9. The Henry Hudson Bridge Accumulation $44 Million in Unpaid Tolls

Although cashless tolling has become the standard for many New York City, the system didn’t always work out too well. As the initial testing site of cashless tolling, the Henry Hudson Bridge became quite a costly venture for the MTA. According to a 2014 New York Post, one third of drivers failed to honor the cashless toll system. By 2015, drivers had avoided $4 million in toll bills that were mailed to them.

The uncollected toll money also resulted in the accumulation of an additional $40 million in late fees and violation charges. Yet, despite this daunting figure, the MTA still considered the program a success, making the cashless tolling option a permanent fixture on the bridge in January 2015.