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In this episode of Look Both Ways, David & Wes unpack the recent multi-billion-dollar resale of Chicago’s parking meter lease and why it matters. They explain the contract, including the compensation clause, and how it continues to hamstring Chicago’s ability to improve transportation. They also explore the less-discussed reality that some good has come from the deal such as a city that actually charges market rates for curbside parking. Then, borrowing a lesson from Taylor Swift, they explore how Chicago could someday afford to buy back their meters. Other topics: 🔹 Amtrak quiet cars… and maybe some party cars? 🔹 The future of useful transit 🔹 Trump’s love for mini-cars (he may be right) Stay tuned for biweekly conversations about all things transportation. Additional resources: Chicago parking meter deal: City's meters sold to another private company, Mayor Johnson says (https://abc7chicago.com/post/owns-chi...) Henry Grabar’s Paved Paradise: How Parking Explains the World (https://www.penguinrandomhouse.com/bo...) RTD’s CEO says charging for parking, focusing on events could help transit recover (https://denverite.com/2026/01/26/debr...) And David’s Mini-Car Stories... Tiny Cars, Big Opportunity (https://www.bloomberg.com/news/featur...) What Do US Vehicle Regulators Have Against Tiny Cars? (https://www.bloomberg.com/news/articl...) Music by Charlie Van Stee (courtesy of bensound) Email us at lookbothwayspod@gmail.com (mailto:lookbothwayspod@gmail.com) or find us at www.davidzipper.com and www.wesmarshall.org