Chicago’s 2008 lease of its 36,000 parking meters for $1.16 billion was meant to solve budget woes without raising taxes. Investors, led by Morgan Stanley, calculated the deal using present value models, prioritizing immediate returns. The city council approved it quickly, despite warnings from Alderman Scott Waguespack about long-term costs. Soon after, parking rates soared, meters malfunctioned, and the public grew angry as they paid more for less. Hidden documents revealed flawed projections that underestimated future revenue, funneling profits to private operators early in the 75-year term. The city even had to pay penalties when removing meters, losing control over its own infrastructure. What looked like a financial lifeline became a symbol of shortsighted governance and the risks of privatizing essential urban services.