The Dillinger Gang and Texas Connections

John Dillinger was a well known gangster who operated in the United States until his death in 1934.  He had been born in Indianapolis, Indiana on June 22, 1903.  Dillinger’s mother died when he was three years old and he was raised by his father and stepmother, with whom he is said to have had a difficult relationship.  The family moved around somewhat and Dillinger dropped out of school.  Around 1923, he joined the United States Navy.  He was assigned to the U. S. S. Utah but only served a short while before deserting, after which he launched his criminal career.  Not long afterward, Dillinger was arrested, tried and convicted for a 1924 robbery of a local grocery in his adopted home town of Mooresville, Indiana and was sentenced to the Indiana State Prison.  There he was exposed to fellow convicts including a number who had been bank robbers.  Upon his parole in the spring of 1933, he and several associates began to commit a series of bank robberies in Indiana and Ohio.

In the fall of 1933, Dillinger was captured in Ohio and put in jail, only to be rescued by several individuals that he had himself helped escape from the Indiana State Prison.  The escape resulted in the death of a local sheriff.  The gang resumed robbing banks in Indiana and Wisconsin before fleeing to other parts of the country.

During this period, the Dillinger gang was suspected of killing a San Antonio, Texas detective by the name of Henry Perrow.  Detective Perrow had been alerted to the possible presence of a “Chicago” gang in the city.  On December 11, 1933, he and fellow officers had been trailing a suspicious individual who was traveling around town in a taxicab.  They pulled alongside the cab and tried to talk to the suspect who then bolted out of the cab and fled on foot, followed by the officers.  Perrow and his fellow officers trailed the man to an alley with no exit after which the suspect drew two pistols and fired on the officers.  Perrow received a fatal wound to his head and another officer was wounded.  The assailant was later identified as Tommy Carroll, a Dillinger associate who was believed to be in town to purchase Thompson submachine guns and other modified weapons from a local gunsmith named H. S. Lebman.  Detective Perrow was 56 years old and had been a law officer for fifteen years at the time of his death.  He is interred in San Fernando Cemetery #3 in San Antonio, Texas.  The suspect Carroll was killed in an unrelated shootout the following year.

Dillinger and some associates were arrested in Arizona and extradited to Illinois, but upon being jailed in Illinois, again he escaped.  He had fashioned a fake pistol out of a piece of wood, blackened with shoe polish.  He resumed robbing banks with an array of associates.

Dillinger was finally killed after he was betrayed by an informant in Chicago.  Division of Investigations (prior to the agency being renamed the Federal Bureau of Investigation in 1935) director J. Edgar Hoover had created a task force to locate Dillinger and his associates.  The accounts state that in July of 1934, Ana Cumpănaș, also known as Ana Sage or the “woman in red,” contacted the investigators about Dillinger’s whereabouts in an effort to prevent her deportation.  She was a known brothel operator and the authorities had sought to deport her for her activities in the sex trade.  She told the investigators that Dillinger was going to be attending a movie the evening of July 22, 1934 in Chicago at one of two theaters and that she would be wearing an orange dress or skirt to help them identify him.  Dillinger and companions entered the Biograph theater and watched the film (ironically, it was the George Cukor-directed crime film “Manhattan Melodrama” starring Clark Gable, William Powell and Myrna Loy) as investigators staked out both theaters to apprehend the outlaw.  As Dillinger and his party were leaving the theater, the outlaw spotted the officers and attempted to draw his own gun.  He was then shot four times: several less serious wounds and a fatal wound to the head.  Dillinger, who was believed to have killed around a dozen individuals and wounding nearly as many more during his relatively short criminal career, likely died at the scene but was transported to a hospital where he was officially pronounced dead.  His body was placed for public viewing in the Cook County, Illinois morgue.  After a funeral, he was laid to rest in Crown Hill Cemetery in Indianapolis, Indiana.

One of the lead investigators in the case (working under Chicago Bureau Chief Melvin Purvis) was Charles Winstead, born in Sherman, Texas.  Winstead had previously been on the task forces assigned to locate the Barrow gang “Pretty Boy” Floyd and “Machine Gun” Kelly, in addition to being assigned to the Dillinger investigation.  Winstead had been born in Texas in 1891.  He served in the United States Army in World War I.  After leaving the Army, he had served as a deputy sheriff and as an investigator for the United States Attorney’s Office in Texas before joining the Department of Investigations in 1926.

Winstead fired his service weapon in the Dillinger incident, as did other officers.  He has been credited for firing the fatal shot that killed the outlaw.  Another officer named O’Neil was also credited for the shot.  Winstead eventually left the Department in late 1942 due to a disagreement with Director Hoover.  He then served in Army intelligence and security during the latter years of World War II, reportedly for some time in Los Alamos in connection with the Manhattan Project.  After the end of World War II, he worked at a number of jobs before becoming a deputy sheriff in Albuquerque, New Mexico where he was living when he died at the age of 82.  Winstead is buried in Fairview Memorial Park in Albuquerque, New Mexico.

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