Throughout history, America’s obsession with outlaws is almost as strong as its love of baseball. While not necessarily condoning their illegal activities, the exploits of those like Billy the Kid, Jesse James, and myriad of others have captured the attention of many. John Dillinger, the notorious bank robber from the 1930’s is part of that group, catapulted to infamy when the FBI named him as their initial “Public Enemy Number One” on June 22, 1934. While certainly not the sole reason, there is abundant evidence that suggests Dillinger’s connection to baseball may have contributed to his life of crime.
Dillinger was born on June 22, 1903 in Indianapolis. His father owned a small grocery store and rented out several homes in the area. Dillinger’s mother died when he was three and he was primarily raised by an older sister until his father remarried when John was nine. He was in frequent trouble as a child, leading a neighborhood gang called the “Dirty Dozen,” which did things like stealing coal from rail yards. Despite his burgeoning criminal career, he, like a majority of American youth at the time, adored baseball, and played as frequently as possible.
As he reached adulthood, Dillinger continued to find trouble, joining and deserting the Navy in 1923, not being able to take the strict regimen. In 1924 he married a 16 year old girl, and shortly thereafter was arrested for stealing 41 chickens, but his influential father helped keep him out of jail. Despite trying to settle down, he had little direction in his life, but still loved baseball.
Dillinger participated in the common pastime of town ball, playing on teams associated with his community and earning a reputation as a star second baseman and pitcher, even earning a $25 bonus from a local furniture store for being the best hitter on the Martinsville, Indiana team. Many claimed that he had the skills to be considered for professional team. Unfortunately, he never got that opportunity.
Despite the structure of baseball, Dillinger only furthered his venture into crime while playing town ball. Two other members of the league helped cement his life on the wrong side of the law. One of his teammates, Harrp “Pete” Pierpoint, was his first true partner in crime, assisting in a number of heists over the years. Dillinger’s cousin, Edgar Singleton, a man nearly twice his age, was an umpire in the league and gave Dillinger the final push into a full time life of crime.
When the 1924 baseball season ended in August, neither Dillinger nor Singleton had jobs or prospects. On September 6, 1924, they robbed a Mooresville, Indiana grocery store. Dillinger beat the grocer with a cloth-wrapped iron bolt, but fortunately didn’t severely hurt the man. Singleton had cased the job, convinced Dillinger to participate, and acted as the getaway driver. The two bandits were caught shortly after the robbery and held over for trial.
Although Singleton was older and had a record, he received only a 2-14 year prison sentence, in contrast to the young Dillinger, who was given the maximum 10-20 year sentence, to be served in the Indiana State Reformatory in Pendleton. Dillinger was considered a low-risk prisoner, with only minor reprimands while at Pendleton. He worked in their shirt factory and continued playing baseball as a member of the prison team. He was also involved in prisoner baseball pools and kept up with the progress of the Chicago Cubs, his favorite team.
Dillinger first became eligible for parole in 1929. On the day before his parole hearing, he played in a prison baseball game in front of Indiana governor Harry Leslie, who was to help review his case with the parole board. According to John Toland, author of The Dillinger Days, Dillinger played so well that the governor told reporter, “That kid ought to be playing major league ball.” However, the criminal’s exploits on the diamond were not enough to earn him any favors, and the next day his parole was denied.
Dillinger stewed over the board’s decision; convinced that his parole was denied because the Indiana State Prison in Michigan City, the largest prison in the state, wanted him to play shortstop for their baseball team. He had heard that they had inquired about him transferring to their facility and playing with their team, which he believed was a sign of how much they wanted him. Baseball was so entrenched as the national pastime, that competition flourished in even the most unlikely of places, making Dillinger’s theory not totally implausible.
Dillinger’s belief that he was coveted by the Michigan City baseball team grew stronger when he was officially transferred there in 1930. He rebelled by declining to play, and became depressed after realizing he was in a much more restrictive facility than before. In a 1930 letter to home, he wrote, “Well, baseball season is nearly here but I don’t care to try for the team here although I love to play, if I hadn’t played on the team at the reformatory, I don’t think I would have been sent up here; and I’m sure I would have made a parole there this winter, so you can see why I am not so enthusiastic about making this team.” Instead he bided his time associating with hardened criminals and learning even more tools of their trade.
Dillinger finally obtained his release in 1933. Almost immediately he came to national attention because he began robbing banks after playing a prominent role in helping 10 prisoners escape from Michigan City, including his old baseball teammate, Harrp Pierpont. After the FBI targeted Dillinger as the top priority he became one of the most famous people in America almost overnight. Despite the increased scrutiny, he still kept up with his beloved Cubs. He was believed to have attended several major league games during his most-wanted days, including one between the Cubs and Dodgers at Wrigley Field on June 26, 1933. Eye-witness Robert Volk later claimed that Dillinger sat beside him in the bleachers before leaving during the seventh inning stretch.
Dillinger’s lifestyle meant it was only a matter of time for him to be able to stay ahead of the law, and it all came to an end on July 22, 1934, when he was shot to death while exiting a movie theatre. The most famous criminal in the world at the time died at the age of 31.
In retrospect, Dillinger’s connection to baseball was a major factor in plotting the course of his life. If he had pursued playing professionally, he may have had a chance at a normal life. As it was, the associates he made while playing in a semi-pro league helped turn him from a troubled youth into a hardened criminal. Additionally, while in prison for the first time, his ability on the baseball diamond may have dramatically impacted any chance he had at rehabilitation. Prison officials may have been more interested in having him improve their teams rather than considering the impact the system was having on the young man. Regardless, it is clear that baseball had a deep and profound effect on one of the most famous criminals the country has ever known.