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In 1953, Ryan and Mulkahey encountered Benny Russell outside the offices of Incredible Tales of Scientific Wonder and began harassing him. Ryan gave Russell a hard time about his suit, wondering how a black man could afford a nice one. He also took Russell's drawing of Deep Space 9 before giving it back to him and finally allowing him to go. Ryan wanted to arrest Russell, but Mulkahey was not as interested.
Ryan and Mulkahey were later responsible for the death of Jimmy, a young criminal and acquaintance of Benny. At the time of Jimmy's shooting, Russell tried to help him but was forcibly restrained by Ryan and Mulkahey, receiving a severe beating in the process. (DS9 episode & novelization: Far Beyond the Stars)
In December of that year, James Wykoff requested Russell's police record from the New York Police Department. The report stated that Russell had attacked the police officers and brandished an offensive weapon. (DS9 - Strange New Worlds IV short story: "Isolation Ward 4")