up with one title in nearly five decades, as well as a new stadium he didn’t pay for, no longer wants and only got after threatening to move the team to Florida. He was a leading hawk among owners — along with Tribune Co. — when they tried to implement a salary cap in 1994, which led to a players strike and his old pal, Bud Selig, canceling the end of the season with the Sox in first place.

He signed off on the “White Flag Trade” with the Sox 3½ games back in July 1997, approved the signing of misanthropic slugger Albert Belle and allowed former GM Rick Hahn to trade Fernando Tatis Jr. for James Shields.

Reinsdorf and co-owner Eddie Einhorn took the Sox off free TV before most of the city was wired for cable, and he also started his own TV network last year without a deal with the biggest cable provider, Comcast. Amazingly, that reportedly changed Thursday, and Sox fans soon can pay Comcast $20 more per month to watch them lose 100-plus games on the “Ultimate Tier,” which no doubt will be the “Ultimate Platinum Tier” in a few years.

Reinsdorf also has done some good things, such as hiring Ozzie Guillen as manager and later letting him roast Grifol as a Sox studio analyst. He gave us Steve Stone 2.0, signed Carlton Fisk and introduced the Campfire Milkshake. He kept head groundskeeper Roger “the Sodfather” Bossard around to make the field look great all these years and was a loyal boss to hundreds of team employees over the decades.

And during a 7½-hour rain delay of a postponed game against the Texas Rangers at old Comiskey Park in 1990, he offered free food and pop to the fans who stuck it out. He was a sports writer’s dream with his penchant for saying whatever popped into his head — until his advisers told him to clam up years ago.

But rest assured there will be no farewell party for the Chairman from Sox fans, either in ’29 or whenever it actually happens. The Sox remain one of only two teams, along with the A’s, that has never signed a player to a $100 million deal. Ishbia’s first task will be to fix the team’s hard-earned reputation as cheapskates and then to compete with the Cubs for Millennial and Gen Z fans who might want an alternative to the Ricketts machine.

Reinsdorf will be 98 by 2034, which is so far in the future we’re not sure there will be a future for him or for any of us.

It’s hard to fathom where we’ll be in nine years, just as it’s difficult to remember what we were doing nine years ago in 2016. That was the season that went south so badly it led to the trade of ace Chris Sale to the Boston Red Sox to start a rebuild that was supposed to make the Sox the team of the 2020s. It didn’t happen as planned, though the 2030s are suddenly looking a bit brighter.

Reinsdorf’s legacy also will be linked to his many GMs and managers, including Terry Bevington — the worst in Sox history — and current prospect whisperer Will Venable. Was it really five years ago that Reinsdorf hired his old pal, Tony La Russa, to take the Sox from Point B to Point C, then after one division title watched them go backward to Point A? It was definitely only last year that he let Grifol remain in the dugout despite evidence piling up right in front of his nose. Grifol declared “you either have to score more than them or have them score less,” yet Reinsdorf still waited until August to let Getz pull the trigger.

We’ll save our farewells until later, but for now we wish Ishbia all the luck in the world when he takes over the Sox in 20-something.

The clock is ticking.

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