Short was reputed to be Stone County's biggest bootlegger, but until 1933, about the worse trouble he'd ever been in was an unproven charge of selling illegal whiskey in the late 1920s. After the Bank of Galena was held up by three men on August 28, 1933, though, Short was arrested and charged with being an accessory for allegedly having met with the perpetrators. Promptly released on bail, Short swore there was nothing to the charges against him, and he went on promoting an upcoming boxing match. The charges against him were subsequently dropped when it was determined there was insufficient evidence against him to warrant a trial.
Short was soon in trouble again, though. In January 1934, he was re-arrested and charged with being an accessory to an October 1933 robbery of the Model Bakery in Springfield. It was alleged that Short was the "brains" of the stickup job. At his trial in March 1934, Short was convicted of conspiracy in the robbery and sentenced to ten years in prison. He was released on bond while he appealed the conviction, and while still out on bail he was implicated in yet another robbery--the holdup of the Bank of Billings in December of 1933. It was about this same time, the spring of 1934, that it was first alleged that Short was part of an organized gang of thieves and robbers. Although certain other members of the gang, such as Dewey Gilmore, were also tentatively identified, neither Short nor Gilmore had yet come to be associated with the Irish O'Malley gang, as they later would be. In fact, the O'Malley gang did not come to public attention until late May of 1935.
Meanwhile, Short was arraigned in Christian County in connection with the Billings bank robbery and was released on $25,000 bond. One justice declined to bind Short over to the circuit court on the charge because of the dubious character of the primary witness against him, who was an ex-convict. However, the charge was refiled with another justice, who did bind the defendant over for trial in the circuit court. When the case came up at Ozark in late May, Short was granted a change of venue to Douglas County.
As Short's legal troubles mounted, he discontinued his promotion of boxing and wrestling matches at the Shrine Mosque and returned to his title business in Galena. At his September trial in Ava on the Billings bank robbery charge, several members of Short's family testified that he was with them at the time he was supposedly meeting with the holdup men, and the jurors acquitted Short after just fifteen minutes of deliberation.
In November 1934, Short and a couple of other men were arrested as "suspicious characters" because they were "parading the business district of Monett in a motor car," as if they were casing the town. Although the car was found to have a "large arsenal" of weapons in it, Short was released after questioning.
Then on January 3, 1935, Short and several other men were arrested when Bob Johnson, fleeing from a shootout at Picher, Oklahoma, was captured in Stone County. He led authorities to a stash of stolen goods and implicated the other men in a series of gunfights and robberies in southwest Missouri and northeast Oklahoma in recent months. Short was charged, in particular, with complicity in a recent diamond robbery in Jasper County, and he was taken to the lockup in Carthage. The next day, he was also implicated as an actual participant in the robbery of the Bank of Crane on January 1.
As usual, Short was released on bond pending trial, and while out on bond he was arrested for allegedly participating in the burglary of a Nixa filling station on the night of February 16. A week later, the charge was dropped after the complaining witness dropped his complaint, saying he was not sure of his identification of the suspect. Somewhere about this time, Short closed his title business in Galena, apparently to concentrate on outlawry.
In late May, Short was tied to the Irish O'Malley gang after Dewey Gilmore was arrested in Texas and Walter Holland, alias Irish O'Malley, was arrested for an alleged kidnapping in Illinois the previous August. Short was among other gang members rounded up, and he was implicated, along with Gilmore and others, in the double robbery of two Okemah, Oklahoma, banks on December 22, 1934. The same gang was suspected in several other bank robberies as well, including one at Fort Smith less than a month before the arrests and one at Neosho two months before that. One officer remarked that the arrest of the O'Malley gang members cleared up virtually every bank robbery throughout the Midwest over the previous couple of years.
After his arrest, Short was also linked to the Six Daring Bandits, another gang that was broken up near the same time as the O'Malley gang. For instance, the Crane bank robbery was generally attributed to the Six Daring Bandits.
Short was transported to Oklahoma and jailed at Muscogee to await trial on the Okemah robberies. While he was still awaiting trial, he lost his appeal in the Springfield bakery holdup case and was ordered to serve his ten-year sentence. Authorities in Oklahoma would not release Short to Missouri, however, until after his trial on the Okemah bank jobs. In late November, he was found guilty in federal court of complicity in the Okemah crimes. On December 3, however, before he could be sentenced, he and three of his comrades in the O'Malley gang, including Dewey Gilmore, broke out of the Muscogee jail where they were being held, seriously wounding a lawman in the process. Three days later, they were trailed to a farmhouse near Claremore, where lawmen engaged them in a shootout when they refused to surrender. One outlaw was killed outright, Short was mortally wounded and died within hours, Gilmore was also wounded, and the fourth man surrendered.
Short's body was brought back to Galena for burial.
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