No bank robber had ever looked more like a bank president than Harvey Bailey. In addition to his appearance, he also had the reputation – like Pierpont’s lieutenant, Makley – of being able to talk himself out of almost any situation. As soon as he was arrested for complicity in the Urschel kidnapping and placed in a call on the tenth floor of the modern Dallas County Jail, the local newspaper assured its readers that even the ingenious Harvey Bailey could not possibly get out:
SEVEN BARRED DOORS OR GRILLS FACE GANGSTERS IF THEY TRY TO SPRING BAILEY FROM JAIL
The paper went on to say that the few who had escaped before the present system was put into place had done so “through trickery” and officers were “keeping a close eye on Bailey to avoid any such turn of events.”
It took Bailey only two weeks to convince one of his jailers, Deputy Sheriff Thomas L. Manion, to smuggle in saws. Bailey, assuring the jailer that he was innocent of any kidnapping charges, also promised to split the take of his next few bank robberies if he got free.