When the Dillinger Gang Came to West Terre Haute

Charles Makley indiana prison

In January 1934, at the height of the gangster era, no one was more famous than Hoosier brigand John Dillinger. Newspapers, the radio, and newsreels breathlessly followed his exploits. During the Great Depression, that period of foreclosures, lost jobs and hunger, gangsters like Dillinger were often portrayed as modern Robin Hoods. Of course, this was pure romanticism. Though they may have stolen from the rich (or at least their banks), they seldom gave back much to the poor.

John Dillinger, Hoosier

John Dillinger, Hoosier

Dillinger was one of those who became a folk hero. Known for his cool and polite manner as he robbed terrified tellers, Dillinger earned his reputation as Robin Hood for deeds such as refusing to take the few dollars a poor farmer had on him when he was unlucky enough to be in a bank that Dillinger was robbing. A real gentleman, that John Dillinger.

From Mooresville, Indiana, Dillinger had connections to West Terre Haute. While in prison for a small time robbery in his youth, met one Russell “Boobie” Clark in the state pen at Michigan City. Clark, a Vigo County native, had already made a shady name for himself. After being dishonorably discharged from the Marines following WWI, Boobie, like so many others, took advantage of the opportunities offered by the foolish and ill-fated social experiment known as Prohibition.

Clark became involved in bootlegging. As a bootlegger he knew where all the speakeasies and “illicit” roadhouses were located. When just acting as middleman in the illegal liquor was not remunerative enough for Boobie, he began to rob the joints. In 1926 he was suspected of kidnapping two bootleggers from West Terre Haute and killing another in Danville, Illinois who was apparently out of favor with Cicero (Al Capone Territory) bootleggers. It was after these escapades that Clark was sentenced to Michigan City. There he met Dillinger and veteran bank robber like Charles Makley.

Starting in 1933, after his release, Dillinger began a brief and meteoric career as a bank robber. There was no one Dillinger Gang. Dillinger changed partners with the promiscuity of a Hollywood starlet. Many criminals moved in and out the “gang,” but Clark and Makley were stalwarts.
The new year 1934 was barely born when Charles H. Ray found out that the Dillinger Gang was casing his State Bank of West Terre Haute as a juicy target. On Saturday, January 6th, Ray was visited by Ivan Herring. Herring was West Terre Haute’s town Marshal. Evidently, Ivan was more well connected to the doings of the criminal element than most small town Marshals, for he had gotten word that members of the Dillinger gang were going to rob the bank of its Monday payroll funds. Herring had a snitch, whose identity he would not reveal as it would mean a “ride” for the underworld tattletale.

Astounded and fearful, Ray contacted another banker named Howard Derry, who arranged for the bank president to meet with Terre Haute Chief of Police Armstrong. Word that the Dillinger gang was near was a call to action and a plan was put in place.
It was decided that Ray would appear to pick up the funds from a bank in Terre Haute on Monday as usual. The Terre Haute police car would follow surreptitiously and foil the robbery. Charles Ray returned home to spend an anxious weekend.

Monday morning January 8th, he drove to the bank on Wabash Avenue, went inside and came back out with a “dummy” package of money. At about 8:30 Ray did a u-turn on Wabash Avenue, dodging street cars, and headed toward West Terre Haute. In his rearview mirror he saw the Terre Haute police car.

As he crossed the Wabash River bridge it all became too real for him. Waiting on the bridge was a Ford V8 (Dillinger’s gang preferred high-powered cars like that or Hudson Terraplanes, usually stolen, as getaway cars) with Ohio license plates. It was exactly the type of car Herring had told them the robbers would be driving. At least two men (three men was considered the minimum for a successful bank robbery: one to be the getaway driver, one to be a lookout, one to do the actual robbery) were in the car. The car began to follow Ray.
As Ray drove over the grade, he looked back one more time. To his astonishment, instead of following behind both cars, the Terre Haute police car sped up and insinuated itself between the bank president’s car and the robbers’ Ford. He “wondered why they [Terre Haute police] didn’t drop back, but supposed it was part of the plan.”

Hudson Terraplane, preferred getaway car of Dillinger.

Hudson Terraplane, preferred getaway car of Dillinger.

Bewildered, Ray drove on to his bank on Paris Avenue. He parked, looked around and hurried into the bank with his dummy package. When nothing happened Ray went out to the police car parked next to the bank.

Leaning into the car he asked the policemen what had happened to the Ford with Ohio plates. Looking confused, the police said “They didn’t know but would try to find it. They had been sent out with no instructions. It was awful.”
Finally, the police said they would try to find the robbers and sped off, They thought they were in luck when they spotted the car parked by the clay plant on the western edge of town. But as they approached tommy guns were thrust out of the Ford’s window as a warning and the car began to hurtle along the National Road to Illinois. The police car got “snarled in traffic.” The chance was lost.

Ray and the police then tried to figure out what had gone wrong. Again they said they did not have instructions on how exactly to foil the robbery plot. Three robbers had been in the car. Dillinger and Clark were not among them, but they identified known gang members named Burke and Burt. Evidently hiding on the floor of the back seat along with his trusty Tommy gun was Charles Makley.
Makley, known as Fat Charley, had spent Christmas in Florida with Dillinger at a gang hideout. They had a merry Christmas and exchanged gifts like jewly and a puppy for Dillinger’s girlfriend. After the failed robbery in West Terre Haute, Makley and the other gangsters continued west to a gang hideout in Arizona.

"Fat Charley" Makley

“Fat Charley” Makley

That Monday night, Charles Ray noted in his diary that “Ivan knew the story. Our plan was perfect, but because police headquarters didn’t give the squad they sent out any information they missed a great chance” to capture some of the Dillinger gang.

One must wonder if the failure was due to ineptness or a tip from an informant in the Terre Haute police that warned the gang of what might happen?

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Footnote:  I recently interviewed a man who averred that his uncle was familiar with John Dillinger.  He said his uncle encountered Dillinger in a speakeasy on South First Street in Terre Haute.  During the “visit” Dillinger, tommy gun close at hand, joked he would never rob a bank in Terre Haute because he “was sure to get railroaded” as he attempted to get away.  Dillinger was known to have spent some time in Terre Haute in October or November, 1933.

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