While incarcerated at Indiana State Prison, Makley became part of a group of inmates planning a coordinated escape. When Dillinger was paroled in May 1933, he began executing the escape plan from the outside, robbing banks to finance the operation and smuggling weapons into the prison. On September 26, 1933, Makley and several other inmates escaped from Indiana State Prison using smuggled weapons. The group immediately began a crime spree across the Midwest, with Makley serving as one of the gang's primary leaders.
Gambier bank robbery On October 6, 1933, Makley led a robbery of the Peoples Bank in
Gambier, Ohio, while Dillinger was incarcerated in the county jail in
Lima, Ohio, awaiting trial for a bank robbery in
Bluffton, Ohio. During the Gambier robbery, the bank's cashier, J.R. "Ray" Brown, engaged the robbers in a gunfight and was shot in the hand. The gang seized Brown and used him as a human shield during their escape, making off with $714. Brown was later released unharmed at the bottom of College Hill, just outside Gambier. Makley was identified as the actual leader of this heist by both Brown and
Kenyon College student J. Grant Dwyer, who was a customer in the bank during the robbery. This crime marked Knox County's first-ever armed robbery of a bank.
Lima jail break Less than a week after the Gambier robbery, on October 12, 1933, Makley participated in the infamous Lima jail break that freed Dillinger. The FBI identified Makley as one of four men who showed up at the Lima jail claiming to be returning Dillinger to Indiana State Prison for parole violation. When the sheriff asked to see their credentials, one of the men shot and killed Sheriff Jess Sarber. The successful jailbreak reunited the core members of what the press would dub the "
Dillinger gang." ==Capture and trial==