According to Jay Nash, Bailey was holed up in a separate part of the ranch where Machine Gun Kelly was holding kidnap victim Charles F. Urschel, unaware of the kidnapping and unable to travel because of a bullet wound in the leg sustained during his prison escape.

The marked ransom money was found on Bailey when he was arrested, and he received extra years on his sentence as an "accomplice" in a kidnapping which ironically he had no part of.

He was returned to Leavenworth in 1946 and transferred in 1960 to Seagoville Federal Correctional Institution in Texas, where he remained until he was released on March 30, 1964.

One of the many possible suspects listed as one of the four assassins in the Saint Valentine's Day Massacre is Fred "Killer" Burke.

In 1966, Bailey married the widow of Herbert Allen "Deafy" Farmer and found work as a woodworker in a furniture factory.