Harvey Bailey found himself at the top of the federal government's most-wanted list in the summer of 1933, quite an accomplishment for a man who began and ended the year in prison.

However, between Memorial Day and September, Bailey would join Wilbur Underhill and nine other convicts on a spectacular escape from the Kansas state penitentiary, abducting the warden along the way, then participate in a few bank robberies and be accused of playing a part in the Kansas City Massacre and the kidnapping of Charles Urschel. He'd get captured while in possession of some of the ransom money, escape a Texas jail all by himself, get recaptured four hours later ... and finally be convicted of the Urschel kidnapping and sent to a federal penitentiary. He was bounced from institution to institution, but remained a prisoner until 1964, and far outlived most of his old pals.

Niagara Falls Gazette, September 14-15, 1933
It’s a far cry from the prosaic life of a farm boy in the quiet hills of northern Missouri to that of “the most dangerous criminal in the nation,” but Harvey Bailey has traveled that road, and now the law has closed in on his career of outlawry, the most spectacular the southwest has known since the days of Jesse James.

Chained to an iron cot in a cell in Oklahoma City’s jail is this super-desperado, kidnapper, jailbreaker, machine gun killer and bank robber who is the prize catch in the federal government’s new war on crime. The 48-year-old Bailey faces trial in federal court there on September 18 for the kidnapping of Charles F. Urschel, Oklahoma oil millionaire, for whose release ransom of $200,000 is said to have been paid.

Uncle Sam, warned by Bailey’s recent single-handed escape from a cell in the Dallas, Texas, jail, is taking no chances this time. Not only is Bailey handcuffed and shackled in such a manner he can hardly move, but guards armed with machine guns surround the jail to prevent any possibility of Bailey’s escape or his rescue by members of his band.

WHAT SORT of man is this Bailey, accused as the “brains” of a huge kidnap ring, even suspected in the Lindbergh case, identified as the ringleader in the biggest bank robbery on record and as a machine gun killer in the Kansas City Union Station massacre of four officers and who was the leader of the daring break of 11 convicts from the Kansas state penitentiary last Memorial Day?

When Harvey Bailey is brought into court at Oklahoma City to answer for the Urschel kidnapping, spectators and jury will see a man far different from the type implied by his reputation as “the most dangerous criminal in the nation,” the description given him by Assistant United States Attorney General Joseph B. Keenan, in charge of the federal government’s war on the underworld.

Instead of a shifty, scowling bandit, Bailey is a big, powerful man with graying hair and a bland smile. Attired in a tuxedo, he could easily fit into any social event and make himself perfectly at home in the role; in golf togs, he would make a good companion for a foursome, for he loves the game and plays it well.

BAILEY'S LIFE STORY is another epic of the country boy who went to the city and made good in a big way — only this country boy turned to crime instead of legitimate pursuits.

Back in Sullivan County, Missouri, Bailey’s parents still till the small farm on which he was born and where he grew up as a big, good-natured boy who always did well in school and made friends with everybody. He left home at an early age to take a fireman’s job on a railroad.

The World War came along and Bailey joined the army and went to the front. That’s where he learned to play the machine gun — and there he met some young recruits from Chicago who were to play a big part in his life later on. With them, he formed some fast friendships.

HOME FROM the war Bailey came, no longer a farmer boy or a young railroad fireman, but a six-foot man weighing more than 200 pounds and well seasoned for whatever the world had to offer.

After a time on the farm, Bailey developed a desire to see some of his war-time buddies. So he bought a one-way ticket for Chicago, and at this point his whole career turned.

In Chicago, Bailey found his former Army acquaintances engaged in underworld pursuits, and through them began his criminal career. He became a liquor runner, smuggling whiskey from Canada by auto, and made money fast. His inherent traits of leadership soon manifested themselves, and he rose rapidly to a position of power among Chicago gangsters.

THOUGH A MEMBER of the underworld, Bailey liked to play the part of a gentleman. His excellent English, which he seldom drops for underworld slang, stood him in good stead when he donned his golf knickers and appeared at some of the most exclusive courses in the city. He liked to live at good hotels and put on all the outer appearances of wealth and refinement.

By 1929, Bailey was deep in the secrets of Chicago’s gang leaders, and in February of that year came the St. Valentine’s Day massacre in which seven gangsters were lined up against a garage wall and mowed down by a machine gun.

A short time after this crime, Bailey returned to his rural Missouri community with a man whom he introduced as “Mr. White.” The latter, Bailey said, was a real estate man “who was seeking a quiet place in the country to recuperate from a nervous breakdown.”

Bailey went back to Chicago and soon thereafter “Mr. White” was identified as Fred Burke, notorious killer and alleged operator of the machine gun in the St. Valentine’s Day massacre. Officers were tipped off by an amateur sleuth who ran a filling station and had recognized Burke from a picture in a detective magazine.

When the officers surprised Burke as he slept in a farm house near Milan, Missouri, they found a machine gun and two automatics at his bedside, ready for instant use.

Later, Burke was convicted of the murder of a St. Joseph, Michigan, policeman, and sentenced to life in prison.

BY THIS TIME Bailey had quit Chicago’s gangs, organized an outlaw band of his own, and turned bank robber on a big scale. In September, 1930, according to witnesses who have since identified him, he was the ringleader in the $2.7 million robbery of the Lincoln National Bank of Lincoln, Nebraska, the largest on record. He also was accused of a string of other bank robberies.

In July, 1931, Bailey was surprised by detectives while playing golf on a Kansas City course and arrested. A short time later he was sentenced to 10 to 30 years in the Kansas penitentiary for the $32,000 robbery of the Citizens Bank at Fort Dodge, Kansas.

The day sentencing, one of Bailey's attorneys, J. Earl Smith, of Tulsa, Oklahoma, was lured to a lonely road by a fake telephone call, beaten and murdered. The crime remains unsolved.

ON MEMORIAL DAY, 1933, Bailey led 10 other desperate convicts in a daring escape from the Kansas penitentiary, kidnapping the warden and two guards, and holding them as hostages until they were released in the Oklahoma hills several days later.

With Bailey at liberty again, things began to happen. There was a string of bank robberies throughout the southwest, then the machine gun murder of four officers at Kansas City when desperadoes attempted to effect the release of a captured pal, and, finally, the daring kidnapping of Urschel from his palatial Oklahoma City home.

If Bailey “beats the rap” at his Oklahoma City trial for kidnapping, he still will have before him the threat of death in the electric chair for his part in the Kansas City Union Station massacre.

Bailey and Albert Bates, alleged lieutenant in his gang of kidnappers and bank robbers, are to be tried in federal court in Oklahoma City on September 18. Of all the crimes charged against Bailey, the Urschel kidnapping and the Kansas City slaughter stand out as among the most daring.

THE EXCITEMENT caused by Bailey’s escape from the Kansas penitentiary, when he kidnapped the warden and led 10 other convicts in a successful dash for liberty, had hardly died down when the nation was shocked on June 17 by the machine gun slaughter in Kansas City. And Bailey, according to federal officials, has been identified as one of the two men who operated the guns that poured their deadly rain of lead into the unsuspecting officers.

It happened this way:

Frank Nash, escaped train robber and alleged member of the Bailey gang, had been captured at Hot Springs, Arkansas, and was being returned to the federal prison at Leavenworth, Kansas.

The officers and their prisoner emerged from Kansas City’s depot and entered an automobile for the drive to Leavenworth. Just as they seated themselves, Nash — either as a signal to the gang that was waiting to rescue him from the law or to show them he was handcuffed — raised his manacled hands above his head*.

Instantly, a roar of machine gun fire burst from a nearby auto containing several men. Four officers and Nash were killed. One of the victims was Raymond J. Caffrey, a special agent for the U. S. Department of Justice, and immediately the federal government stepped into action.

The auto containing the machine gunners dashed away and disappeared, but the government says it has proof Harvey Bailey manned one of the machine guns and gave the order to start firing. Apparently the gang was planning to free Nash before the officers could get him back to the penitentiary.

AFTER THE KANSAS CITY slaughter, Bailey disappeared from the public eye — but not for long.
On the night of July 22, Charles F. Urschel, who had married the rich widow of Tom Slick, “king of the wildcatters” in Oklahoma’s oil fields, was playing bridge with Mrs. Urschel and a couple of friends on the sun porch of his palatial Oklahoma City home.

Without warning, two men armed with machine guns entered.

The strangers forced Urschel to accompany them. The millionaire was placed on the floor in the back of an auto and, while one of the machine gunners sat over him, was driven for hours to a remote farm which, as later events proved, was near Paradise, Texas, 40 miles from Fort Worth.

LOCKED IN a rear room of the farm house and later in a tenant shack on the same farm, Urschel was kept prisoner for nine days. In the meantime, his captors negotiated for his release and a ransom, said to have amounted to $200,000, was paid. The money changed hands in a Kansas City hotel.

Shortly thereafter, Urschel’s captors drove him to the outskirts of Norman, Oklahoma, 20 miles from Oklahoma City, and released him in the road.

Urschel, who had noted that airplanes had passed over the farm regularly at 9:15 a.m. and 5:45 p.m. each day, communicated this fact to authorities. By checking airplane schedules, they ascertained the location of the Texas farm where he had been held captive.

IN THE DARK HOURS of the early morning of August 15, nearly 20 officers advanced upon the farm house of R. G. Shannon near Paradise. With them went Urschel himself, armed with a shotgun.

Asleep on a cot in the farm yard was a large man, a rifle beside him, a machine gun leaning against the porch nearby and two heavy automatic pistols within arm’s reach. The officers approached cautiously, removed the guns, covered the sleeper with their own weapons, and woke him up.

And Harvey Bailey, showing no more resentment than a complaint over his disturbed sleep. roused himself, submitted to the handcuffs and was taken to Fort Worth.
“Okay, fellows, I know when I’m licked,” was Bailey’s smiling comment.

While the actual kidnapping is thought to have been committed by Bates and George “Machine Gun” Kelly, who is still at large, Bailey is regarded by government officers as “the brains” of the gang.

Bates was later captured in Denver and returned to Oklahoma City for trial. Kelly is a son-in-law of Mrs. Shannon, wife of the farm’s owner, having married a daughter born of Mrs. Shannon’s first marriage. Mr. and Mrs. Shannon and their son, Armon, also were arrested. Some of the marked ransom money was found on Bailey.

THE CAPTURE of Bailey was gratifying to the government because it apparently had killed two birds with one stone. Federal agents who had been working day and night to round up the Union Station killers suddenly had thrust upon them the Urschel kidnapping. Now they had Bailey, who was wanted for both jobs.

The desperado’s next sensational escapade came last Labor Day.

From the Dallas, Texas, jail, to which he had been transferred, Bailey made one of the most daring single-handed escapes in history. In some manner, saws and a revolver had been smuggled to him. He sawed his way out of a death cell, locked up three guards at the point of his pistol, kidnapped a turnkey and fled in the latter’s automobile in a wild dash for liberty.

Four hours later, Bailey was captured in Ardmore, Oklahoma, 100 miles away, when his auto crashed into a curb while officers were chasing him. Bailey surrendered without resistance and was taken to Oklahoma City to await trial.

* Frank Nash did not raise his hands over his head as a signal, but as a reflex action when the shooting began. It is believed the men who set out to rescue Nash believed he would be seated between two lawmen in the back seat of the car. Instead, he sat in the passenger seat up front. The two persons in the vehicle who survived were the lawman seated behind the driver and the one seated where Nash was expected to be.

Syracuse Journal, October 7, 1933
OKLAHOMA CITY, Oklahoma (INS) — Four persons, including Harvey J. Bailey, “the most dangerous criminal in America,” and Albert L. Bates, notorious desperado, were sentenced to life imprisonment today by Federal Judge Edgar S. Vaught for the $200,000 kidnapping of Charles F. Urschel, oil millionaire.

Mr. and Mrs. R. G.. “Boss” Shannon of Paradise, Texas, on whose farm Urschel was held prisoner, were the other two given life sentences.

Their 22-year-old son, Armon Shannon, was given a sentence of 10 years in the federal penitentiary, but Judge Vaught suspended sentence and will allow him his liberty on probation. Armon helped his father guard Urschel.

Edward “Barney” Berman and Clifford Skelly, the St. Paul defendants accused of having passed $5,000 of the $200,000 ransom money, were both sentenced to five years in the federal penitentiary.

Thus the United States government wrote a smashing finale to the lurid careers of the most menacing ring of kidnappers, killers and desperadoes to infest the Southwest since the days of Jesse James.

It was the government’s master stroke in its first prosecution under the federal kidnapping act — the law “with teeth in it” passed by Congress after the abduction of the Lindbergh baby.

George “Machine Gun” Kelly and his wife, Kathryn, will go to trial on the Urschel kidnapping charges before Judge Vaught Monday morning.

The Kellys sprang a surprise this morning by changing their minds and pleading “not guilty.” They had come to court with the government confidently believing they would plead “guilty.”


Syracuse Journal, October 9, 1933
LEAVENWORTH, Kansas (INS) — Anonymous federal prison numbers today designated two of America’s most-feared desperadoes, Harvey J. Bailey and Albert Bates.

The two gunmen were hurried here by airplane to begin serving life sentences for the $200,000 ransom kidnapping of Charles F. Urschel, millionaire Oklahoma oil operator.

They were convicted in the first test of the new federal “Lindbergh law” aimed at interstate kidnapping.
The two desperadoes were locked in receiving cells for three days of observation before being assigned to regular places in the penitentiary.

Ten heavily armed federal officers accompanied the pair here from Oklahoma City in a tri-motored plane.

Bailey’s only comment before the prison doors clanged shut behind him was, “The walls look pretty high for me to get over.”

Bailey led a break from the Kansas penitentiary, just eight miles from here, in which 11 convicts escaped last Memorial Day. On Labor Day, he fled from the Dallas County jail. Bates escaped from the jail at Paw Paw, Michigan.

Bailey was transferred to Alcatraz a year later, then returned to Leavenworth in 1946, and transferred again in 1960 this time to Seagoville Federal Correctional Institution in Texas. Though given a life sentence, Bailey was released from prison in 1964 when he was 77 years old.

He settled in Joplin, Missouri, which seemed to be a popular place for gangsters from his era. In 1966 he married Esther Farmer, who had served them for her participation in the conspiracy to free Frank Nash from the custody of federal agents. That led to the so-called Kansas City Massacre at the city's Union Station. Her husband, Herbert "Deafy" Farmer also was sent to prison.

The Farmers were reunited after they completed relatively short prison sentences and they moved to Joplin, where he died in 1948. She was 78 when she married Bailey, he was a year older.

Bailey died in Joplin in 1979, at the age of 91. She died two years later. The Baileys are buried together in Forest Park Cemetery, Joplin, not far from her first husband.