- "Cell 305. Room with a view. Seven minutes, and that's it."
- ―Roy Olsky to Frank Castle
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. When Castle agreed to kill Fisk's rivals within the prison, Olsky facilitated the murder, then, following Fisk's instructions, arranged to have Fisk killed by releasing the inmates in Dutton's wing of the prison.