Oswego man arrested 18 times over span of 4 days, police chief and mayor say it shows systemic issue

Local News

OSWEGO, N.Y. (WSYR-TV) — Robert Updegrove was arrested 18 times within just four days. Charges included stealing, harassing, resisting arrest and trespassing.

On all but one arrest, Updegrove was released on an appearance ticket, which is something the Oswego mayor and the city police chief don’t agree with.

“Somebody who is committing these crimes over and over and over again 18 times in four days is not somebody who should be turned loose to go do it again and go threaten the people that made the call, made a 911 call not two hours ago.  So, this just points out a real flaw in the system,” said Oswego Mayor Billy Barlow. 

The system is broken. It wasn’t great prior to bail reform but they haven’t corrected most of the issues that they’ve needed to correct.

Chief Phillip Cady, Oswego City Police

For Chief Cady and his officers, a situation like Updegrove’s puts a real strain on the department and city’s resources.

“He urinated in the station, so we have to bring cleaning staff in to take care of a hazard. So, it’s not just the complaint, it’s not just the time involved, it’s keeping us from being able to work and handle other complaints,” Chief Cady recalled. 

Over those past 4 days, Updegrove committed most of his crimes at convenience stores across the port city. The police chief and the mayor actually said he’s banned from an Oswego Byrne Dairy, Stewarts, and most recently, not allowed near certain hospital staff members.

“He’s turned his back on many of the service providers that are there to help him,” said Chief Cady.

Chief Cady and Mayor Barlow hope that a re-evaluation of the laws can ultimately help the city.

Updegrove is held at the Oswego County jail after his 18th arrest for burglary and larceny.

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