Parts One and Two

Jerry Reinsdorf knows exactly how to win. The question has always been when he wants to.

A tax lawyer bought the White Sox for about $20 million in 1981. Forty-five years later the worst team in modern baseball is in the playoffs, the owner-in-waiting wants 80 acres of riverfront, and the public still owns the old ballpark. Part One is the man. Part Two is the land.

Chicago · 30 September 2026

This is how it ends.

Sometime early in the next decade the @whitesox open a new brick ballpark on the Chicago River, south of Roosevelt Road, on land where Amtrak used to service its trains. Justin Ishbia runs the team. Amtrak’s trains get serviced in Bridgeport now, a long fly ball from the old ballpark on 35th Street.

The old ballpark is still standing. It still belongs to the public. Nobody plays in it. Chicago hotel guests make the last payments on it in 2032.

Most of the pieces are already signed, funded or drawn up. What follows is how it got set up. Part One is the man who set it up. Part Two is the land.

On September 24 the White Sox beat Kansas City 9 to 1 and clinched a playoff spot. Two years ago this same franchise lost 121 games, more than any team in the modern history of the sport. It lost 101 the year before that and 102 the year after. It started this season 6 and 13.

The fans on 35th Street called it a miracle.

It is not a miracle. It is Jerry Reinsdorf deciding to win. He has done it before, more than once, and fast. That is what has driven Sox fans out of their minds for forty years. They know what the man can do. They have never been able to tell when he is going to want to.

The tax lawyer

Jerry Reinsdorf was born in Brooklyn in 1936 and got his law degree from Northwestern in 1960. His first job was as a lawyer for the Internal Revenue Service.

Before he ever owned a ballclub, Reinsdorf learned the tax code from the government’s side of the table. In 1964 he went into private practice building real estate tax shelters, the legal kind, where people with money put it into buildings and get a good piece of it back from the government.

In the 1970s he built a company called Balcor that raised money from investors for real estate deals. In 1982 he sold it to Shearson, the brokerage owned by American Express, for $102 million.

So when Reinsdorf walked into baseball he did not walk in as a fan who got rich. He walked in as a man who knew better than almost anybody how to hold something valuable, borrow against it, get the public to share the cost of it, and wait.

Two years

In January 1981 Reinsdorf and his law school friend Eddie Einhorn bought the White Sox from Bill Veeck for about $20 million. Reinsdorf put together a group of partners and ran it as the head of the controlling partnership. Forbes has put his own share at around 19 percent.

He has run the team for 45 years while owning less than a fifth of it. He never needed the whole pile. He needed control of the partnership.

Two years later, in 1983, the Sox won 99 games and the division. “Winning Ugly,” they called it. Two years from purchase to a division title. So much for the idea that a turnaround takes a decade.

The Bulls

In 1985 Reinsdorf bought control of the @chicagobulls for about $9.2 million. The team already had a rookie named Michael Jordan.

Between 1991 and 1998 the Bulls won six championships in eight years. In 1994 Reinsdorf and @NHLBlackhawks owner Bill Wirtz opened the @UnitedCenter with about $175 million of their own money. It is the only building in this story he helped pay for with his own money.

After the sixth title the team came apart. Jordan and Reinsdorf still tell that story two different ways, and we are not going to settle it here. What nobody argues about is this. When Reinsdorf decided to build a winner, he built one of the best teams in the history of American sports. When he decided it was over, it was over.

The midnight vote

By the late 1980s old Comiskey Park was falling down and Reinsdorf wanted a new one. He also wanted somebody else to pay for it.

So he found another city. St. Petersburg, Florida, wanted a team badly enough to build a dome with no team in it. The Sox were going to move.

On the night of June 30, 1988, the Illinois legislature raced a midnight deadline to pass a deal for a new ballpark. Governor Jim Thompson worked the floor himself. The bill passed. Reinsdorf said, “Now we stay.”

The public paid. The state created a public agency, the Illinois Sports Facilities Authority, to build and own the new park. It sold $150 million in bonds. The park opened in 1991 at a cost of $137 million. The bonds get paid with a 2 percent tax on every Chicago hotel room, plus $5 million a year from the state and $5 million a year from the city. If the hotel tax comes up short, the city covers the rest. That agency also carries the 2001 Soldier Field rebuild, and all of it is scheduled to be paid off in 2032.

The ballpark on 35th Street, the one now called Rate Field, belongs to the public. The Sox are tenants. Their lease runs out in 2029.

St. Petersburg opened its dome in 1990 and waited eight years for a team. The team it finally got, in 1998, was the Devil Rays.

In The Record we call this jumping the line. Move the asset, or threaten to, and let the cities bid. Reinsdorf ran it in 1988 and it worked. It comes back in Part Two.

Money is a tool

In the 1980s baseball’s owners quietly agreed not to bid on each other’s free agents. Arbitrators ruled it was collusion, and in 1990 the owners paid the players $280 million to settle. One example on the record is Reinsdorf’s. When the Yankees wanted Sox catcher Carlton Fisk, George Steinbrenner backed off after a phone call from Reinsdorf.

In the 1994 strike that canceled the World Series, Reinsdorf was one of the owners’ hardest liners against the players.

Two years later he signed Albert Belle for five years and $55 million, the richest contract in the game.

In July 1997, three and a half games out, he traded his closer and two starting pitchers for six minor leaguers. Sox fans called it the White Flag Trade and never forgave it. Two of those minor leaguers anchored the bullpen when the Sox won the division in 2000.

People call that a contradiction. It is one rule, followed every time. Hold the line when holding the line pays. Spend when spending pays. Quit when quitting pays.

2005

In 2005 the Sox won 99 games and went 11 and 1 in the playoffs to win the World Series, their first since 1917. Reinsdorf called it the most satisfying thing he ever did in baseball.

That makes six parades for the Bulls and one for the Sox. There are owners in this country who have held a team for fifty years and never seen one.

The long middle

After 2005 came a lot of years that were not that. Then the bottom fell out. The Sox lost 101 games in 2023, 121 in 2024 and 102 in 2025.

In the middle of it, in 2024, the Sox pitched a new ballpark on an empty stretch of the South Loop called The 78 and asked the state to help pay for it. That same year there were reports of Reinsdorf talking with a group that wanted a team in Nashville. The 1988 play, dusted off.

The state never took it up. The Sox lost 121.

By Forbes’ count this year the White Sox are worth about $1.94 billion. The team lost about $40 million on operations. About $20 million in 1981, about $1.94 billion now. A losing season does not change what that math says about the man who bought in.

When it pays

The players earned this. Colson Montgomery, Miguel Vargas and Munetaka Murakami each hit at least 30 home runs. Will Venable and Chris Getz built this team. The players did not read the lease, and the fans in the seats earned every minute.

But anybody who has watched Reinsdorf for 45 years knows the pattern. Purchase to division title in two years. Six Bulls titles in eight seasons. From 121 losses to the playoffs in two years. When he decides it is time to win, he wins fast.

The question was never whether he knew how. It was always when it paid.

Part Two is why it pays right now.

The clock

In June 2025 Reinsdorf, then 89, signed a deal with Justin Ishbia.

Ishbia is a Chicago private equity man. His firm is Shore Capital Partners. His family founded United Wholesale Mortgage, the biggest mortgage lender in the country, and he owns a big piece of it. He and his brother Mat own the Phoenix Suns. Forbes put Justin at $5.4 billion in 2024.

As announced, Ishbia puts cash into the team in 2025 and 2026 to pay down debt and keep it running. Nobody can sell control before 2029. From 2029 through 2033, Reinsdorf has the right to sell control to Ishbia whenever he chooses. After the 2034 season, Ishbia has the right to buy it.

Reinsdorf holds the clock. Ishbia’s money comes in now. Reinsdorf’s decision comes later, on his timing, inside a five-year window.

The timing is a tax lawyer’s kind of math. Under federal tax law, when somebody dies, whatever he owned gets valued fresh on the day he dies. His heirs can sell right after and owe little or no tax on everything it gained while he was alive. If the owner sells while he is still living, he pays tax on the whole gain since the day he bought. On Reinsdorf’s own share of a team bought at about $20 million and worth about $1.94 billion, that difference runs to nine figures. South Side Sox, a fan site that does its homework, put it at roughly $200 million back in 2022. That is their estimate, not a filing.

Reinsdorf is 90. Years ago he said the only reasons he would sell were health, family, or losing so much money it made no sense to keep the team.

The deal is built so the sale can happen after he is gone, on the best tax terms the law allows, with the buyer already locked in and the buyer’s money already paying the bills. No document says that. But it is the deal an IRS-trained tax shelter lawyer would draw up. He is holding an option, and the option is time.

The swap

Amtrak services its long-distance trains on about 47 acres along the Chicago River, running south from Roosevelt Road. Shore Capital, Ishbia’s firm, is under contract to buy it.

You cannot buy a working train yard unless the trains have somewhere else to go. So Amtrak is moving that work to the Canal Street Yard in Bridgeport, owned by the @UnionPacific railroad, with its main train shed between about 33rd and 35th streets. Right next to the old ballpark.

The new yard costs about $900 million. Three checks pay for it.

The federal government, $572 million, in a grant announced in August.

The federal government again, $87 million more for the rail bridges over the streets.

Ishbia’s development company, Canal Edge, the rest, including more than $125 million of his own money.

Federal taxpayers cover about three of every four dollars of the move. Ishbia covers the rest and ends up with 47 acres of riverfront a few minutes from the Loop, cleared of the one tenant nobody could ever move without somebody paying for it.

Ishbia is buying Amtrak’s old land partly by helping pay for Amtrak’s new land. In The Record we call it two registers, one office. The same man is paying in with one hand and taking out with the other, and the public is paying for most of what sits in between.

The letter Illinois’ members of Congress sent backing that grant mentioned “joint ventures.” Amtrak’s own public materials do not name Ishbia, do not say what happens to the old yard, and do not say whether the City of Chicago has to sign off. The environmental review has not been published.

Bridgeport got its community meeting after the money was already announced.

The ballpark nobody is asking you to pay for

On September 6 Ishbia unveiled the plan. He calls it The Railyards. With other purchases, including the old Union Station power plant, the site grows to about 80 acres. The drawings show a brick ballpark on the river, a plaza, towers of apartments, a small park and a Northwestern Medicine health center.

Ishbia says the ballpark itself will be privately paid for. That is the headline, and it is a change from 2024, when the Sox asked the state for help and got nowhere.

Canal Edge still wants public money for what surrounds the ballpark. The roads. The bridges. Maybe a new @Metra station. Help turning the whole site into what planners call a transit district. The total cost has not been disclosed past “the billions.”

The ask did not go away. It moved. In 2024 it was a stadium, and a stadium was a hard sell. In 2026 it is roads, bridges and a train stop, and a train stop is a much easier vote.

The ballpark left behind

The public still owns that ballpark. Its bonds, together with Soldier Field’s, still come out of the hotel tax and the city and state checks through 2032. The Sox lease ends in 2029.

On September 16, Block Club Chicago reported that the agency that owns the ballpark was blindsided by the plan to put Amtrak’s yard next door.

If the Sox leave soon after 2029, the public keeps paying off the old park for a few years with no team in it. And a rail yard that runs around the clock will sit next to it, which makes that land worth less to anybody who might want to build something there. The team takes the new park. The public keeps the old bill.

And the threat from 1988 is back, only smaller. Then it was St. Petersburg. In 2024 it was the Nashville reports. Now it is a move across the river. Same play, shorter trip.

Why the winning pays twice

That puts the season in a different light.

A 121-loss team is worth less at the closing table and is a hard sell at City Hall. A playoff team is worth more on both counts. More tickets, more TV money, more goodwill. A fan base that is back in love. A city that wants to keep the good times rolling. Aldermen who would rather be photographed at a playoff game than at a Bridgeport protest.

The winning pays once when the team changes hands, and again when somebody asks the public for roads and bridges and a train stop. The timing is Reinsdorf’s.

Where this lands

A tax lawyer holds the clock on the sale, 2029 to 2033. The buyer’s money is already paying down the team’s debt. The buyer is under contract for 47 acres of riverfront. Federal taxpayers are paying most of the cost of clearing it. The public ask has moved from the stadium to the ground around it. The old public ballpark has a lease that runs out three years before its last bond payment. And the worst team in modern baseball is in the playoffs.

Every one of those was a choice somebody made on purpose, by people who know what they are doing. It is smart, it is legal, and the neighborhood was never part of the math. That is how the game gets played by the men who own the board.

Bridgeport gets the rail yard and the hotel guests get the bill. For now, the fans get October.

Enjoy it. He is.

The scoreboard

Holes, named

Sources

The RulesThe RecordArchive