Harvey Bailey

Fame, they say, is fleeting. And that's certainly true for Harvey Bailey, once one of the most famous men in the United States and today virtually unknown.

Except for crime buffs, of course. Yes, in the 1920's and 1930's Harvey Bailey was one of the nation's most famous criminals.

Harvey got involved in crime almost by chance. He served in the Army in World War I and some of his army buddies hailed from Chicago. So after he got out he went to the Windy City to look them up and found they were involved in, well, less than reputable enterprise.

That was in the early 1920's and just when Al Capone who at the behest of Johnny Torrio had moved from New York to Chicago. Starting in 1919 it was illegal to manufacture, sell, or transport alcoholic beverages. But Johnny and Al found you could make big bucks doing just that.

Bootlegging wasn't the only crime around, but it did help solidify the concept of the celebrity gangster. The problem with bootlegging was to make real money you had to be part of a well-established gang with enough muscle to keep rival mobs out of your territory. Doing so effectively could be hazardous to your health as Johnny Torrio found out.

One job in a well oiled bootlegging enterprise was to be a "rum runner". You'd load up your car with booze at the distillery or brewery and deliver it where needed. That could be a central warehouse or a local bar. A good rum runner knew the back roads to all the major cities.

The best source of liquor was Canada. A runner would drive to and from Canada - Windsor, Ontairo is just east of Detroit - and unload top-notch hooch where the gang wanted it. Harvey found this business plan was particularly lucrative.

But a rum runner had to be tied to a particular gang. If he (and most of them were men) tried to go independent he found his customers dried up. He wouldn't dry up, though, because he would find himself at the bottom of Lake Michigan.

Looking for independent ways to make a big buck, Harvey decided to switch to bank robbing. This was an endeavor that could be handled by single entrepreneurs with perhaps one or two partners.

Harvey has been credited with almost 30 bank robberies from 1920 to 1932. Supposedly he never pulled a job without making detailed plans and perhaps for this reason no one was ever seriously hurt during his heists. He was credited with being the brains behind a robbery on September, 1930 at the Lincoln National Bank in Lincoln, Nebraska, that pulled in over $2,000,000.

Harvey's business was booming, and in June 1932, he robbed a bank in Fort Scott, Kansas. Then a month later while relaxing with a nice game of golf on a Kansas City links, he was arrested and sentenced to 30 years at the Kansas State Penitentiary at Lansing.

Like most prisons there was time set aside for recreation. After all, all prison industries and no play makes Harvey a mean inmate. Baseball was particularly popular and usually the warden would stop by to watch.

Then on June 1, 1933, while a game was underway, one of the convicts - early stories say it was the convicted murderer Wilbur Underhill - threw a wire around the warden's neck and someone else - we read it was Harvey - pressed a gun to his back. They tersely informed the warden that they were going to kill him unless they got free.

Although there were armed guards on the walls, the warden told them to put their guns down and not to shoot. The gang of convicts - ultimately they numbered eleven - went to the door of a guard tower and then to the outside of the prison. There they commandeered the car of the prison farm superintendent and headed south. The warden was finally released near Welch, Oklahoma, a town 70 miles northeast of Tulsa.

This wasn't really the time to make a jail break where you threatened the warden with death. Particularly a jail break not far from Kansas City . Harvey soon became one of the prime suspects in what is called the Kansas City Massacre.

On June 17, 1933, a group of gangsters ambushed a group of law officers at Kansas City's Union Station while the officers were taking a prisoner, Frank Nash, to Leavenworth. Four officers were killed and one was a federal agent. Although the only real consensus is that the Massacre was organized by a former sheriff turned gangster named Verne Miller, Harvey was an immediate suspect. Things were really hot for him now and he needed to get far away and find some funds.

Harvey headed to Texas to the farm owned by Charles "Boss" Shannon and his wife Ora. They had one daughter, Kathryn, who had married a man from Memphis named George Barnes. However, Kathryn and George were married under the name Kelly, and "Machine Gun Kelly" had been in the news particularly since he had kidnapped the Oklahoma oil magnate Charles Urschel. While waiting for the $200,000 ransom, Machine Gun kept Charles on ice at the Shannon ranch.

But the Shannon ranch was also known as a "safe house", a place where fugitives could stop and hide out for a while. Also George owed Harvey some money, and he figured Boss would help square him.

Although Charles had been blindfolded, he had been able to remember non-visual events that helped the agents pinpoint the Shannon's farm. But for now Boss, Ora, and Harvey were blissfully ignorant of this fact.

When Harvey showed up, Boss handed over a few hundred of the ransom money and suggested Harvey get some sleep on a cot outside the house. That was the custom during the summer on the Texas plains in those non-air-conditioned days. Harvey was happy to catch forty winks.

But he wasn't so happy when he woke up the next morning staring at a ring of gun barrels each backed by a federal agent. He surrendered without a struggle.

Bad luck, Harvey. He was not only going to be pinned with his escape from the penitentiary - typically an extra five years added to his original sentence - but with some of the Urschel ransom money in his pocket, now he was going to be accused of the kidnapping to boot!

Never a man to lament a sad situation, Harvey went along willingly to the Dallas jail. But as you may figure by now, Harvey was what prison officials call an escape risk. There and with the help of an unusually oblidging deputy sheriff he managed yet another spectacular getaway. But the end was rather anticlimactic since he was recaptured a few hours later near the town of Ardmore just north the Texas-Oklahoma border.

Even though Boss stated that Harvey was innocent, he was convicted along with Boss and Ora as participants in the Urschel kidnapping, Well, Harvey, you are known by the company you keep. All received life sentences, as in a few weeks so would George and Kathryn.

Harvey began serving his sentence at Leavenworth, but given his reputation and that he was a significant escape risk, he was soon transferred to Alcatraz. He remained on the Rock from 1934 to 1946 before going back to Leavenworth. Then in 1960 he was transferred to the minimum security prison at Seagoville, Texas, just outside of Dallas. Four years later he was released.

Today you'll read that Harvey was one of the most successful bank robbers in America. That may be but he also spent a total of thirty years in jail and didn't get out until he was 78 years old. If that's success, failure looks pretty good.

Harvey had his life written up by the Texas historian J. Evetts Haley, who penned works about other characters like lawman Jeff Milton, rancher and Texas pioneer Charles Goodnight, and someone named Lyndon Johnson (who Evetts didn't like). The book about Harvey, Robbing Banks Was My Business, though, is out of print and used copies are horribly expensive.

Two years after his release from prison, Harvey married Mary Farmer, whose first husband Herbert "Deafy" Farmer, was convicted of complicity in the Kansas City Massacre. Deafy served two years for conspiracy which was all the federal laws could nail him for. For his part, Harvey found honest employment as a woodworker at a cabinet company and lived a law abiding life that lasted until 1979 when he was 91 years old.

References and Further Reading

"Outlaw #1 was Farm Boy: Harvey Bailey, Bandit, Killer, Walked Crime's Road", Robert Talley, The Indianapolis Times, September 21, 1933.

More Oklahoma Renegades, Ken Butler, Pelican, 2006.

"Bandit Underhill Is Shot and Seized", Associated Press, The New York Times, December 31, 1933.

Alcatraz: The Gangster Years, David A. Ward, University of California Press, 2009.

Notorious Kansas Bank Heists: Gunslingers to Gangsters, Rod Beemer, Arcadia, 2015.

"Bailey Recaptured After Daring Break From Jail in Texas", Washington Evening Star, September 4, 1933, Chronicling America, Library of Congress.

"Harvey Bailey", Find-A-Grave, April 16, 2002.