During the Prohibition era, Harry Pierpont was a gangster with a long rap sheet of crimes. With natural leadership skills and handsome face, Pierpont was loyal to his criminal friends. He preferred to stay out of the spotlight and didn’t care if others took credit for the brash bank robberies that he participated in. Most notably, Pierpont was a friend and mentor of the infamous John Dillinger.
Throughout the 1920s, Harry Pierpont robbed banks and hardware stores, carried concealed weapons, stole guns, and assaulted some of his victims. His downfall came when he and other members of his gang, including John Dillinger, wound up in Tucson, Arizona. They were careless in their actions when they arrived in town and the gang made several minor blunders that led to them being identified and captured.
All of the gangsters and their girlfriends were extradited back to the Midwest to stand trial. It was the testimony of a former gang member that helped convict the gangsters. In early March 1934, Harry Pierpont and other members were convicted of killing a sheriff. Pierpont got the death penalty.
While on death row, Pierpont and others devised a plan to break out of jail by carving fake pistols out of soap. They were successful in getting out of their cells with the false weapons and even made it to the main door of the death house before they were met with guards that opened fire with their rifles. Pierpont was shot more than once, but he survived. When he was executed in the chair on October 17, 1934, he was still seriously wounded. Pierpont died at the Ohio Penitentiary at the age of 32 years old.
Louis “Lepke” Buchalter
Louis “Lepke” Buchalter is known as a mobster and head of the Mafia hit squad nicknamed Murder, Inc, which was active during the 1930s. When Dutch Schultz made a request to the Mafia Commission for permission to kill his enemy, Thomas Dewey (a U.S. attorney), the Commission decided that it was best to kill Schultz instead. Buchalter put an immigrant named Albert Anastasia in charge of assassinating Schultz.
In 1936, Murder Inc. killers acted upon Buchalter’s orders and gunned down a Brooklyn businessman named Joseph Rosen. Because of this amongst other crimes, Buchalter became the only major mob boss sentenced to the death penalty in the United States. When he was convicted, it took place on December 1941. When the New York Court of Appeals reviewed his case, they upheld the conviction and his death sentence in October of 1942. Buchalter was successful in prolonging the process of execution by remaining in Kansas until January of 1944. He was finally extradited to Sing Sing and was executed on Saturday, March 4, 1944 by the electric chair.