Exasperated by the cost, Chester began to look for flaws in the system that he could exploit. He noticed that enforcement was spotty around where he worked, and as a self-described “politics and urban transit nerd,” he knew enough details of the meter deal to have a cursory understanding of how the money flows.

While the group that owns the lease collects all the money from meter payments, the revenue generated by ticketing goes to the city. Chester speculated that if he stopped feeding the meters entirely and paid his tickets on time, not only would all the money he spent go to the city, but he would actually end up paying less overall.

“We all gamble with it a little around the city, right?” Chester tells me when we meet up. “And I started gambling with it, because it was just like, Man, I can’t pay this every single day. Eventually I did the math, and I was like, Screw this.”

This was approximately two years ago. Whole weeks would go by without Chester getting a single ticket. When a parking enforcement agent would slap an orange envelope on his car, he would make sure to pay up on time. At one point, he thought the enforcement folks had gotten wise to him. Two days in a row, he found a ticket on his windshield. “All the tickets only came in the morning, at 9 a.m., and so I started paying the meter for the first hour and then I didn’t pay for the rest of the day.” Eventually he stopped entirely, and things went back to normal, which meant an average of slightly less than two tickets a month.