Chicago Skyway Privatization: How a $1.83B Deal Became a $3B Windfall for Foreign Investors

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TrailMarkers By Expedition Money

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Chicago Skyway Privatization: How a $1.83B Deal Became a $3B Windfall for Foreign Investors

TrailMarkers By Expedition Money

12 minutes 20 seconds

1 month ago

Chicago Skyway Privatization: How a $1.83B Deal Became a $3B Windfall for Foreign Investors

In 2005, Chicago Mayor Richard M. Daley faced a $220 million budget crisis and made a bold move: privatize the Chicago Skyway, the city’s 7.8-mile toll road. Sold for $1.83 billion, it promised immediate relief—but decades later, the city is still paying the price.

This episode dives deep into the full story of the Chicago Skyway privatization:

-How Chicago sold a perpetual money machine while foreign investors pocketed billions.

-The bidding war that stunned city officials, leading to CRA and McQuary’s record-breaking purchase.

-How toll hikes and long-term contracts ensure 82 more years of private profit.

-The financial reality for Chicago: short-term gains vs. long-term losses for taxpayers.

-Lessons on infrastructure privatization, short-term political wins, and the risks cities face when selling public assets.

Discover the shocking truth about one of America’s first privatized highways and why Chicago drivers continue paying the toll—literally and figuratively—for decades to come.

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