The City that Sold its Streets
In the waning weeks of 2008, the air in Chicago was sharp with more than just winter. The financial crisis had torn through the country like a bitter wind, and the city, like so many households it served, was scrambling. Unemployment in Illinois was climbing toward 8%, commercial tax revenues were drying up, and the housing market had seized. The global economy was in free fall—and city budgets, which rely on real estate taxes, sales tax, and business activity, were hemorrhaging.
The city faced a $500 million budget shortfall going into 2009. Mayor Richard M. Daley, in office since 1989, had long championed the idea of modernizing city assets and infrastructure through public-private partnerships. But with Washington slow to deliver federal relief and the state government drowning in its own fiscal crisis, Daley needed money—and fast.
That’s when Wall Street came calling.
Morgan Stanley led a consortium of investors under the name Chicago Parking Meters, LLC. Their proposal? A lump sum of $1.15 billion in exchange for the rights to operate—and profit from—the city’s parking meters for the next 75 years. On paper, the offer looked generous. It was a quick fix. A cash injection that could plug the gap, stabilize operations, and prevent tax hikes or service cuts in the short term.
There was little time—or appetite—for deeper scrutiny. In a whirlwind 48 hours, the deal passed through City Council with only limited debate. Just five aldermen voted against it.
The ink was barely dry when the cracks began to show.
The very next year, Chicagoans returning to the Loop after the holidays found meter rates had more than doubled. In some neighborhoods, meters that had cost 25 cents an hour were now $1.00. In prime areas, the rate jumped to $6.50 an hour. And the new operators enforced the rules with ruthless efficiency—issuing tickets, extending hours, even charging for parking on Sundays.
The real shock came when people realized just how much control the city had handed over. If Chicago wanted to shut down a block of meters for a street fair, parade, or roadwork, it now had to compensate the private company for lost revenue. The city had gone from owner to tenant of its own streets—and the rent was steep.
Then came the financial autopsy. The city’s own inspector general concluded that the meters had been grossly undervalued. The investors were projected to recoup their entire $1.15 billion in just 20 years, leaving over five decades of revenue still ahead of them. The total profit? Estimated at over $9 billion.
Chicago had sold a 75-year income stream for the equivalent of a payday loan. The budget was balanced for a moment—but at a staggering long-term cost.
In the years that followed, as frustration mounted, so did the finger-pointing. Some blamed Wall Street for exploiting a desperate city. Others blamed City Hall for its haste. And others saw it as emblematic of the broader collapse unfolding in 2008: institutions grasping for liquidity, reacting rather than planning, mortgaging the future to survive the present.
But perhaps most tragically, no one could undo it. The contract was airtight. The meters would belong to the consortium until the year 2083.
If this sounds like something that could never happen in your own financial life, think again.
Because Chicago didn’t make this deal out of greed. It did it out of fear. The city was facing a once-in-a-generation crisis, and like many people in financial distress, it reached for the most immediate lifeline—without fully understanding what came attached to the rope.
This is the same logic that tempts people to borrow from retirement accounts to cover short-term bills, or refinance homes to unlock equity they’re not ready to lose, or accept complex financial products that promise relief but deliver regret. It’s not that these options are inherently bad. But they are rarely free.
And they almost always come with a cost that is hardest to calculate in the moment: flexibility.
Once the city signed that lease, it could no longer adjust meter rates or policy without paying someone else. It had given up control over a crucial tool of local governance. In the same way, when individuals give up liquidity or lock in decisions that can’t be undone, they’re often limiting their future options without realizing it.
Financial stress has a way of narrowing our focus to the next month, the next bill, the next quarter. But the decisions made under duress often outlast the crisis itself. The key is not to avoid hard choices—it’s to make sure they’re built on a foundation of understanding, not desperation.
Because, like Chicago, we all have streets. Assets. Tools. Rights. Things that serve us daily, often unnoticed—until we lose control of them.
Chicago’s story is not just about meters or mayors. It’s about what happens when fear overrides foresight, when urgency eclipses understanding, and when we treat temporary relief as a permanent solution.
Don’t sell your streets.