A South Shore raid only highlights the city's disenfranchisement of its people.
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OCTOBER 21, 2025

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When I first saw the photos of the aftermath of the harrowing ICE invasion of a building in Chicago's South Shore, I knew there was a deeper story. Walls caving in, trash everywhere, gray laminate and subway tile still relatively new: it looked suspiciously like the wreckage of a real estate Ponzi scheme, and it was. As we explored earlier this year with the saga of Aurora, Colorado, the influx of Venezuelan migrants into American cities coincided with the bursting of a massive COVID-19 bubble in lower-end apartment buildings across the country, and often migrants are blamed for the sins of greedy financiers. What we found in South Shore was a long-running pattern of systematic financial looting (egged on for well over a decade by the Obama Foundation) that forces thousands of lower-income Chicagoans into sometimes hellish conditions.

–Maureen Tkacik, investigations editor

Kyle Mazza/NurPhoto via AP

The Lost Dream of Obam-a-Lago

A few weeks before the 2016 election, Chicago Tribune sportswriter Teddy Greenstein broke some tantalizing news: Tiger Woods was this close to signing a deal to design a luxury lakefront golf course right next to the site President Barack Obama had chosen for his new presidential library. The $30 million project would convert two existing public golf courses into one ritzier and more challenging PGA-caliber one, which would woo away bankers and Boeing executives from the suburban courses with the irresistible buzz of the Obama “brand,” which at the time boosters were counting on to revolutionize the presidential library genre into a full-blown Destination, a temple to the lame-duck president’s achievements, real and imagined. 


Nearly a decade later, the Tiger Woods golf course is almost certainly not happening, the Obama Presidential Center (the Obama Foundation decided to skip the library altogether and store the presidential archives in a suburban office park ten miles away, for some reason) is five years late, and the area on the South Shore of Lake Michigan is in the news again for having been the site of a traumatic ICE invasion, featuring a reported 300 federal agents descending upon a residential apartment building from Black Hawk helicopters and unmarked vans, smashing in windows, jimmying doors off the hinges, and zip-tying everyone in sight, immigration status be damned.


For the residents of Chicago’s South Shore, the ICE raids are not so much shock treatment as they are an uneasy new phase of a longer campaign of elite demolition of lower-class Chicago. The biggest scam in recent years, a $170 million “nonprofit” called the Better Housing Foundation, launched around the same time the Obama library was announced, and imploded two years later after 64 of its 81 buildings fell into such dire disrepair that the Chicago Housing Authority placed them on a blacklist for housing voucher recipients. Near simultaneously, a Florida-based enterprise called EquityBuild that had purchased nearly 200 buildings in the area sent thousands of investors an email advising them not to panic that their funds had been frozen, because “projects such as the Obama Library and the Jackson Park golf course … have helped drive values faster than we had predicted.”

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