Chicago woman says it’s “crazy” the city won't take responsibility for a 300 lb. pole that fell on her car. Why suing City Hall is so hard

"It's kind of crazy the city isn't taking responsibility for it," Puetz told CBS News.

Or other such cases. From 2021 and early 2026, falling light poles resulted in 64 damage claims totally $1.2 million, CBS News discovered. The city only paid out two claims — for a total $9,300. Six claims are still pending. The rest were denied.

This reveals how tough it is to win a claim against a municipality, and why you'll likely have to go to great lengths if you want to fight City Hall and win.

How cities avoid potential lawsuits

Puetz's claim was denied, the city reportedly told her, because no one had alerted them of the rusty light pole and its need for repair.

That's in line with what legal experts note as one of the main hurdles in suing a city over personal injury or property damage: proving that the incident resulted from the city's neglect (2).

A case from earlier this year in Wildwood, New Jersey, resulted in a similar outcome (3). The plaintiff's foot became caught in a water meter pit that had a loose cover, causing her to trip and suffer multiple injuries to her left shoulder and foot, requiring surgery.

The court, however, found that the city couldn't be deemed negligent because they had not been notified of any safety issue with the cover of the water meter pit (4).

In addition to proving negligence, many city governments enjoy what's known as "sovereign immunity" — essentially making it illegal to sue them unless under specific conditions that can vary from state to state.

For example, in Chicago, a local law firm noted that proving simple negligence isn't enough to sue the city (5). They explained that you'd have to prove "willful and wanton misconduct" that caused harm or exhibited a "conscious disregard" for public safety.

An example, they added, is an instance of police brutality, illustrating the high bar for lawsuits against some municipalities.

And for those who do manage to file a successful lawsuit, the amount in damages that you can receive are often subject to caps imposed on a state-by-state basis (6).

That said, sometimes justice does prevail. In Charlotte, North Carolina, in 2022, an elderly woman suffered a raw sewage backup into her home, for which she requested $65,000 to cover the damages (7).

The city rejected her request and offered her $45,000 if she released them of liability, which she signed. An appeals court, however, ruled this month that the deal "was obtained through undue influence" by the city, as the woman felt pressured because she might otherwise lose her home. The woman is now cleared to sue the city to cover the damages.

How to sue City Hall and win

Legal experts warn that, for those looking to sue their municipality for damages or personal injury, the clock is already ticking.