The parking war centers on several private lots, whose owners argue drivers routinely park there while frequenting other businesses.
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Those owners posted signs warning drivers not to leave their cars unattended without permission and hired Bobby's Auto Repair & Collision to remove cars left on their properties.
Poughkeepsie's towing ordinance requires tow truck operators to wait 20 minutes before removing a vehicle left on private property without permission, unless that vehicle is blocking passageways such as a driveway or interfering with activities such as planned construction or trash removal.
The ordinance also caps tow fees from private lots at $85.
"There are laws on the books that say what he's allowed to charge, and he's charging more than he's allowed to be charging," said John Durso, who owner Bobby Scores charged $243 when his car was towed from a lot on Main Street. "He shouldn't be allowed to do that."
Scores has pleaded guilty in city court at least three times to violating the city's towing laws, and the City Administration has known about the problem for years but has failed to stop it.
7 On Your Side Investigates obtained complaints to the city about Scores' practices dating back to 2015.
Scores also complained to the city about its ordinance during a Common Council meeting one year earlier, in 2014.
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During the meeting, he described the ordinance as outdated and unfair and asked the city to update it.
"It's really hurting my business that I have to stick with $85," he said.
Scores argues private tows shouldn't be held to a different standard than city-ordered tows.
The city of Poughkeepsie charges about two to three times more for vehicle impound fees than the city allows operators pulling cars from private lots to charge.
"I can't even support my family," Scores said. "All I want is the same thing the city gets."
The ordinance also allows for a 20 minute grace period, which Scores argues allows trespassing.
"Let me see a judge come and find a car in his yard," he said. "Let's see how long he waits to tow the car."
Scores added that he believes he's exempt from the ordinance because of a clause that allows exceptions to the rules for vehicles blocking rites of passage, but Poughkeepsie administration has disagreed with Scores interpretation of that clause.
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"That's way too broad," Mayor Rob Rolison said.
Rolison admitted a big part of the problem is the city's own failure to enforce its laws.
The city ordinance requires tow truck operators to maintain a license, but the city hasn't bothered to license any tow truck operators in years -- limiting the administration's ability to levy penalties against Scores.
"The city has not been licensing tow truck operators for a good number of years, which is something that predates me, which is something that needs to be changed," Rolison said. "We need to do that, and we are going to do that."
Rolison also admitted the more-than-15-year-old ordinance needs updating to better reflect the cost of towing today and to clarify the exclusions section of the ordinance Scores has argued leaves him exempt from the city's rules.
"It is something that we are going to address, and it's something we are going to fix because it's not right the way it is right now," Rolison said.
Rolison said the city has established a working group of members of the City Common Council, Police Department, Corporation Counsel and Administration since speaking to Eyewitness News about the problem.
The working group will review the ordinance and propose changes, which Rolison said he expects to see in place by the end of the year.
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