This is the second in a series of posts about David T. Hardy’s research on Jack Miller, the defendant-respondent in the famous case of United States v. Miller, 307 U.S. 174 (1939). The first post is available here.
Popular lore has it that Jackson “Jack Miller” was the Native American member of the O’Malley Gang, a mostly Irish band of bank robbers. This tale is only partially true.
For starters, Miller was indeed Cherokee, whose family had traveled the “Trail of Tears” to Oklahoma. Jack’s father, James Miller, had been a medicine man to the Cherokee, so well-regarded as to draw patients from several states. Jack’s great-grandfather, Jack “Squan” Miller, had born in Georgia and walked the Trail of Tears to Oklahoma. In Oklahoma, he built an inn; family lore has it that Sam Houston (who spent years living with the Cherokee, spoke their language, and was adopted into their nation) was a frequent guest.
But if Jack Miller was indeed Cherokee, the O’Malley Gang was not very Irish. It was a group of robbers, named for its leader’s alias – he was Walter Holland, a/k/a Leo “Irish” O’Malley. Some contend that it had evolved out of, or perhaps absorbed, a gang known as the “Ozark Mountain Boys.” By 1935, it was one of the last, if not the last, of the great bank robbery gangs. John Dillinger, Pretty Boy Floyd and Bonnie and Clyde had all been killed the previous year; Ma Barker was killed and her gang were captured in January 1935. Thereafter, the gang was virtually the only survivor: a newspaper article related that “G-men credit the gang with most of the major bank robberies in the southwest over a period of two years….”
Miller’s association with the gang was brief and likely driven by desperation. He’d had a prosperous business, and the sheriff, Bill Flippin, pressured him to pay protection money. (If that seems a strange activity for a law enforcement official, Flippin was decidedly dirty. He would ultimately be charged with everything from bootlegging to riot and murder, and serve time in prison). Miller refused to pay, and one night his business burned to the ground. One of Flippin’s squad cars was seen parked in the area shortly before the fire.
(As you might gather, the situation in dustbowl-era Oklahoma might be classed as “morally ambiguous,” much like the Old West. The line between lawmen and criminals was a fine one, with many people crossing back and forth at will).
Miller became associated with the O’Malley gang while he and they were in Kansas City. He wrote home to his family that they’d offered him a job and, while they had been bank robbers, his family need not worry since the gang had retired from that field and settled down to ordinary business. That wasn’t the case.
The O’Malley gang was very loosely knit, with members coming and going, and joining or not in particular heists. At the time of the bank robbery in which Jack Miller was involved, those taking part were Holland, “Dapper Dan” Heady, Leonard Short (the brother of congressman Dewey Short (1934-1956)), Russell Cooper, Fred Reece, Virgil Melton, and Dewey Gilmore, described by a newspaper as a “hulking, mustached Missouri police character.”
The robbery was to be an ambitious one, a double robbery, hitting the Okemah National Bank and the First National Bank in Okemah, Oklahoma. A double robbery would be very profitable (in fact it netted $41,000, about $940,000 in modern money). On the other hand, it would be complicated and risky (the Dalton Gang tried one in Coffeyville Kansas, with disastrous results, and Henry Starr and his gang tried one at Stroud, Oklahoma in 1915, which ended with Starr shot out of the saddle by a young boy wielding a .22 rifle).
Unlike those gangs, the O’Malley Gang had automobiles, which conferred a great advantage in the days before police cars had radios. (Congressional hearings which led up to the 1934 National Firearms Act dealt at length, not only with guns, but with automobiles. Police communications, where they existed, consisted of telephones in special boxes on the street. Bank robbers could be out of town and many miles down the road before the first squad car got the alert).
What we know of the Okemah heist comes from newspaper coverage of the trial of the gang, in which Miller turned state’s evidence and gave testimony that was at the heart of the prosecution’s case. The trial was a tense affair, with federal agents fearing an attempt at rescue: a newspaper described the courtroom as “bristling with machine guns and high-powered rifles.” Miller, the article added, had been held at the state penitentiary, likely for his own protection.
Miller’s testimony was detailed. What was his involvement with the O’Malley boys? Miller testified that Heady approached him and asked him to serve in a “follow up” role. The O’Malley gang liked to ditch their getaway car and substitute another while fleeing a robbery, and so Miller would be waiting with the substitute car outside of town. He would be compensated for his role with a share of the loot.
But, Miller testified, he didn’t really want to be involved in the robbery. He told Dewey Gilmore of this, and they agreed that Miller would evade his part in the flight, and Gilmore would tell the others that Miller had fallen asleep while waiting for their arrival. In return, Miller would give Gilmore Miller’s share of the loot.
The plan worked, and according to newspaper reports, the gang sped past Miller’s position without changing cars.
Miller’s testimony on his role shocked the gang members. A newspaper reported that as he testified the other gang members shot up in their seats and Short mouthed the words “did you really do this?” to which Gilmore nodded yes.
The U.S. Attorney trying the case had announced at the beginning that Miller had been given immunity for his testimony, and at the end of the case Judge Heartsill Ragon (yes, the same judge who would later hear the NFA case against Miller) instructed the jury to acquit him. (Yes, in those days an “instructed verdict” was literally that).
The rest of the gang did not get off so easily. Melton and Reece pled out, and the rest were convicted. The gang’s story, however, does not end here.
The gang was held in the Muskogee jail pending sentencing. During their incarceration, Gilmore’s wife, “Pretty Betty,” managed to pass him a gun. He and three other gang members shot their way out of the Muskogee jail, killing detective Ben Bolton and a prisoner. An enormous manhunt (involving law enforcement, a company of National Guard, and a posse) tracked the escapees; of the four, Heady and Short were cornered and killed (reports disagree on whether Short was shot, or burned in a cabin fire, or died of exposure and pneumonia), while Gilmore and Cooper were recaptured and given life sentences for the murder.
The gang had one last impact on Jack Miller’s life. A newspaper reported, “When news of the jail break came, Miller was at Muskogee collecting his witness fee. He applied to District Attorney Summers for protection and was kept in jail until the gang was recaptured.”
