How bail reform allowed homeless Oswego man to be arrested 15 times in 4 days before going to jail Updated 9:26 AM; 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.