May 19, 2021

How bail reform allowed homeless Oswego man to be arrested 15 times in 4 days before going to jail

How bail reform allowed homeless Oswego man to be arrested 15 times in 4 days before going to jail

Oswego, NY — A homeless Oswego man spent four days earlier this month getting arrested on minor crimes — mainly criminal trespassing — before getting ticketed and let go in a cycle that repeated itself 15 times before a judge was finally able to jail him.

By then, Robert Updegrove, 32, had amassed a total of 23 separate charges — all but one of them non-violent misdemeanors or violations.

None of them were eligible for jail under the state’s bail reform law.

Updegrove was jailed May 12 after being accused of taking things just a bit further than before, giving police an opening to bring him before a judge. Even though he still hadn’t been charged with a bail-eligible offense, a judge used leverage from a prior case to lock him up on $10,000 cash bail, according to court records.

Updegrove remains jailed as of Tuesday, according to public records.

Updegrove’s situation was first spotlighted by Oswego Mayor Billy Barlow, who blamed the state’s bail reform law for the extraordinary number of arrests without jail.

“Mr. Updegrove’s long arrest record clearly demonstrates how flawed New York State’s so-called “Bail Reform” laws are and how the changes simply empower criminals, hinder law enforcement, absorb valuable resources and leave law-abiding citizens in real danger,” Barlow said in a news release, after highlighting Updegrove’s case on social media.

The mayor is correct that the state’s bail reform law made it much easier for Updegrove to be arrested so many times in such a short period. That’s because the majority of his charges were criminal trespass complaints — a Class B misdemeanor considered the lowest level of crime in the state’s penal law.

Before bail reform prohibited a judge’s oversight in those cases, Updegrove could have been brought to court and jailed on a low amount of bail. That wouldn’t have automatically prevented Updegrove from posting bail (misdemeanors rarely result in much bail) and being arrested again, but it would have almost certainly slowed him down, if he could make bail at all.

In the repeated criminal trespass cases, Updegrove had been warned to stay away from numerous places, including several popular businesses, the city’s hospital, an addiction clinic and a laundromat, but returned without permission, often acting erratically, police said.

The main reason Updegrove wasn’t jailed earlier is because none of his arrests during those four days were considered violent: he possessed no weapons during his cycle in and out of police custody and he was never charged with assaulting or threatening anyone. Allegations of weapons or physical harm would have likely made him eligible for jail under the bail reform law.

Perhaps the closest he came to seeing a judge before his eventual jailing May 12 came two days earlier (his fifth arrest), when he was arrested for trespassing at Oswego Hospital. The hospital’s emergency waiting room had an order of protection that kept Updegrove away when he wasn’t there getting medical treatment, and he was arguably in violation at that point.

But Updegrove had been transported to the hospital for legitimate medical treatment, before refusing to leave when his medical reason for being there had ended, said Oswego police Lt. Damian Waters. It’s unclear whether that would have been an actual violation of the order of protection, he said.

The rest of the charges were clearly ineligible for bail under the state’s 2019 law, which prohibits virtually all misdemeanor and non-violent felony charges from resulting in jail before trial. For misdemeanors, it’s unheard of to even bring a suspect before a judge (short of a sex crime or a domestic violence situation). So Updegrove was repeatedly ticketed and released for his misdemeanor charges, only to be re-arrested, sometimes hours later.

That cycle of catch and release ended the afternoon of May 12 when Updegrove faced his first felony during his arrest spree.

In that case, Updegrove was accused of trespassing at a Byrne Dairy on West Bridge Street for the sixth time in four days. But this time, he was accused of stealing an alcoholic beverage. Under state law, unlawfully entering a property to commit a crime is felony burglary.

That gave police an opening to bring Updegrove before a judge on the afternoon of May 12. That’s despite the fact that third-degree burglary itself wasn’t eligible for bail — though a felony, it wasn’t a violent felony.

Once in court, Updegrove’s past arrest came back to haunt him. In April, he’d been accused of threatening people inside the Oswego Hospital emergency room with a “broken portion of a fiberglass pole” that was likened to something that would hold up a camping tent. The pole was wrapped in electrical wire, according to police.

That wasn’t Updegrove’s first criminal weapon charge. And so he faced a third-degree illegal weapon possession — a violent felony — from that April 2 incident. That’s a charge eligible for bail.

At the time of his April arrest on that charge, a judge had released Updegrove on his own recognizance. But after Updegrove was brought back to court following the days of arrests, the judge changed course: bail on the April case was now set at $10,000 cash or $100,000 bond, according to court records.

And that’s how Updegrove eventually landed in jail, where he remained Tuesday.

From May 9 to 12, Updegrove’s charges included:

  • Six criminal trespass charges, as well as one burglary and one petit larceny charge, at the Byrne Dairy, 97 W. Bridge St. (In the last incident, he’s accused of stealing an alcoholic beverage.)
  • Two criminal trespasses at the Victory Center (drug rehab), 225 W. 1st St.
  • Two criminal trespasses at the Stewarts Shops, 51 W. Utica St.
  • One petit larceny at Paul’s Big M, 276 W. 1st St. (A soda and junk food were stolen, police say)
  • One criminal trespass the Colonial Laundromat, 65 E. Bridge St.
  • One criminal trespass at the Oswego Sub Shop, 106 W. Bridge St. (He’s accused of rummaging through their trash cans)
  • One criminal trespass at the Oswego Hospital emergency room. (He had been taken there for treatment, but refused to leave afterward, police say)
  • One criminal trespass at a house owned by the Victory Center at 52 E. Seneca St.
  • Three resisting arrest charges from separate incidents, including pushing away from officers and fleeing. No acts of violence against officers alleged.
  • Three criminal tampering charges, accused of spitting and urinating while in police custody on separate occasions.

Staff writer Douglass Dowty can be reached at or 315-470-6070.

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