In practice, that depends on the contract. I bet Uber had more, higher-paid lawyers than the town.
Clearly you have never faced the wrath of a small town town-council member who has the ability to ratify by-laws and knows everyone in town by their first name!
I pity the high-priced lawyer who thinks he can battle small towns. It'd be easier to battle a big city regulator any day.
The company being hired is famous for dodging regulation.
You can only dodge so long, and eventually you take one to the chest.