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For all his mishegas and misdirection, Chicago White Sox chairman Jerry Reinsdorf is right on one thing: It’s either now or later.

Either he’s asking the city and state for more than a billion bucks of public money for a new stadium right now or someone else is going to be asking for it down the road.

The prospects of the White Sox leaving town have been rumored for months, from the rumors of a Nashville interest to Reinsdorf’s more direct insinuation in a recent interview with Crain’s Chicago that someone will buy the team and want to move it.

With his 88th birthday coming up, Reinsdorf’s focus right now isn’t on the team’s improved defensive outlook or the Bulls’ march to the Play-In Tournament. He’s all about a new stadium.

This rare media interview with Crain’s immediately followed his trip to Springfield, Ill., to schmooze with state legislators in his quest for a new stadium that would be funded by someone other than him.

Few people outside of Reinsdorf’s immediate orbit are enthused about the idea of funding another ballpark for him. But in Reinsdorf’s world, Chicagoans are all downwind of his cigar smoke, forever looking for a breath of fresh air.

These days, it’s offensive to our more educated sensibilities when sports franchise owners ask for public money. It’s wildly offensive when it’s coming from Reinsdorf, a rich owner of two teams with his hand out for the second time.

It’s not surprising that Jerry is seeking “free” money, of course. He’s an owner. It’s what they do.

Reinsdorf still has his defenders who are loyal to him, but even they can’t argue that the White Sox are not a perennial disappointment under his leadership. Sure, you can shift the blame to the front office or the players or even the fans, but you can’t argue the facts. Jerry is the boss and his business is bad.

Just a few years ago, the Sox were the darlings of the city, a 93-win team with strong personalities and a bright future. Now, after a series of calamities, they’re entrenched again in the AL Central bunker — the big-city losers in a small-market division.

And Reinsdorf is back to his late-’80s tricks, trying to convince everyone that a new ballpark will not only be some kind of competitive panacea for his club but also a boon to Chicago and the state of Illinois. And if he doesn’t get what he wants, well, the team might not be playing in Chicago in the near future. He’s just trying to help.

Back in the day, he used Tampa-St. Petersburg to get his new park in Chicago. Nowadays, he’s not going to realistically threaten to move the team himself. In that interview with Crain’s, he’s threatening that the prospective owners who will one day buy the Sox, likely after his passing, will probably threaten to move the team. So just give him the money now to prevent that from happening.

I’m here to say that in that regard, he’s not wrong.

Whoever buys the Sox, whether it’s in a few years or a decade from now, will probably want a new stadium if the team is still playing at Guaranteed Rate Field. Now, there are some potential owners who might see the value in keeping the Sox where they are and doing the things to fix up the park and the surrounding area that Reinsdorf is unwilling to do. But I can see it playing out like it did when Tom Ricketts and his family bought the Cubs. Ricketts waited until after his first season as the owner to unveil a plan that would have taken control of existing tax dollars to fund money-making improvements for his private business.

Ricketts was unsuccessful at getting hundreds of millions of dollars (though he did get some help) to renovate Wrigley Field and its campus. But he got it done just in time for the Cubs to finally win a World Series.

The reason the Cubs didn’t move to Rosemont or anywhere else is because Wrigley Field is a cash cow. Guaranteed Rate Field is not.

The White Sox have a smaller fan base than the Cubs, and their stadium is not a tourist attraction. So the owners could threaten to move. But that’s in the future. Right now, the state and city have more pressing issues, financial or otherwise. Gov. J.B. Pritzker has said he’s not looking to give money to team owners for new stadiums. Chicago mayor Brandon Johnson, who ran as a progressive, is under pressure from two teams now looking to move.

From a public relations standpoint, unknown owners would get more support for asking for tax dollars than Reinsdorf. For all the philanthropic work the Sox have done in the community, for all the loyalty he’s shown to his employees and for all the genuine love he has for baseball, Reinsdorf has squandered all the goodwill he’s ever had.

Reinsdorf has said for years he wants his sons to sell the team when he passes. The partners in his ownership group, some of whom have been with him since he bought the team in 1981, will demand it. But the Reinsdorf family will make out very well when it happens.

In 2021, Michael and Jonathan Reinsdorf offered to buy ownership stakes from the team’s limited partners, albeit at a low valuation. Some partners did take them up on it, which has added to the family’s stake in the franchise. Jerry Reinsdorf told Crain’s he owns more than the 19 percent of the team that Forbes has reported.

An agreed-upon deal for public money for a new stadium will add significant value to the franchise, which is already estimated to be worth around $2 billion. So it makes sense he’s trying to square that away now. Think of this as estate planning.

If the White Sox’s days in Bridgeport are numbered, it’s a shame. For all the whining you hear about it, it’s actually a pretty good South Side location, just off the highway and near a Red Line stop.

The stadium is facing the wrong way and the area surrounding it has the ambience of the Woodfield Mall parking lot, but the Armour Square neighborhood has been the home of the team since 1910, so there’s some history there. The Sox never did enough to create a “ballpark village” type of environment, nor did they market the stadium and surrounding neighborhood well enough to convince tourists to check it out.

If the team were good, year after year, attendance would reflect it. But don’t tell Reinsdorf that. He’s in excuse mode. It’s a PR strategy and a way of life.

In one of the more galling parts of his Crain’s interview, Reinsdorf told Crain’s reporter Greg Hinz that the team’s attendance issues were solely because of the ballpark’s location and not the result of his decades of poor decision-making.

Reinsdorf says Sox need a new stadium to compete — and stay in Chicago https://t.co/TUgWGJGGU6

— Crain’s Chicago Business (@CrainsChicago) February 21, 2024

Reinsdorf pointed out that after the team’s World Series victory in 2005, “we didn’t crack the 3 million (attendance) mark” in 2006.

In that season, the Sox “only” drew 2.96 million, which remains the franchise’s high mark and proves the opposite of his point. That showed what happens when the Sox’s success pushes people to buy season tickets. It was an increase of more than a million fans from 2004, the year before the World Series.

After the ballpark opened to big crowds, attendance cratered in the mid-1990s after the strike canceled the Sox’s chance to win a World Series. Reinsdorf was a labor hawk and a public villain in that fiasco.

After the Sox won the World Series a decade later, the team couldn’t build on that momentum and attendance then declined for eight consecutive seasons, going as low as 1.65 million in 2014.

In that span, the team had five losing seasons and made the playoffs just once. After winning the division in thrilling fashion in 2008, the Sox embarked on an 11-year run of missing the postseason.

The team drew 2 million again in 2022, the year after it won its division. In that 2021 season, ballpark attendance was curtailed by pandemic regulations. But after they were lifted, the Sox were drawing weekend crowds of more than 30,000 fans a game. The Cubs were down and the Sox were up.

Last year, the Sox had the largest attendance decrease in baseball (minus-339,731, according to Baseball-Reference) and it wasn’t because it’s a schlep to get to Bridgeport. Basically, all of baseball saw an attendance increase or stayed relatively flat except the Nationals and White Sox. Washington was down 1,982 fans per game and the Sox lost 4,194. The fans have turned against this team and these attendance patterns show, again, if you win, the fans will come to the South Side. And if you don’t, they won’t.

Sox fans are tired of being disappointed, and after a 101-loss season, it’ll be a struggle for the Sox to draw 1.6 million in 2024. Also, the team’s well-liked TV broadcaster Jason Benetti left for a job with the Detroit Tigers.

Meanwhile, the Tampa Bay Rays, who are still trying to escape the dome built for Reinsdorf’s team and draw like a minor-league team, make the playoffs nearly every year against the stiff competition of the AL East. Of course, they are a progressive, savvy organization that has figured out how to win consistently on a shoestring budget. Reinsdorf, meanwhile, waxes poetic about how much he loved David Eckstein because he tried hard.

A South Loop ballpark in the midst of a newly developed neighborhood along the river is certainly intriguing. The renderings look fantastic, as renderings always do. The idea of a new stadium, a restart, sounds great, but is it worth well over a billion dollars in tax money?

A rendering of a potential new ballpark for the White Sox in the South Loop. (Courtesy of Related Midwest)

The Cubs are the only team in town that brings in a significant amount of new money to the city because of Wrigley Field. People will visit Chicago to go to Cubs games and then spend money around the city. Now it’s not as much money as the team’s research would have you believe, but it’s not nothing.

The Sox have a smaller fan base than the Cubs and they don’t have the benefit of being in a bustling North Side neighborhood and a tourist attraction of a ballpark. With local support, they’re a team that should be drawing around 2 million to 2.5 million a year. But they need to win.

Reinsdorf had enough of the failed rebuild (and its high payrolls) last season, firing his most trusted executive, Kenny Williams, and general manager Rick Hahn. In rare public comments, Reinsdorf said he was in a hurry to get better so he promoted the team’s farm director, Chris Getz, to GM. Getz is rebuilding the team on the cheap, focusing on sure-handed defenders and clubhouse guys. Projected 2024 win totals vary, from 65.6 (PECOTA) to 67 (FanGraphs).

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With the team’s baseball present looking grim, why not look to the future?

With the Bears also fishing for help for a new stadium, either in the city or on their land in Arlington Heights, Reinsdorf is trying to be proactive for his own slice of the pie.

The financing structures for a new park, as discussed by Reinsdorf and the developers Related Midwest, involve an existing city hotel tax and possibly taking on and extending the debt for the Sox’s current park and for Soldier Field over the next few decades or so. They also want a special taxing district and to use the money the city has already pledged to help with infrastructure improvements in the area. They want a lot and they’re promising a lot.

But of course, these kinds of stadium plans always rely on rosy tax projections and promises that don’t often come true. But it won’t be Jerry’s problem.

It’s been 33 years since New Comiskey Park opened after the governor and state leaders stopped the clock (literally) to help Reinsdorf.

Where will this franchise be in another 33 years?

Reinsdorf will be long gone. The politicians will have moved on. The White Sox could be playing in the South Loop or Nashville or Portland.

Maybe by then, the team will have finally signed a free agent to a $100 million contract. Maybe by then, the White Sox, and their fans, will be happy with their lot in life and in baseball. Maybe the Sox will have added another World Series trophy to their case.

The word “maybe” allows for all kinds of possibilities without any guarantees. Kind of like when an owner tells you how perfect a new stadium will be for everyone.

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(Top rendering: Courtesy of Related Midwest)