Roy Olsky is a correction officer at Ryker's Island who was bribed by the powerful inmate Wilson Fisk. Under Fisk's orders, Olsky had Frank Castle taken to Ryker's Island where he could assassinate Dutton before being murdered himself due to Olsky's actions. Although Castle survived, Olsky later assisted Fisk in freeing Castle.
Olsky guarded Frank Castle during his trial at the district court in New York, and guarded him during his transit to and stay in Ryker's Island. When Castle agreed to kill Wilson Fisk's rivals within the prison, Olsky facilitated the murder due to being paid by Fisk, then, following Fisk's instructions, arranged to have Fisk "killed" by releasing the inmates in Dutton's wing of the prison but in actuality Fisk had planned his "death" so that Dutton could be killed by Castle. Olsky told Castle that he has seven minutes to get to Dutton, kill him and leave the prison cell, which Olsky would help him open the door.
However, when Castle went over to the door Olsky was supposed to open he found that Olsky had instead betrayed him by releasing the remaining prisoners loyal to Dutton so that Fisk's remaining enemies would be killed by Castle. When Castle had killed the remaining prisoners numerous correctional officers come in to knock Castle.