This is a vintage postcard, circa 1927, of the Indiana State Prison at Michigan City, Indiana.  The image depicts how the prison appeared when Pete Pierpont, Homer Van Meter and John Dillinger were inmates there. Vintage postcard, circa 1927.  Image online, courtesy Michigan City Public Library.


Serving time at Indiana’s Pendleton Reformatory, John Dillinger met Harry (“Pete”) Pierpont and Homer Van Meter.  Both men would play key roles in John’s future career. 

Known as a handsome man with gray eyes, Pierpont had a normal childhood until he was hit on the head with a baseball bat.  Thereafter, various incidents caused his mother to say her boy was mentally unstable.  When it came to thinking about escape from his ten-to-twenty-one-year bank-robbing sentence, however, Pierpont kept a pretty clear head.

Van Meter followed a different path.  A runaway at eleven, he worked in Chicago as a bellhop.  At seventeen, he was convicted of stealing a car.  After his parole, a year later, he and a buddy robbed passengers on a  train.  A Pendleton official was worried about Homer:

This fellow is a criminal of the most dangerous type.  Moral sense is perverted and he has no intention of following anything but a life of crime ... He is a murderer at heart, and if society is to be safeguarded, his type must be confined throughout their natural lives.

While at Pendleton, Dillinger (who loved baseball) played on the reformatory’s team.  After Pierpont and Van Meter were transferred to Indiana State Prison at Michigan City, John missed his pals. 

In another life-changing event, Johnny convinced Pendleton’s officials to let him play ball on Michigan City’s team.  He was soon transferred to that facility, then home to mature and hardened bank robbers.

In mid-1932, Pierpont began to plan a prison break—with weapons.  Talking with Charles Makley (serving fifteen years for a 1928 bank job), Russell Clark (serving twenty years for a 1927 bank robbery) and John (“Red”) Hamilton (serving twenty-five years), Pierpont believed the men had everything they needed—except the guns. 

Someone on the outside needed to smuggle-in weapons.  But ... how would that happen, and ... who would it be?

One prisoner, who kept requesting parole from a sentence everyone believed unjust, seemed a good choice.  Not long before Dillinger’s many efforts (and those of his family and the grocer he’d mugged) legally unlocked his prison cell, John talked with Pierpont.  Those were fateful discussions.

The man with everything to gain from a prison break convinced the man with everything to lose to provide escape weapons.  In exchange, Dillinger would become a member of Pierpont’s gang.

By the time he left the Michigan City prison—on the 22nd of May, 1933—Dillinger knew what he would do.  It took him three months to make, and execute, his plan. 

During September of 1933, after Pierpoint’s parole request was denied, John Dillinger helped ten prisoners escape by secretly packing several guns into thread boxes.  (The inmates worked in the prison's shirt factory.)  

Despite his helpful assistance, Dillinger was not personally present during the Michigan City break.  He'd been arrested in Allen County, Ohio and was there—in Lima—when his pals used real and fake guns to leave the Indiana State Prison.

The Michigan City escapees did not walk away unscathed, but those who survived soon engineered another jail break. After all, they needed to thank Dillinger for his help.

On the 12th of October, after mortally wounding Jess Sarber (the Allen County sheriff) in front of the lawman's wife, Johnnie's friends unlocked their pal's cell. 

Dillinger was now on a path to become America's "Public Enemy Number One."

0 Question or Comment?
click to read or comment
2 Questions 2 Ponder
click to read and respond
0 It's Awesome!
vote for your favorite

Author: Carole D. Bos, J.D. 5197stories and lessons created

Original Release: Jul 01, 2009

Updated Last Revision: Jul 08, 2019

To cite this story (For MLA citation guidance see easybib or OWL ):

"JOHN DILLINGER AND HIS FRIENDS" AwesomeStories.com. Jul 01, 2009. May 30, 2020.
Awesome Stories Silver or Gold Membership Required
Awesome Stories Silver or Gold Membership Required
Show tooltips