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.
Early in the morning of September 4, Labor Day, Bailey – occasionally spelled by his jailer – had almost sawed through the bars. Then Manion brought in a Stillson wrench and a few minutes after 7:00 A.M. Bailey squeezed his big frame through the narrow opening.
Armed with a gun provided by Manion, Bailey took keys from another jailer, walked down to the sixth floor , overpowered a guard and the elevator operator, locked up two jailers, and rode the elevator to the main floor. Here he surprised Nick Tresp, a deputy sheriff. At 7:10 A.M., the two men walked out of the jail to the garage across the street, where Bailey took the first car he saw.
Posses were formed in nearby cities, where roadblocks were set up, and that afternoon, after a hectic chase, Bailey was trapped in Ardmore, Oklahoma. When police handcuffed him to his companion, Tresp indignantly protested, “I’m a jailer.”
Bailey was driven back to Dallas, again put in a solitary cell. His only remark as he reflectively puffed on a cigarette was, “Well, I got out, didn’t I?”
John Toland, The Dillinger Days
You may recall Harvey Bailey as the guy who, upon hearing he was a suspect in the Kansas City Massacre, mailed the lead investigator a letter stating that he could not have been involved because he and his crew were robbing a bank in another state at the time.