The Record · Chapter Nine

Everything Must Go

The city ran short and started selling the things it owned. The roads, the curbs, and your share of the tax bill.

By Jason C. Wandel and Claude for Chicago Register · Monday, October 19, 2026

This is the stretch from 1992 to right now, October 2026, when the city ran short and started selling the things it owned. Last time the mills went dark, a bank got rescued, the workers’ checks bounced and the TIF pulled the growth downtown. Now look at what was left to sell. The roads, the curbs, the buildings, and your share of the tax bill.

Start with the road.

In 2005 Chicago leased the Chicago Skyway, the toll bridge to Indiana, to a group of foreign investors for 99 years. The price was about $1.83 billion.

Then the curb. In December 2008 the City Council approved a 75 year lease of every parking meter in the city for about $1.15 billion. The Council had a few days to read it. The buyers were an infrastructure fund group run by Morgan Stanley, holding half, and Deeside, owned by Allianz and the Abu Dhabi Investment Authority, holding the other half. The deal runs until February 2084.

Morgan Stanley is the same house as J.P. Morgan’s, just the grandson. The man who sat near the head of the table at the University Club in 1900 had a family firm holding your curb until last month.

The meter company borrowed $1.2 billion against those meters and paid its owners $353 million, according to its own 2019 audits. The city’s cut is supposed to be 5 percent. In 2019 and 2020 that came to nothing. In 2024 it was about $1.7 million.

On September 29, 2026, the City Council voted 46 to 3 to let a firm called Stonepeak buy the meter company. The price talked about at a June hearing was $2.53 billion, a number that doesn’t appear in the ordinance. Stonepeak is paying the city $75 million, earmarked for the pension funds. We covered that vote the day it happened, and what the aldermen got for their votes.

So the city sold the curb in 2008 for about $1.15 billion. In 2026 the same curb changed hands at $2.53 billion, and the city got $75 million out of it.

The ancestor of that deal is the Ninety Nine Year Act of 1865, which leased the city’s streets to the streetcar men for a century. Same move, better lawyers.

Now your tax bill.

When a big downtown tower appeals its property taxes and wins, it pays less. The city still needs the same total, so everybody else’s share goes up. The firms that won those appeals were run by the men who wrote the tax laws. Madigan and Getzendanner, the firm tied to the Speaker, cut about $1.46 billion off assessments between 2017 and 2021, more than any other firm. Klafter and Burke, the firm tied to Ed Burke, the city’s longest serving alderman, cut Trump Tower’s bills by more than $14 million over twelve years. The lawyers often kept up to a third of what they saved their clients.

Today the Board of Review’s commercial appeals shift about 3 to 4 percent of the tax base onto homes every year. That came to roughly $700 per Chicago homeowner in a single year.

The tower’s appeal is the bungalow’s bill. Write the rule, then sell the way around it.

Now the loans.

Between 2004 and 2012, Wells Fargo and Countrywide steered Black and Latino borrowers in Chicago into high cost loans at far higher rates than white borrowers with the same credit. Illinois sued both. Countrywide paid $335 million nationwide in 2011, and Wells Fargo paid $175 million in 2012. The banks that wouldn’t lend on those blocks in 1940 sold them the worst loans in the country in 2006. Buying a home is still the biggest check most families ever write.

Now the pensions. Chicago’s four city pension funds hold about $14.2 billion against about $50.6 billion they owe. That’s 28 percent funded, the worst of any big city in America. Every year that payment got skipped, somebody called the budget balanced. The bill went to people who weren’t old enough to vote yet. The sales tax is now 10.5 percent, the highest of any big city in the country. Two credit agencies downgraded the city in February 2026.

Book the benefit, skip the payment. The hole is the reason they give for every sale.

Now downtown, where the lenders are taking the keys.

In 2019 Lincoln Yards was promised up to $1.3 billion in TIF money and bonds. In 2025 the developer, Sterling Bay, handed about half the site to its lender, Bank OZK of Arkansas, by deed. In September 2026 the replacement project, Foundry Park, got $201.6 million in TIF from the Council’s Finance Committee.

In 2018 Brookfield paid $306 million for 175 West Jackson. In 2026 it sold for $41 million, about $29 a square foot. One South Wacker’s $343 million loan went into default in June. Downtown office vacancy sits around 27 percent.

And on October 7, 2026, Block 37, one of the 58 blocks on the 1830 map, the block the city knocked flat in 1989, sold for $30 million. The CTA had sunk close to half a billion dollars into a train station under it that never opened.

Thirty million dollars for a full block in the middle of the Loop, with everything it connects to running under it. Might as well call it a nickel.

When the bet fails, the lender owns the ground, and the public money already spent stays spent.

Now go back to the Calumet one more time.

The South Works land sat empty by the lake after 1992. In September 2025 a firm called Blue Owl bought parcels there for about $29 million and passed control to Related Midwest and CRG for about $58 million on a 99 year ground lease. The plan is a quantum computing campus. The county cut its tax assessment from 25 percent to 10 percent for thirty years. The public package is past $1 billion. A data center there could pull up to a gigawatt of power, and you know who picks up that check. Neighbors collected enough signatures for a referendum, and it was thrown out anyway. There’s no signed community benefits agreement.

Douglas pointed at the Calumet in 1852. Morgan’s men folded its mill into U.S. Steel in 1901. It went dark in 1992. Now it’s a 99 year lease with a thirty year tax break.

Same ground, same moves, run by different men.

Now the wins, because we print them.

In 2016, East Chicago finally ordered about 1,100 people, about 680 of them children, out of the West Calumet Housing Complex, built on top of an old lead works next to the smelter that ran until 1985. That came seven years after the EPA listed the site. It’s a win that came too late, and we print it that way.

The mayor declared $2.1 billion in TIF money surplus and sent it back to the schools, the city and the county. What held it was a pen in the right seat.

And on April 19, 2024, the federal government put 130 acres of the Shab-eh-nay reservation in DeKalb County back in trust for the Prairie Band Potawatomi Nation, 175 years after it was auctioned off while he was away visiting family. In March 2025 the state gave the Nation about 1,500 acres of Shabbona Lake State Park for one dollar. It’s the only tribal land in Illinois. The tribe’s chairman is Shab-eh-nay’s fourth great grandson.

What held that one was paper, and a family that never stopped asking for 175 years.

So here are our calls. We print them with dates so you can hold us to them.

One. Before the end of 2027, the city puts another public asset or stream of public money on the table for a long lease or a sale, and the pension hole is the reason it gives.

Two. Before the end of 2027, at least one more big Loop tower goes back to its lender or sells for less than half its last price.

Three. Before the end of 2028, the South Works campus gets more public money or a longer tax break before it hits the jobs numbers it promised.

If we’re wrong, we’ll print it right here with a date on it.

And here’s the question we’ve been asking since 1673. Whoever holds the crossing prices everything that has to cross it. So who holds yours?

The scoreboard

Read it yourself

Sources