In a letter to August Derleth, dated September 4, 1933, Howard writes about his attempt to get a look at a jailed notorious bank robber and associate of George “Machine Gun” Kelly while on a trip to Dallas:
Speaking of outlaws, I hear that Harvey Bailey, the machine-gun bandit was captured in Ardmore, Okla. It was only this morning that he escaped from the Dallas county jail. I was sure that he’d head for Oklahoma. On one of my trips to Dallas a friend of mine was much desirous of getting a peek at the notorious criminal, and tried to find the Federal attorney (a friend of his) who was prosecuting Bailey, thinking he’d let us see the fellow, but without success. The jail seemed well guarded, but somehow Bailey did manage to slip through. Bailey had been captured in a farm-house not far from Decatur, in Wise County.
This letter was written on September 4, which was Labor Day, and the day of Harvey Bailey’s escape from the “escape-proof” Dallas County skyscraper jail. Bailey bribed a jailer, Thomas L. Manion to smuggle him a pistol and two saws. Manion and Bailey then took turns sawing through the bars and soon an armed Bailey was on the loose with a hostage, jailer Nick Tresp. But his freedom was short-lived as Bailey was recaptured the same day in Ardmore, Oklahoma. Manion and a civilian, Grover C. Bevill, who had furnished the hacksaws, were later convicted of aiding Bailey’s escape and sentenced to two years and fourteen months, respectively. But Bailey had his own version of the escape: he would claim in later years that Manion brought him the gun and saws of his own accord, likely plotting to shoot Bailey during the jail break and claim a reward. There was some truth to this — Manion wanted to run for sheriff — and when Bailey and his hostage left in the getaway car, he spotted Manion and Bevill waiting in ambush, so he headed in the opposite direction.
John Harvey Bailey was one of the most successful bank robbers of the Depression Era. He worked in a gang or alone, and his career spanned 13 years and several states. Bailey actually stole more money than John Dillinger, but is less well known. In 1931, his gang robbed the Lincoln National Bank in Lincoln, Nebraska and escaped with an estimated $1 million in cash. Following the heist, he is said to have hidden the loot on a farm near Richmond, Illinois, where he had been hiding out. He robbed his last bank in Kingfisher, Oklahoma and was sentenced to life in prison on October 7, 1933. He served his time and was released in 1965. He died fourteen years later at the age of 91, apparently without recovering his stash. To this day, no one knows what happened to the $1 million.
Bailey was born in West Virginia, on August 23, 1887; he grew up on a farm in Sullivan County, Missouri and worked as a fireman on the railroad before joining the Army during World War I. After the war, he settled in Chicago where several of his Army buddies lived. Those friends were into some highly illegal endeavors and soon were enticing him into the fold. It was the early days of Prohibition and former soldiers were in great demand to provide muscle to the underworld gang known as the Chicago Outfit, led by John Torrio and an up and coming Al Capone. Bailey decided to join them and was soon knee deep in the liquor smuggling business, driving fast cars loaded down with whiskey from Canada to Chicago.
Bailey robbed his first bank in 1920 and in December of 1922 is believed to have robbed the Denver Mint of $200,000. Altogether, he robbed some twenty banks. He meticulously planned his bank jobs, obtaining road maps from the county surveyor to learn his getaway routes and was thought to have been involved in two infamous gangland shootings — the St. Valentine’s Days Massacre in Chicago and the Kansas City Union Station Massacre. However, there was never any concrete evidence placing him at either scene. Bailey was also one of the last outlaws to join the Ma Barker gang and he threw cold water on the legend of the old gal as a criminal mastermind when he told author L.L. Edge for his book Run the Cat Roads the following:
“The old woman couldn’t plan breakfast. When we’d sit down to plan a bank job, she’d go in the other room and listen to Amos and Andy or hillbilly music on the radio.” Bailey found laughable the idea that the Barkers, Alvin Karpis, Frank Nash and other professionals would depend on Ma Barker to plan their crimes. She may have been overly indulgent, protective and possessive of her sons, and would harbor their friends from the law; in return they treated her regally, kept her in fancy clothes and cars, without her questioning the source of their prosperity. However, the image of Ma Barker as a cunning, ruthless gang leader appears to be as exaggerated as the largely mythical exploits of Belle Starr, to whom she has often been compared.
It was tough to keep Bailey behind bars. He was incarcerated in the Kansas State Prison on July 8, 1932 and escaped on June 1, 1933 during a breakout in which the warden and two guards were kidnapped and used as human shields. On August 12, 1933 he was recaptured near Paradise, Texas and locked up in the Dallas county jail, but escaped as detailed above on September 4, 1933.
Following his June 1, 1933 escape, Bailey hooked up with George “Machine Gun” Kelly. Police, while searching for Kelly for the kidnapping of Oklahoma oil tycoon Charles Urschel, descended on the Paradise, Texas farm belonging to the family of Kelly’s wife, where Bailey was sleeping. The lawmen assumed Bailey was small fry, but found $500 of the Urschel ransom money and realized they had captured “Old Harv.”
Soon after he was recaptured after the September 4, 1933 Dallas jailbreak, he was found guilty of complicity in the Urschel kidnapping and sentenced to life in prison on October 7, 1933. As it turned out “Old Harv” had nothing to do with the Urschel kidnapping – he was in the wrong place at the wrong time. The cash Bailey had from the ransom money, it seems, was repayment of a debt from Kelly — Bailey did not know its origin. Nonetheless, it was a high profile crime and J. Edgar Hoover wanted justice done and he got it, although misplaced in Bailey’s case. Bailey was sentenced under the new Federal kidnapping laws that had a mandatory sentence of life in prison. While he was guilty of laundry list of crimes, he was innocent of the kidnapping charges.
Bailey was originally sent to Leavenworth, then he was transferred to Alcatraz on September 1, 1934. He was returned to Leavenworth in 1946 and transferred in 1960 to Seagoville Federal Correctional Institution in Texas, where he remained until 1962 when he was sent to the Kansas State Penitentiary to serve time for his escape from there in 1933. He was finally released on March 31, 1965.
Once Harvey was released, E. E. Kirkpatrick, who had delivered the Urschel ransom money, and Urschel himself tried to make things right by providing financial support for Bailey. In fact, while he was still in prison, Kirkpatrick had tried to help Bailey with his unsuccessful parole request in 1958, writing:
Bailey had nothing to do with the Urschel kidnapping … We all know that. He was unlucky enough to be hiding at the Shannon farm.
In October of 1966, after a year-long courtship, Bailey married Esther Farmer, the widow of Herbert Allen “Deafy” Farmer, whose family operated a well-known safe house in southwest Missouri for all the outlaw gangs that roamed the Midwest during the 1920s and 1930s. “Deafy” Farmer was also one of the Kansas City Massacre conspirators and close confidant of the Barker Gang, particularly Fred Barker.
In 1973 author J. Evetts Haley wrote a biography of Hailey titled: Robbing Banks Was My Business…the Story of J. Harvey Bailey (Palo Duro Press, Canyon, Texas). Bailey was interviewed extensively and provided a wealth of information, even though his memory was spotty in places. The book is nearly as rare as Jenkins’ A Gent from Bear Creek, with autographed copies in fine condition going for in excess of $1,000. In fact, only seven libraries in the country have a copy for circulation.
Bailey died on March 1, 1979 in Joplin, Missouri and his wife passed away in 1981. Both are buried in the same grave at Forest Park Cemetery in Joplin.