Before the game even begins the Joker helped Frank from some previous situation. After the Joker help Frank, Boles ultimately finds himself embroiled in Joker's latest scheme to rid Gotham of the Dark Knight, helping him break free upon entering Arkham right under the nose of Batman. Boles is also instructed to kidnap Commissioner Gordon, to whom he brings into the care of Harley Quinn. Using his knowledge of Boles' past, however, Batman is able to pick up traces of Boles' favourite tipple on the Arkham air and follows it in the hopes that it will lead him not only to Boles but to Gordon himself.
Batman tracked Boles through the Intensive Treatment Center, where Boles betrayed William North and several other Arkham security guards, attempting to draw them away to the front entrance. As several of the guards moved for the exit, Boles shot them dead. With the help of Harley Quinn and an army of Blackgate Prisoners, Boles secured the front entrance of the Intensive Treatment Center.
When Batman eventually did reach the end of the trail to Boles, he finds that the Joker is aware of his actions, also Boles is no longer useful, and has already had the corrupt guard murdered. Frank has been strapped to a prisoner movement handcart with a green smile painted across his mouth and a sign reading "Dead End" chained around his waist, when found by Batman.
- "Shut it clown, a lot people of here want to talk to you!"
- "Whatever, just be quick!"
- "I thought I told you to be quiet!"
- "Joker's got more men on the way. They're coming around the front of the asylum. Gotta stop them from getting it! Quick! Get over there! Dammit everyone, cover the main entrance!"
- "Quinn! It's clear! Get your ass in here!"