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Chicago's Bold Move: Selling Unpaid Debt to Investors

Chicago, Illinois, USAFriday, February 13, 2026
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Chicago's Unprecedented Move

Chicago is making a significant move. The city plans to sell approximately $1 billion in debt. This debt stems from sources like unpaid parking tickets. The city hopes investors will be interested in purchasing this debt. However, there's a catch: a top finance official has warned that this venture is risky and could be costly.

A First for the Third Largest US City

This is a first for Chicago, the third largest city in the US. The city has never attempted this before, not on this scale. Michael Belsky, Chicago's comptroller, informed council members of this plan in a letter last week. Despite the risks, Chicago is proceeding with the plan.

Why is Chicago Doing This?

The city has a significant amount of unpaid debt and is in need of funds. Selling this debt could provide a solution. However, there's no guarantee. Investors might not be interested, or they might demand a high price, making the deal expensive for Chicago.

An Unusual Experiment

Selling debt in this manner is unusual. It's a big experiment, and the outcome is uncertain. Will it work? No one knows for sure. But Chicago is willing to try. The city hopes to turn a problem into an opportunity.

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