Frank Boles

Frank Boles has been working at Arkham Asylum for eight years. He has twice been suspended for drinking on the job and regularly holds poker evenings in the guard rooms. Frank is desperate to be top dog at Arkham, which he thinks he is already; he fails to recognize that he is considered untrustworthy and generally disliked.

Batman: Arkham Asylum
After having Joker help him out of a previous situation, 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 James 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 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.