Roy Pughsley caught a break last year. The 53-year-old had nearly killed another homeless man with a box cutter inside a River North Walgreens. But instead of going to prison on an attempted murder charge, he pleaded guilty to aggravated battery and walked out with 30 months of probation.
Three weeks later, he was arrested again. And then again. And again. In all, Pughsley has been arrested eight more times since taking that plea deal, according to CPD records, with allegations ranging from possessing a knife to threatening people with knives at Loop businesses. He has repeatedly missed court dates, cycled on and off electronic monitoring and had judges decline to detain him. In his latest arrest, the Cook County Sheriff’s Office linked him to an overnight burglary at the Macy’s flagship store on State Street.
Back in March 2022, Pughsley was on probation for yet another case in which he pleaded guilty to threatening two people with a box cutter after they asked him to leave a bank ATM vestibule near State and Huron streets. Late one night, prosecutors said, he walked into the Walgreens at 641 North Clark Street and started prying on the locked display of shaving products…