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If asked to identify Harvey Bailey, most folks might guess that was the name of George Bailey's brother in "It's a Wonderful Life."

Close, but no. George Bailey was the name of James Stewart's character; Todd Karns played his brother, Harry, probably born Harold or Henry, but not Harvey. (Stewart also starred in a film called "Harvey," but the title character was an invisible six-foot rabbit with no last name.)

Thus ends my silly introduction to a long story about a bank robber named Harvey Bailey, who, in 1933, was briefly atop the federal government's most-wanted list, quite an accomplishment for a man who began and ended the year in prison, and spent most of his life overshadowed by other criminals. And while you'll find online a description of Bailey as the greatest bank robber of all-time, keep in mind that until 1932 — after he'd been in the hold-up business for 12 years — the man could have been a member of Outlaws Anonymous. In fact, when he robbed his first bank, his associates knew him by his alias — Tom Brennan. It wasn't until he was 45 years old — a senior citizen by bank robber standards — that Harvey Bailey became publicly known by his real name. That came about after one of the more unusual arrests in the history of what would soon become known as the Federal Bureau of Investigation. (More on that later.) After agents uncovered the real name of the man they'd inadvertently apprehended, Bailey went from being regarded as a nobody to a very desperate and dangerous criminal.

With that came unwanted notoriety fanned by his association with previously better known outlaws and by three assumptions that eventually proved to have no basis in fact, though one resulted in an arrest, a guilty verdict and a life sentence that hastened his return to obscurity. The guilty verdict, for a kidnapping, was an injustice, because Bailey was not involved in the abduction, but he happened to know those who were, and had the bad luck to drop in at a "safe house" used by the kidnappers. Bailey, who'd escaped prison months earlier, was nursing a bullet wound and needed a place to rest, but his visit was ill-timed, and he was arrested by lawmen who were looking for someone else. It wasn't the first time Bailey was in the wrong place at the wrong time.

However, after his conviction for involvement in the kidnapping of Oklahoma oilman Charles F. Urschel, no tears were shed for Bailey; he deserved to be behind bars, and being there probably is why he outlived almost all of the other outlaws of his era.

Today he is forgotten, but in 1933, he could have been named the outlaw of the year. I became aware of Harvey Bailey only because, like federal agents in the 1930s, I came upon him while looking for material about more famous outlaws, such as John Dillinger, Wilbur Underhill and George "Machine Gun" Kelly. Bailey had several things in common with these and other outlaws of his era, but, overall, he was a much different person and led what I think was a more interesting life than most, though details of that life are hard to come by.

A WORD of caution to anyone who keeps reading. Much that has been written about outlaws who enjoyed a measure of fame throughout our history is bogus or highly suspect. Because he managed to remain invisible to police and the press for so long, Harvey Bailey seemed to arrive out of nowhere when he was in his mid-40s. That he hadn't attracted attention sooner is surprising because he was involved in some notable bank robberies over the years. And he was a distinctive-looking person, once described as "a man of massive stature." Since most of those robberies were committed while making no attempt to cover his face, you'd think witnesses would have commented more about the hulk who seemed to be in charge of the heist.

Part of the problem, of course, is Bailey/Brennan, like most robbers, selected banks in small cities or even smaller towns, where getaways were made quickly over lightly traveled roads. These places often had inexperienced, even incompetent police departments. There also was a lack of communication between police departments, and a tendency to attribute robberies to a familiar name. Since some regarded Depression-era bank robbers as heroes of a sort, victims, as well as other citizens of the town, preferred to say they were robbed by "Baby Face" Nelson than by some young nobody. It was a status thing.

To say Harvey Bailey was a man of "massive stature" is an exaggeration. He stood at least six-feet — which was large for his era — and his tuft of hair made him look two or three inches taller. He weighed about 200 pounds. He was described as looking more like a bank president than a bank robber, but photos of him put me in mind of a high school math teacher who has disdain for students who can't grasp geometry.

He was different from other outlaws in other ways. For one thing, he was at least 10 years older then most of them, and, considering his line of work, his career lasted a lot longer than average. Once he became known to federal agents, however, his bank-robbing days were numbered, and his reputation became much worse than he deserved because his name suddenly was connected with terrible crimes he didn't commit. He was described as a killer, though that was true only in a strictly legal sense. That is, at least one man was killed by a gang member in a Bailey-led robbery, but there is no proof Bailey himself ever shot anyone.

His luck, incredibly good until 1932, turned against him in strange, almost amusing ways. Bailey certainly didn't find it funny, but accepted his bad luck rather philosophically. One suspects he wanted to lead a law-abiding life, and, indeed, he gave it a try more than once, but circumstances provided an excuse to look for a quick payoff.

SOURCES disagree whether he was born John Harvey Bailey or Harvey John Bailey, but agree his birth took place in West Virginia in 1887. In any event, he chose to use Harvey as his first name, but in his early 30s, he went on the run from the law in Iowa and settled in North Dakota as Tom Brennan.

Bailey's family moved from West Virginia to Sullivan County, Missouri, in 1900. His father, a Union captain during Civil War, ran a farm. His son, Harvey, left the farm in 1905 and took a job as a railroad fireman. Most sources say he joined — or was drafted into — the Army and fought during World War One. Some stories claim it was in the Army that Bailey learned to use a machine gun, and that he got into bootlegging after the war when he looked up some Army buddies who lived in Chicago.

Something about the Army story never seemed right to me. Bailey was 29 years old when the United States entered the war, and unlikely to be drafted. My suspicions were confirmed when I came upon an Associated Press story from September 21, 1933, published while Bailey was on trial in connection with the kidnapping of Charles F. Urschel.

“He never planned the Urschel kidnapping. He couldn’t have done the things they charge him with," said Amanda E. Bailey, the outlaw's mother, who'd been a widow since 1921. "A better boy never was born. He never sassed his parents. He comes from the finest families of West Virginia ... None of my boys served in the World War. Harvey never learned machine-gunning as a soldier.”

Certainly a mother would know if her son had been in the Army. Then I found out that by the time the United States entered World War One in 1917, Bailey was married and had two sons.

Fortunately, an online search led to "George 'Machine Gun' Kelly: His Life and Impact," a book-length piece by Marilyn Horton Taylor, who, I believe, is a teacher in Memphis, Tennessee. Along with a biography of "Machine Gun" Kelly, she provided the first believable account of Harvey Bailey's life, something I assume she found by being one of the few people to read an obscure book called "Robbing Banks Was My Business: The Story of J. Harvey Bailey," by J. Evetts Haley, who wrote it in cooperation with Bailey after the outlaw was released from prison in 1964.

BAILEY'S birthdate was August 23, 1887, and his West Virginia birthplace was Jane Lew, a town named for the mother of its first settler. When Bailey was born, the town's population was about 200. Since 1887, Jane Lew has pretty much resisted growth, and today numbers only about 400 residents.

Sullivan County, Missouri, was just as sparsely populated as the area around Jane Lew, West Virginia, but the farm land was better. Not that Harvey Bailey had any intention of staying there.  I haven't found the name of the railroad that hired him in 1905, but an Associated Press story in the Troy (NY) Times on September 5, 1933, said Bailey worked 15 years in Iowa on a train that ran from Council Bluffs to Fort Dodge, a distance of about 160 miles. According to the 1910 United States census, Harvey Bailey lived in Fort Dodge with his wife, Mattie, whom he married in 1907.

Ms. Taylor's story says Bailey was elevated to engineer during World War One, when he made good money. But when the war ended, returning veterans included railroad engineers who reclaimed their jobs, and Bailey was relegated to substitute engineer, which meant less work. He needed a second job, and wasted little time finding one, maybe two.

ANOTHER mistake you'll find in most stories about Bailey is the explanation of how he got into bootlegging. It didn't happen in Chicago, and since he hadn't been in the Army, he didn't follow any war buddies into a life of crime. Bailey did that all by himself. That's because some states were dry before Prohibition went nationwide. Two of those states were Iowa and Nebraska.

That's why, in 1919, Harvey Bailey became a bootlegger in Iowa, and he had plenty of experience smuggling liquor before there was a demand for it in, say, Chicago.

"Once the nation went dry," wrote Ms. Taylor, "Bailey moved his operation to Minot, North Dakota."

I don't believe that's quite accurate. Bailey left Iowa and changed his name for another reason. In addition to bootlegging in Iowa, he'd also become a safe-cracker, and been caught. That September 5, 1933 Associated Press story, in which Detective Inspector A. C. Anderson of Omaha recalls Bailey's time on the railroad in Iowa, has Anderson saying it came to an end after Bailey was arrested for having safe-cracking tools in his possession.

Anderson said Bailey jumped bond, and disappeared. After that, Anderson heard nothing more about Bailey until twelve years later when he was arrested in Kansas City. The detective inspector said he thought Bailey was "a sort of hick," and didn't think he seemed very tough.

By 1933, Bailey was known to police, and was under suspicion for all sorts of crimes. For example, he was mentioned as one of the machine-gun killers at Chicago's St. Valentine's Day Massacre in 1929. That's what prompted Detective Anderson to comment on Bailey's toughness. In truth, Bailey was nowhere near that North Clark Street garage in Chicago on February 14, 1929 when seven Chicago mobsters were gunned down, but he knew Fred Burke, who was indicted — but never tried — for being the massacre's top gun.

IT WASN'T long after he re-located to Minot that Bailey/Brennan robbed his first bank. Again, thanks to Ms. Taylor for providing information about the target, a bank in northwestern North Dakota. Working with two others, Bailey pocketed $5,000, and decided this was a better-paying job than bootlegging, though it was something he didn't intend to do more than two or three times a year.

So he continued to smuggle booze over the Canadian border, and his destinations included St. Paul, Minneapolis and Omaha. It probably was with some acquaintances in St. Paul that Bailey planned and executed what may have been his best heist. At the time, St. Paul was considered a haven for outlaws, who were safe in that city so long as they committed their crimes elsewhere and paid St. Paul police for protection.

The go-between for outlaws and police was Daniel Hogan, nicknamed "Dapper Dan." So after Bailey and three or five other men — the number varies with the source of information — held up a Federal Reserve Bank delivery truck in front of the Denver Mint in December, 1922, Bailey laundered his take through Hogan.

Ms. Taylor's piece says Bailey received 35 to 40 cents on the dollar for security bonds and 85 to 90 cents for Liberty Bonds, which may have been Hogan's usual rates, but no bonds were involved in the Denver hold-up, which was a robber's dream — $200,000 in cash, all of it in five-dollar bills. That's 40,000 five-dollar bills, which were being transferred from the mint to the truck in 50 sacks, each containing $4,000. It was during this robbery that one of Bailey's cohorts shot and killed Charles Linton, a Federal Reserve Bank guard.

The only reasons I can think of for Bailey to hand Hogan $80,000 was for the go-beween to exchange new five-dollar bills for old bills of various denominations, and to pay what was due the St. Paul police department. Why Bailey's take was so much more than other members of his gang — who likely received from $24,000 to $40,000, depending on their number — was because it was his idea and his plan.

The Denver Mint job helped finance Bailey's move to a Chicago subdivision a few months later. He and a man named W. R. Williams bought two Standard Oil service stations, adding the recently invented conveyor car wash systems. According to Ms. Taylor, Bailey also invested in real estate and the stock market, which, in the early 1920s, seemed like a smart thing to do.

WHILE he may have made money from selling gasoline and washing cars, Bailey wanted more, and after lying low for three years, he resumed robbing banks. Along the way, he sold his service stations, but continued to invest some of his money, which he lost in the stock market crash of October, 1929. But by then he was robbing banks again. Ms. Taylor's list of Bailey's robberies includes banks in LaPorte, Indiana ($140,000); Rochester, Minnesota ($30,000); Lacrosse, Wisconsin ($70,000); Washington Court House, Ohio ($225,000); Washington, Iowa ($55,000), and Sturgis, Michigan ($80,000).

Those figures in parenthesis are misleading. For example, the robbery at Peoples and Drovers Bank in Washington Court House, Ohio, on February 6, 1928, netted $23,000 in cash, the rest in securities that would be handled by a middle man. How much Bailey pocketed, nobody knows for sure, but even if it were less than $10,000, that put him ahead of most Americans, whose annual earnings were in the $3,000 to $5,000 range. Also keep in mind how much further money went in those days.

It is estimated that in his career, Bailey stole between one and two million dollars, though I have no idea how anyone arrived at either figure. I'll soon mention a 1930 bank robbery which, for years, was listed as the biggest in United States history, and supposedly it was another Bailey job. If so, it would have run Bailey's total well over four million dollars, unless these guesses regarding his robberies simply estimate Bailey's portion of the take, or the amount of hard cash involved.

By comparison, John Dillinger's 13 bank robberies netted an amount estimated at $300,000 to $500,000. The seven bank robberies attributed to Bonnie Parker and Clyde Barrow netted only about $12,000, not surprising when you consider the small, shaky banks they hit. It's no wonder they usually slept in cars and not hotels.

Ironically, today's lists of notorious bank robbers often have Bonnie Parker among the top five. That just shows what a movie will do for your reputation. By any sensible standard, Bonnie and Clyde (Barrow) were bush league bank robbers, and Ms. Parker herself usually remained in the getaway car.

ONE THING seems true — people in Bailey's line of business got around. While police had no idea at the time who pulled the robbery outside the Denver Mint, they were quick to suspect the job was the work of a Chicago gang later blamed for a similar robbery in Toronto. In 1933, police in Lee, Massachusetts, were alerted to be on the look-out for "Pretty Boy" Floyd from Oklahoma. That was a false alarm, but Floyd did travel as far as Buffalo, New York, where he hid for several months.

Journalists writing about outlaws in the 1920s and '30s often did so in the same spirit as those who wrote about bandits in the Wild West, and almost every bank robber during the Depression was compared with Jesse James. The stories were very much the same; only the names of the robbers were changed.

Which gets me to the 1930 robbery of the National Bank and Trust Company of Lincoln Nebraska, another crime attributed to Bailey. Yes, the robbers escaped with securities said to be worth $2.8 million. Yes, the robbery ruined the bank, but, no, it didn't do the robbers much good, except give them bragging rights ... so long as no one asked how much money they received for their trouble.

Very little loose cash was taken, and that was mostly in coins. Three of the six robbers were soon located, tried, and sent to prison. Meanwhile, it was up to Chicago mobster Gus Winkler, an important man in the old Al Capone gang, to turn the negotiable securities into spending money. But Winkler's fame was such that he was an obvious suspect. He was arrested, and made a deal with the bank and a group of Chicago businessmen who'd started a crime-fighting organization newspapers dubbed "The Secret Six."

To avoid prison, Winkler provided proof that more than $2 million worth of the securities had been destroyed, and he returned almost $600,000 worth of the ones that remained. Officials of the shaky bank announced this cut their loss to between $10,000 and $15,000, but that was mostly in securities that had either been cashed or hadn't yet been recovered.

For Bailey, the robbery fell into the category of "it seemed like a good idea at the time." I guess it was, sort of, because even a 25 per cent return on those securities would have been $700,000. Even divided six ways, that was a fortune in 1930. Instead, the robbers had to concern themselves with their next heist and hope they'd escape with more cash.

HOWEVER, Bailey soon had another task, one that would come back to haunt him. A Chicago acquaintance, Fred "Killer" Burke, indicted for his part in Chicago's 1929 St. Valentine's Day Massacre, spent the rest of that year hiding with Mrs. Viola Brenneman in St. Joseph, Michigan, posing as Mr. and Mrs. Frederick Dane. On December 15, 1929, a local policeman named Charles Skelly stopped Burke after a minor traffic accident, and when the policeman approached his car, Burke shot and killed Skelly with a .45 automatic. He wrecked his car during his escape, but commandeered two others and successfully fled Michigan, leaving his make-believe wife behind.

Needing a new place to hide, Burke tracked down Bailey, who took the fugitive to Sullivan County, Missouri, where he introduced Burke to his mother as Richard White. Bailey soon left Burke, who decided Sullivan County was a safe place to remain indefinitely. Whether he'd brought it with him, had it delivered by some pals, or found a money tree in the middle of nowhere, Burke always seemed to have a lot of cash on hand. That impressed some folks, annoyed others.

Among the former was a 20-year-old student nurse named Bonnie Porter and her parents, who lived not far from Bailey's mother. The 37-year-old Burke married Ms. Porter two weeks after they met, and he moved into her parents' home. The Porters thought Mr. White was a successful businessman, though they weren't sure what his business was. In truth, Burke was wanted for murder in seven states.

A local truck driver named Joseph Hunsaker, a big fan of detective magazines, was suspicious of the newcomer who was so free with his money. Hunsaker also thought Mr. White bore a strong resemblance to a photo of Fred Burke he'd seen in a true crime magazine, though the man in the magazine photo was clean-shaven, the man married to Bonnie Porter had a mustache and looked like he could be Adolf Hitler's pudgy brother.

Hunsaker kept an eye on Mr. White, sought advice from a Sullivan County real estate man, who agreed about the resemblance between Bonnie Porter's husband and the wanted killer, whose capture might lead to $100,000 in reward money from the various municipalities where Burke was wanted.

Finally, Hunsaker contacted the police, ironically choosing to call the department in St. Joseph, Missouri. Four officers went to the Porter house in Milan, Missouri, and arrested Burke, who was in bed. Before being whisked away, Burke gave his wife $300, and suggested she file for divorce. After various jurisdictions conferred, Burke was sent to St Joseph, Michigan, where justice was swift. Just one month after his arrest, Burke was convicted of the murder of policeman Charles Skelly, and sentenced to life at Marquette State Prison. (In July, 1940, at the age of 47, he would suffer a massive heart attack and die in prison.)

Most interestingly, police seemed unaware why Burke had chosen to hide in Missouri, and of his connection with Harvey Bailey, or Tom Brennan, as he was known to his associates. Bailey's real identity would finally surface in 1932.

As for the $100,000 reward, from what I've found online, including an interesting Facebook post by Blytha Dennis Ellis, who seems to know a lot about Missouri history, Joseph Hunsaker never received any money for his efforts, each municipality citing a technicality in the conditions of their reward, mostly that it was offered for Burke's conviction, when, in fact, he wound up pleading guilty to the Michigan murder and never went to trial anywhere else.

Back home in his hometown, Green City, Missouri (population at the time about 800), Hunsaker had been treated like a lottery winner, with folks asking him for money as though he were already rich. Some probably didn't believe how poor he really was, since he had quit his job in anticipation of a big payoff.

BAILEY'S undoing began June 17, 1932 when he robbed a bank in Fort Scott, Kansas. With him were "Pretty Boy" Floyd, Alvin "Creepy" Karpis and, I assume, Freddie Barker, since he and Karpis — real name Karpavicius — were the mainstays of the Barker-Karpis gang that robbed many banks during their rather long run. Their take on the Fort Scott job usually is listed as $32,000, though some sources claim it was $47,000.

No matter. The important thing about this robbery, so far as Harvey Bailey is concerned, is where he went afterward. On July 6, just 19 days after the robbery, Bailey was on a Kansas City golf course with two friends, Thomas Holden and Francis Keating, who just happened to be fugitives, having escaped two years earlier from Leavenworth Prison, where they were serving time for a mail train robbery. And here they were, playing golf on a course just 40 miles from the prison.

Stories vary about why Bailey was there. One says he'd gone to the golf course with Freddie Barker to meet a man who would exchange their Fort Scott loot for cash they could freely spend. This story says the man didn't appear, so Bailey decided to play golf with Holden and Keating, who just happened to be there. Barker didn't play golf, so he left.

I don't believe that story because Bailey showed up at the golf course in knickers, ready to play. The more likely story is Bailey, Holden and Keating had simply scheduled a golf date, and kept it. My favorite story, though I don't believe this one either, is their round of golf began as a foursome, the fourth member being another bank robber, Frank "Jelly" Nash, who enjoyed golf, but happened to be terrible at it, and was left on the fairway or in the rough when his three playmates strolled away from the eighteenth green. If true, which is doubtful, this would make a memorable story more-so, because ...

Minutes after Holden, Keating and Bailey finished their round and headed toward their automobile, they were intercepted by federal agent Raymond J. Caffrey and several Kansas City policemen. Federal officers had been searching for Holden and Keating ever since the two men walked out of Leavenworth on phony trusty passes. After failing to find them elsewhere, they began concentrating efforts on golf courses, knowing the two men were golf fanatics. They never expected to find them so close to Leavenworth, but they received a tip that two men closely resembling the fugitives frequently played at a public course in Kansas City.

Caffrey was oblivious about Bailey, who identified himself as John Brown, and was told to wait in an automobile where two women were waiting. The women identified themselves as Mrs. Holden and Mrs. Keating. (Some stories say there was a third woman in the car, but she was never identified.)

Holden and Keating were taken back to Leavenworth, while the other man in the knickers was held for further questioning after police discovered weapons in the car. They quickly learned "John Brown" was an alias for John J. Brennan, also known as Tom.

Back to "Jelly" Nash: The story about him being part of a foursome with Holden, Keating and Bailey is told in "J. Edgar Hoover and His G-Men," by William B. Brauer. The 1995 book presents it as a rumor that circulated in the underworld, so it should be taken lightly.

If Nash had been on the golf course that day, and if he had been caught, especially by agent Caffrey, then possibly a terrible wrong would have been avoided, and 1933's Kansas City Massacre (aka the Union Station Massacre), one of the most violent and tragic events in the history of Hoover's organization, would have been avoided. (The link will take you to an interview with Robert Unger, whose controversial book about the shoot-out in front of the Kansas City train station challenges — quite convincingly, as far as I'm concerned — the official version of what happened that day.)

As it was, Nash wasn't captured until July, 1933, in Hot Springs, Arkansas. Nash and agent Caffrey, plus three other lawmen, lost their lives after Nash was shuttled from a train to an automobile to be taken to Leavenworth prison. Harvey Bailey, who was nowhere near Kansas City that day, would be among those accused of gunning down Caffrey and the others. In fact, Bailey was briefly considered the leader of the gang that attempted to set Nash free. The man actually in charge that day was Verne Miller.

Years later, Bailey might have looked back on his life and wished he'd never met Holden and Keating, not only for their unfortunate round of golf. Ms. Taylor's piece says years earlier Holden and Keating introduced Bailey to George "Machine Gun" Kelly, and took him along on at least one bank robbery. Bailey and Kelly soon parted company, but in 1933, their paths would cross again, and thanks to Kelly, Bailey would find himself arrested and convicted to a crime he didn't commit.

CAFFREY learned the man who called himself John Brown, J. J. Brennan and Tom Brennan, was actually Harvey Bailey, who admitted that 19 months earlier, he provided a hiding place for Fred Burke.

According to an Associated Press story (July 10, 1932), Bailey admitted he was running liquor from Canada to Chicago when a member of the Chicago syndicate asked him to find a place where Burke could be put for a few weeks. (Many years later, Bailey, working with writer J. Evetts Haley for the book, "Robbing Banks Was My Business: The Story of J. Harvey Bailey," would claim he and Burke were drinking beer in Calumet City, Illinois, when the St. Valentine's Day Massacre occurred. Probably not, but who knows?)

Worse news for Bailey was a visit from employees of the Citizens National Bank in Fort Scott, Kansas, who identified him as one of the men who staged the $32,000 robbery on June 17. Bailey was taken to Fort Scott for trial. While there, an official of National Bank and Trust Company in Lincoln, Nebraska, identified Bailey as one of the men who participated in the 1930 robbery that set a record, but netted the bandits very little real cash.

Meanwhile, Bailey's golfing partners, Thomas Holden and Francis Keating, were dragged into the investigation of the kidnapping of Charles Lindbergh Jr., taking Bailey with them, but that, of course, came to a dead end. It seemed everyone in the country who had a police record was briefly a suspect in the Lindbergh case.

Bailey was convicted in Fort Scott and sentenced to 10 to 50 years at the Kansas State Prison in Lansing. But the big news after the trial was the murder of one of Bailey's lawyers, J. Earl Smith, who apparently had been hired by someone from the Barker-Karpis gang. Smith was beaten and shot, his body found next to his automobile near the Indians Hills Country Club in Tulsa, where the lawyer lived.

Bailey's chief counsel, J. G. Sheppard of Fort Scott, said, "I never heard of Smith until he came into the case. I haven't the least idea who might be his enemies, or the motive in the slaying."

There was speculation he was killed by whoever hired him, punished for Bailey's conviction, though Smith actually had little to do with the case. Nonetheless, in 1936, when J. Edgar Hoover said Smith's murderer had been arrested, it turned out to be Harry Campbell, once a member of the Barker-Karpis gang.

Meanwhile, Bailey went off to Kansas State Prison, and the scene was set for an event the following Memorial Day that would complete the job of turning the man from an anonymous bank robber into the next in line to be called "the most dangerous criminal in America."

New York Sun, May 31, 1933
LANSING, Kansas, May 31 (AP) — Eleven convicts, including three murderers, were at large today, but the six hostages they took in their escape yesterday from the Kansas State Penitentiary, here, were safe.

Warden Kirk Prather, who leaves office today, and two guards, were released last night in the hill country of northeastern Oklahoma, by six of the fleeing prisoners, and returned here today at 7:15 a.m. Three women, whose car was commandeered by the other five convicts, reported today that they were safe at Pleasanton, Kansas, about 100 miles south of Lansing near the Kansas-Missouri border.

One of those 11 escaped convicts was Harvey Bailey. So after just eight months in prison, he again was on the loose. but Bailey's freedom wouldn't last, because weeks later he once again would be in the wrong place at the wrong time.

Meanwhile, he teamed up with the acknowledged leader of the escapees, Wilbur Underhill, nicknamed "The Tri-State Terror." Bailey, Underhill and nine other inmates made their break during a baseball game played at the prison by American Legion teams from Topeka and Leavenworth. Only one thing spoiled the escape — Bailey's right leg was hit by a bullet apparently fired outside the prison by the farm foreman as the convicts were headed for their getaway car with the warden and two other guards as hostages. How badly hurt Bailey was isn't made clear by various stories written about the escape, which has its own page.

Bailey, Underhill and three other escapees — Bob "Big Boy" Brady, Jim Clark and Ed Davis — went on a robbing spree, hitting banks in Black Rock, Arkansas (June 16); Clinton, Oklahoma (July 3), and Kingfisher, Oklahoma (August 9). Since Bailey reportedly participated, it's likely his bullet wound wasn't as serious as reported by warden, Kirk Prather, who was a hostage during the convicts' all-day drive from the Kansas State Prison to Oklahoma.

Prather and the two guards were released near the town of Welch, Oklahoma, and when he talked to an Associated Press reporter on the telephone, Prather said Bailey's right leg was broken below the knee. Since the convicts apparently were headed for Cherokee territory, it was assumed Bailey's leg was treated by a sympathetic Native American doctor.

Whatever, Bailey reportedly was mobile enough less than three weeks later to participate in a bank robbery, but an event elsewhere would prompt him and the other robbers to admit — actually insist — they'd been in Black Rock on June 16.

At the Kansas City train station, just one day after the Black Rock robbery, four law enforcement officers, including federal agent Raymond Caffrey, were gunned down while they were attempting to take previously mentioned outlaw, Frank Nash, to Leavenworth Prison. This event became known as "The Kansas City Massacre" or "The Union Station Massacre." It sparked outrage across the country, and J. Edgar Hoover, head of the organization that soon would become the Federal Bureau of Investigation, vowed to get the men responsible.

The timing of the Kansas penitentiary escape, and the fact two of the men involved were among the Midwest's most famous outlaws, led Hoover to believe Bailey and Underhill may have been two of the shooters in Kansas City. Neither man participated, but the fact they were suspects upped their notoriety considerably. In an effort to persuade Hoover they were not in Kansas City on June 17, Bailey, Underhill and the other members of their gang signed a letter perhaps written by Bailey that confessed to their robbing the bank in Arkansas the day before.

One reason Hoover thought Bailey and Underhill may have attempted to free Frank Nash is because it was widely believed Nash was the source of the guns that were smuggled into the Kansas State Prison to make the Memorial Day escape possible.

Eventually, suspicion would fall elsewhere, as Hoover became convinced the Kansas City shooters were "Pretty Boy" Floyd, Adam Richetti and Verne Miller. I'm not sure Hoover ever admitted he was still wrong. Richetti was convicted for the massacre, but had nothing to do with it; neither did Floyd. Miller, who'd recently moved to Kansas City, was the leader of the gunmen who showed up at Union Station that day. The others — maybe two, maybe three, maybe four — were local gangsters unknown outside of Kansas City. If you click on the Miller story, you'll find what I think is a convincing case that at least three of the five deaths that day were caused by an overeager federal agent unfamiliar with a weapon he may have grabbed by mistake.

But for the rest of the summer, Bailey and Underhill remained on the list of Kansas City suspects, because police shrugged off the letter they had written about the Black Rock robbery.

WHAT HAPPENED next puzzles me, and I've yet to read an explanation that satisfies me. After helping Underhill and the rest of his latest gang rob three banks, perhaps Bailey needed a break. Underhill, apparently, visited his latest wife in the Oklahoma hills, and the other three outlaws went who-knows-where to lie low for awhile. They would reunite a month later for their last bank robbery, but Bailey wouldn't be with them, because he'd chosen to visit a ranch in Paradise, Texas, expecting to find "Machine Gun" Kelly and his wife, Kathryn, whose mother, Ora, was married to "Boss" Shannon, who owned the ranch.

Trouble was, the Kellys weren't there. They were on a trip that included a visit to Cleveland, Ohio, to buy a car with some of the ransom money they received for kidnapping Oklahoma oilman Charles F. Urschel, who'd been held for a week at the Shannon ranch.

You'd think Bailey would have heard through the outlaw grapevine that Kelly was behind the Urschel kidnapping, and that maybe Paradise, Texas, wasn't a good place to visit. But off Bailey went. The Shannons were there and gave Bailey a place to sleep, and sleep he did. The next morning he was arrested by federal agents who'd hoped to find Kelly and his wife at the ranch.

One story is Bailey wanted to return a machine gun he'd borrowed from Kelly. Maybe so. And maybe Bailey was well aware Kelly had kidnapped Urschel and pocketed a huge chunk of the ransom money, because Kelly owned a thousand dollars that Bailey had loaned him two years earlier.

As it was, "Boss" Shannon gave Bailey $640 to tide him over. Bailey claimed he didn't know it was money from the ransom, and when it was discovered by federal agents in one of the outlaw's pockets, that made it easier to convict him for being a party to the Urschel kidnapping. (He'd be given credit or blame — take your pick— for planning the kidnapping, which wasn't true, of course, and must have annoyed "Machine Gun" Kelly, for whom the Urschel snatching was the highlight of an otherwise mediocre criminal career, though many suspected the planning actually was done by Kelly's wife, Kathryn.)

Bailey was taken to Dallas and put in jail pending a move to Oklahoma City to stand trial with others who had been arrested in connection with the Urschel case. (The Kellys were still at large.) Not only that, but Bailey's arrest had prompted some newspapers to describe him as the leader of the Kansas City Massacre.

The Dallas County Jail was selected because it was considered escape-proof. However, Bailey had one more trick up his sleeve, and he played it on September 4, three weeks after his arrest. Like his escape from the Kansas State Penitentiary, this played out like a 1930 James Cagney film — for four hours, anyway.

Buffalo Courier-Express, September 5, 1933
ARDMORE, Oklahoma, September 4 (AP) — Harvey Bailey, one of the nation’s most desperate criminals, was captured at the end of a wild automobile chase here today four hours after he made a sensational escape from the county jail at Dallas, Texas, but using a smuggled pistol.

Cornered in a smashed sedan on a main intersection of the southern Oklahoma city, the accused leader of the $200,000 ransom kidnapping of Charles F. Urschel, Oklahoma City oil man, and one of the asserted machine gunners in the slaying of four officers and Frank Nash, federal convict, at Kansas City, June 17th, surrendered quietly to three Ardmore policemen.

Bailey made no move toward the pistol that lay on a seat beside him.
When the jail car he had stolen at Dallas whirled round a corner and smashed into a curb, Bailey soon found himself looking into the cold muzzles of three Ardmore police pistols.

By his side, protesting, “I’m a jailer,” sat Nick Tresp, Dallas jail turnkey, whom Bailey had kidnapped. It was Tresp’s car that was wrecked beside the curb.

“When we get where we are going,” Bailey had told Tresp during the wild ride, “I’ll give you your car and some money and let you go back.”

Tresp was released by the Ardmore officers as soon as he could be identified; Bailey was taken to jail to be turned over to federal authorities.

Alone and in a fashion matching the daring of the prison break he led from the Kansas State Penitentiary at Lansing on Memorial Day when eleven convicts escaped by kidnapping the warden and two guards, Bailey forced his way through three sawed bars from an isolation cell above the sixth floor of the Dallas jail building and made his way to temporary freedom.

At the direction of Washington department of justice officials, an investigation was begun to determine how Bailey obtained the pistol and the hacksaw with which the bars of his cell had been cut.

Department of justice agents had placed Bailey in the Dallas jail following his recent arrest on a farm near Paradise, Texas, to await removal to Oklahoma City for trial in the Urschel kidnapping.

Joseph B. Keenan, federal anti-crime administrator, who directed the hunt for the desperado from Washington and sent federal agents from several cities by plane to join the search, expressed the belief that “corruption: figured in Bailey’s escape today.

Officials at Dallas and elsewhere expressed amazement that Bailey could have obtained a pistol or escaped from the jail, considered one of the finest in the southwest. Bailey was the first prison in the history of the jail to make a getaway.

Six airplanes from Love Field, the Dallas Municipal Airport, scouted highways in the widespread hunt for the fugitive, but it was an Oklahoma sheriff who spotted Bailey and telephoned ahead to Ardmore where the police took up the trail and ran down the desperado. Taken to a jail cell where he puffed a cigarette, Bailey snarled, “Well, I got out, didn’t I?”

The kidnapper and killer made his getaway at breakfast time. He had managed to saw his way out of an individual cell with a blade mysteriously acquired. When Charley Young, deputy jailer, came with Breakfast, Bailey confronted him in the general enclosure with a pistol as mysteriously acquired as the saw blades. With this pistol he forced Young into a cell, commandeered the jail elevator, kidnapped Tresp and made away with Tresp’s car.

Then the hunt was on. It spread over hundreds of miles. Scores of police cars, armed with all manner of weapons from machine guns to gas bombs, were on the alert.

That was a lot of work for four hours of freedom, all spent in a hijacked car, but it was the big story of the day, and kept Bailey in the headlines. This time federal officers took him to Oklahoma City. It was reported the agents bound Bailey's hands with the blood-flecked handcuffs worn by Frank Nash when he was killed in an agent's car outside the Kansas City railroad station. This time five automobiles were used to transport a prisoner.

R. A. "Smoot" Schmid, sheriff of Dallas County, told reporters he believed the hacksaw blades and pistol were smuggled to Bailey by one of the jail's trusties.

"The old death cell block in which Bailey was held is on the ninth floor of the building. To enter the cell, three doors had to be unlocked. The door to the block is solid steel."

For the first 18 days of Bailey's confinement in Dallas, a rotating team of federal agents, armed with a machine gun, sat outside his cell, watching him around the clock. Then the U. S. department of justice decided it was unnecessary to maintain this close watch on Bailey, who then had four days to receive hacksaw blades and a gun. He sawed through three bars to get out of his cell, and surprised Deputy Charlie Young on September 4 when Young delivered breakfast.

Bailey forced the deputy to lead him out of the cell block and down the stairs to the sixth floor, where the convict locked Young and another deputy in a jail cell, and took the elevator to the ground floor, where he confronted and abducted jailer Nick Tresp.

Four hours later, Bailey was back in custody, but headed for Oklahoma City to face trial along with others who'd been captured in connection with the Urschel case, including Albert L. Bates, who'd been arrested in Denver. Bates, along with "Machine Gun" Kelly, had done the actual kidnapping. And before the trial got underway, Kelly and his wife were located and arrested at a hideout in Memphis, Tennessee, on September 26. They would be tried after the others.

Neither trial produced any surprises.

Syracuse Journal, October 7, 1933
By JAMES L. KILGALLEN
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.”

The next day, October 8, Bailey and Bates, guarded by ten heavily armed officers, were flown in a tri-motored plane from Oklahoma City to the Fort Leavenworth Military Flying Field, then taken by armored car to the prison complex.

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 paroled from federal prison in 1962 and returned to Lansing, Kansas, to serve out his bank-robbing sentence. He released from 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 been found guilty for her involvement 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. She was put on probation, but her husband, Herbert "Deafy" Farmer a was sent to prison.

The Farmers were reunited after he completed a two-year prison sentence 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.

Bailey might have been forever famous if he'd had a more memorable name or a colorful nickname such as "Pretty Boy." The only nickname I found was rather ordinary, and it was given while he worked on the railroad in Iowa, and it was because of a well-known song that became popular a few years earlier. You've probably heard "Won't You Come Home, Bill Bailey," and that's what his co-worked called him.

According to Marilyn Horton Taylor's book-length piece, "George 'Machine Gun' Kelly: His Life and Impact," Bailey developed a strong dislike for Kathryn Kelly, wife of the well-nicknamed outlaw. Bailey didn‘t want women around when he was planning a bank robbery, and he didn't like to talk to women about his business. He found Kathryn Kelly to be aggressively opinionated. There's no doubt she exerted a strong influence over her husband.

However, on October 12,, 1933, in a Newspaper Enterprise Association piece, "Katherine Kelly's Own Story" (notice the misspelling of her first name), she had this to say about Harvey Bailey:

"Yes, I've known him a long time. He's the best of the bunch. You'd take him for a banker. He always was a gentleman, and wanted to do the right thing. He was pretty decent. I never knew him by the name 'Bailey.' He was always Tom Brennan — Big Tim, we called him, and everyone respected him. I honestly don't think his wife, up in Wisconsin, ever knew that the man known as Harvey Bailey was her husband."

That, of course, wasn't true, because she married a man named Harvey Bailey in 1907, and he didn't call himself Tom Brennan for at least 12 years after that.

But speaking of Bailey's first wife, I found nothing on whatever became of her. For all practical purposes, Bailey left Wisconsin for good in 1931, and she stayed there. I did find a mention of Mattie Martin Bailey in the 1910 census, and she was he wife of a Harvey Bailey who was born in West Virginia in 1887. (Apparently he dropped "John" as his first name, or moved it to the middle.) In 1910, the Baileys had no children, though I've seen several stories that said he and Mattie had two sons, who would have been adults by the time he was imprisoned. I assume Mrs. Bailey — or Mrs. Brennan, whichever name she was using — divorced her husband. Whether their sons had any relationship with him years later, I do not know.

On the day Bailey was arrested after his four-hour escape from the Dallas County Jail, an interesting Associated Press item came out of Ithaca, New York.

Sheriff Frank O. Ellis of Tompkins County, NY, “positively identified” a woman hitch-hiker to whom he gave a ride on Saturday, saying she was Dolores Whitney, alleged sweetheart of Harvey Bailey. She gave her name a Rita Kronin, and was with a woman who gave her name as Mitzi Cauzhz. That's right — Cauzhz. The women spent Friday night in Ithaca, headed toward Owego on Saturday, intending to wind up in New York City.

The Brooklyn Daily Eagle soon reported New York City police were looking for Ms. Whitney.

Nothing came of it because I believe someone had played a joke on Sheriff Ellis. It's doubtful Bailey had a sweetheart, especially one who'd be on the road with Kathryn Kelly, who, according to the sheriff in another story was the woman with Ms. Whitney.

Mrs. Kelly was in Memphis with her husband, and the two hitchhikers in the Ithaca area were probably attractive young women in the habit of lying to policemen. The tip-off should have been the name — because Dolores Whitney was an alias Kathryn Kelly used in 1929 when she was arrested for shoplifting in Fort Worth, Texas. Go online and you can see the U. S. Bureau of Investigation (later the FBI) file on Ms. Whitney that features mug shots of Mrs. Kelly.

Bailey robbed at least one bank with Alvin "Creepy" Karpis, so he could be considered a part-time member of the Barker-Karpis gang, supposedly led by Kate Barker, better known as Ma Barker, whose four sons all became criminals.

In his autobiography, "Robbing Banks Was My Business," Bailey poked fun at the idea Ma Barker had any input with gang business. “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.”

Karpis had said pretty much the same thing years earlier, claiming the woman's only role was to tag along, making it appear she were simply a woman on the road with her sons.

In general, Bailey was regarded as an easy-going man, not prone to violence. Though called a killer in several newspaper stories after his 1933 escape from the Kansas State Prison, Bailey never shot anyone. But that escape resulted in conflicting accounts of Bailey's behavior that day. In one, he was a gun-wielding desperado who threatened to kill warden Kirk Prather and the two guards the escaping convicts took hostage; in the other, Bailey saved the lives of the hostages by preventing outlaw Wilbur Underhill from killing them.

Prather's account of the escape says Bailey had a gun and threatened to use it, if necessary, but it was while running to the getaway vehicle that Bailey became the only casualty of the day when he was shot on the right leg. After that, Bailey was in no position to save anyone's life, and needed assistance from other escapees to move around.

Underhill, who was a convicted killer, threatened the warden and the two guards, but released them unharmed several hours after the escape. When he learned the three men, between them, had only loose change in their pockets, Underhill gave them a dollar so they could get something to eat once they walked to the nearest town.

After beginning his life sentence at Leavenworth, Bailey was transferred to Alcatraz, where he remained until 1946. In a 1974 interview with David Dary for an Associated Press story, Bailey, then 86 years old, said he'd known all the notorious outlaws of the 1920s and '30s. "Al Capone was one of the best boys you ever met. I knew him at Alcatraz. He worked with me for three years. I watched over him because some of the punks wanted to stick a knife in him."

Bailey wasn't watching out for Capone on June 23, 1936, when 24-year-old Texas bank robber James Lucas, another Alcatraz inmate, grabbed scissors from the prison barber shop and attacked Capone, who was on a work detail in the prison clothing shop across the hall in the basement. Lucas lunged at Capone and tried to stab him in the back with the scissors, but inflicted only a shallow wound before Capone wheeled around and decked Lucas with a punch. The scuffle was quickly ended when guards intervened. Lucas was sent to solitary confinement, Capone walked to the prison hospital, where his injury was treated.

Capone, never popular with most other inmates at Alcatraz, was targeted because he refused to participate in a prison uprising in January, 1936. Neither did Harvey Bailey or "Machine Gun" Kelly. All three had decided to be on their best behavior behind bars.

Lucas eventually did all right for himself, receiving a presidential commutation of sentence from Richard Nixon in 1970. The ex-convict lived 28 years as a free man before he died in Sacramento in 1998. He was 86 years old.

Capone, only 37 at the time of the attack, already was suffering from syphilis that had gone untreated too long. Diagnosed with syphilitic paresis, Capone soon had uncontrolled rampages at the prison, and for health reasons was released in 1939. Medical treatment afterward helped, but didn't rid Capone of his disease, and he spent the last eight years of his life at his home on Palm Island, Florida, dying in 1947.

Contrary to the opinion of Omaha Detective Inspector G. A. Anderson. who knew Bailey as a young man and didn't consider him very tough, the fifty-something Bailey had quite the opposite reputation at Alcatraz, which may explain why no one tried to stab him after he refused to join a prison riot.

After serving four years at Alcatraz, counterfeiter P. F. Reed, in a 1938 newspaper article commissioned by the San Francisco Chronicle, said Harvey Bailey was "beyond doubt the most dangerous man on the Rock." A year earlier, an anonymous former inmate of Alcatraz, in an article by Alexander Kendrick in the Philadelphia Inquirer, said much the same thing, saying Bailey was one of the three toughest convicts at the prison. (The other two were kidnapper Harmon Whaley and bank robber-kidnapper Volney Davis, who'd been a member of the Barker-Karpis gang.)

Bailey became familiar with the Cookson Hills of Oklahoma, apparently a good place to hide. There he met Charles "Pretty Boy" Floyd. Interviewed in 1974, Bailey says he and Floyd were friends for awhile, and he told a story about the two of them robbing a grocery store in Sallisaw, Oklahoma, loading a truck and delivering the food to "the poor Cherokees and other folks" in the hills.

The version I read said the year was 1924 — when Bailey was 37, Floyd only 20— but other versions have it occurring later. Their friendship, such as it was, was tested after Bailey was arrested in 1933 and was interviewed at the Dallas County Jail. He referred to Floyd as "small fry."

Floyd took offense and wrote a letter to Bailey that was left in an abandoned car after a gun battle in Enid, Oklahoma. He taunted Bailey not only for getting caught, but for surrendering so meekly when he had a pistol next to him and a machine gun under the bed. "I don't carry guns around with me to impress anyone," Floyd wrote."I carry then as a dire necessity. I know some day I am going to lose, but when that time comes, I will not throw up my hands and rely on brains to get me out ... Still I'm outside, while you probably are wracking your brain to beat the chair."

Sure enough, when local police and federal agents led by Melvin Purvis trapped Floyd in a corn field near East Liverpool, Ohio, on October 24, 1934, Floyd was killed in a shoot-out. He was only 30 years old.

And for the next 45 years, Harvey Bailey had the satisfaction on knowing he was still alive, while "Pretty Boy" Floyd was lying six feet under ground.

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