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

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

Update: 2025-10-02
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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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    Chicago Skyway Privatization: How a $1.83B Deal Became a $3B Windfall for Foreign Investors

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

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