Those who have written about Wilbur Underhill, a Missouri-born outlaw who surfaced in the 1920s and attracted nationwide attention in 1933, speculate on why he didn't become more famous, since he was considered one of the most brazen and dangerous criminals of his era.

The photo above makes him look jaunty, and inspired one writer to say Underhill had Hollywood good looks. Newspapers at the time more often used a photo (right) that made Underhill uglier and more menacing. I think it was taken in 1927 after he had been wounded during a shootout that led to his capture.

One reason suggested not only for the failure of Underhill — and a few other outlaws — to catch public fancy was the lack of a catchy name, though I suggest anyone nicknamed "Mad Dog" and "The Tri-State Terror" stands out from the crowd. And there certainly was a crowd of outlaws in the early 1930s, only some of whom I've spotlighted.

Many of these outlaws are linked, because the rosters of their gangs were ever-changing. In sports terms, Midwest and Southwest outlaws were the free agents of their day. And the more time an outlaw spent in prison, the more known associates he was apt to have.

This led police to assume guilt by association. In 1933, for example, Underhill and ten other inmates escaped the Kansas State Penitentiary in Lansing, using pistols supposedly smuggled into the prison by Frank Nash, who was captured shortly thereafter.

Nash was killed a few weeks after the prison escape when at least three gunmen tried to rescue him from police at Kansas City's Union Station. Four lawmen also were killed in what became known as "The Kansas City Massacre" (or "The Union Station Massacre"). Some assumed Underhill and another Kansas escapee, Harvey Bailey, were two of the shooters outside of Union Station, attempting to free Nash in payment for arranging to have guns smuggled into them at the Kansas prison.

In truth, Underhill and Bailey were busy elsewhere that day, though they were listed as suspects for several months. (Federal authorities, soon to be called the FBI, eventually settled on Verne Miller, Charles "Pretty Boy" Floyd and Adam Richetti as the shooters, though there's considerable doubt about Floyd and Richetti.)

BUT I'M GETTING ahead of myself. Back to "The Tri-State Terror." (Those three states, incidentally, were Missouri, Kansas and Oklahoma.)

Henry Wilber Underhill was born March 16, 1901, near Joplin, Missouri, a town that pops up often in tales about 1930s outlaws. For example, Clyde and Buck Barrow briefly went into hiding there, and had to shoot their way out of town; Bailey settled there after serving time, marrying ex-con Esther Farmer, who years earlier had retired there.

At some point Underhill decided to go by his middle name, but preferred to spell it "Wilbur," because he thought it made the name more masculine.

Jailed for the first time in 1918, Wilbur Underhill resumed his life of crime upon his release in 1922 when he became known as Joplin's "Lover's Lane Bandit," for preying on couples parked in secluded places. He was back in prison by the end of the year. In 1926 Wilbur and his three brothers had a family reunion at the Missouri State Prison in Jefferson City.

Hornell (NY) Tribune-Times, May 3, 1926
JEFFERSON CITY, Missouri — Four brothers, serving terms in the penitentiary here, furnish criminologists with an interesting study. The brothers, member of the Underhill family of Neosho, Newton County, Missouri, are serving terms ranging from attempted robbery to murder. A stepson of their sister is also an inmate of the same prison.

The fourth brother, George Underhill, 22 years old, was dressed in recently at the prison to serve five years for burglary and larceny from Newton County after his brother, Earl, had testified against him.

Charles E. Underhill, now 32, has been in prison since November, 1913, serving a life sentence for murder.

Wilbur Underhill, 25, is serving his second term. His first term was two years from Newton County for attempted robbery. He was released in December, 1921, but was returned February 2, 1923, to serve five years for first degree robbery.

The oldest brother, Earl, 36, was received here last December to serve two years for burglary and larceny from Newton County. He was given credit for his jail time in Neosho..

Earl incurred the enmity of his family and brothers because he testified against George.

Earl said he left home when he was 15 years old and spent most of his time in the west as a carpenter. He returned to Missouri at intervals on visits to his family and his wife’s family.

He said he arrived in Joplin on May 22, 1925,, for a visit with his mother. The following day his youngest brother, George, asked him to use his automobile in hauling some stolen tires from a garage in Neosho. Earl, who said he had never been in trouble before, realized that he did wrong in using his car to haul the stolen property.

In the party stealing the tires was Morris Baine, 22, stepson of a sister of the Underhill brothers.

After remaining in jail five months, Earl told the officers the complete story of the robbery and pleaded guilty to the burglary and larceny charge. His testimony later resulted in George getting a five-year sentence and Baine seven years.

The father of the boys was a farmer and carpenter in Newton County. There were four boys and three girls in the family. The father died several years ago.

George Underhill, the youngest of the seven children, died first, in 1931, after breaking out of jail, robbing two pharmacies, and taking an overdose of sodium amytal.

Charles was better known by his middle name, Ernest, which was often spelled Earnest. He died of cirrhosis in 1937.

Earl, the oldest, spent time in prison, but wasn't a career criminal, and after his 1926 spent the rest of his life as a law-abiding citizen, dying in 1974, at the age of 85.

His sister Grace Underhill Baine also died in 1974. She was 86.

Another sister, Anna, married a man named Lewis, and in 1973 was living in Joplin.

The seventh child of Henry and Almira Underhill was Dorothy, who never married. She moved to Kansas City, cared for her widowed mother, and worked for the Jackson County liquor control board. Her mother died in 1951, Dorothy died 20 years later.

This information came from an article in the Kansas City Times on December 29, 1973.

WILBUR UNDERHILL was paroled a few months after the above 1926 article appeared, and committed his first murder in December during a drug store robbery in Okmulgee, Oklahoma, when he shot the teenager who walked into a drug store he was robbing with his partner, Ike "Skeet" Akins.

Caught, Underhill then escaped jail, was recaptured, tried and sentenced to life in the Oklahoma State Penitentiary at McAlester, but he escaped on July 14, 1927, committed more robberies, was confronted by a policeman — and committed his second murder, taking a bullet in the neck in the process. This time he wound up in the Kansas State Penitentiary in Lansing.

He escaped in 1931, was caught, and, less than a month after he was returned to prison, was in the news again when the warden, Kirk Prather, announced on September 16 that a convict serving a life sentence had come forward with information about a breakout plot involving nine inmates. And though this plan had been in the works for months, the new ringleader, according to the warden, was Wilbur Underhill.

This plot had all the makings of a movie. The inmates had manufactured three shotguns, a revolver and ammunition in a prison machine shop, and also had a rifle that had been smuggled to them from outside. Warden Prather led the raid that uncovered the cache of weapons, hidden in a machine shop wall. The nine convicts had come up with a list of six guards and inmate trusties to kill on their way out of the prison.

At the time, Prather withheld the name of the inmate who talked, but two months later, a convict named Stanton Zack, serving a life sentence under the Kansas Habitual Criminal Act, was paroled as a reward for the information he provided.

A year later, another breakout was nipped in the bud, though this time Underhill's name wasn't mentioned. Instead, the leader of the plot was a convict known as "Two Gun" Henderson.

However, Wilbur Underhill still had escape on his mind. He put his next plan in motion on Memorial Day, 1933, while a baseball game was being played inside the walls of the Kansas State Prison. Underhill was about to become nationally famous when he and ten other inmates escaped during the fifth inning of what was supposed to be the first game of a double-header between two area American Legion teams. The convicts abducted the prison warden and two guards, who accompanied Underhill and five other escapees during their long drive to Oklahoma. The other five convicts commandeered another car.

Underhill either couldn't drive or didn't like to, because he always put another gang member behind the wheel.

Meanwhile, what immediately became known as "The Bailey-Underhill Gang" — which included three of the inmates who rode to Oklahoma with Underhill — robbed banks in Black Rock, Arkansas (June 16); Clinton, Oklahoma (July 3), and Kingfisher, Oklahoma (August 9). Gang members then went off in different directions — perhaps it was a split, perhaps just a time out, no one will ever know because Bailey chose to visit George "Machine Gun" Kelly in Paradise, Texas, at the ranch of Mr. and Mrs. R. G. “Boss” Shannon. (Mrs. Shannon was Kelly's mother-in-law.)

A few weeks before Bailey's visit, Kelly and his partner in crime, Albert Bates, had kidnapped Oklahoma oilman Charles F. Urschel and kept him at the ranch before collecting a $200,000 ransom.

It was a careless move by Bailey, who should have expected federal agents might know who had kidnapped Urschel, and where they might have held him, though Bailey couldn't have anticipated how an unusually aware Urschel had helped police pinpoint the location.

Kelly and his wife were many miles away, so when Bailey showed up at the ranch on August 11, he was greeted by "Boss Shannon and Ora, who gave him a place to stay, plus $640 of the thousand dollars Kelly owned Bailey on an old loan. Bailey must have been very tired, because he was still asleep the next morning when federal agents showed up and arrested him and the Shannons in connection with the Urschel kidnapping.

Meanwhile, Underhill was in Oklahoma with his latest wife, intent on robbing more banks after a brief rest. According to "The Tri-State Terror," by R. D. Morgan, Underhill would have have sex with a woman unless they were married. Apparently, his idea of foreplay was saying the wedding vows. Thus he married five women, but divorced none of them.

Syracuse American, September 24, 1933
STUTTGART, Arkansas (INS) — A machine gun bandit who bragged he was Machine Gun Kelly, but who was identified from photographs as Wilbur Underhill, a cop killer, was sought today after robbing the People’s National Bank of $1,000.

The bandit stepped into the bank with two companions and waving a machine gun and shouted, “I’m Machine Gun Kelly! You’ve read about me!”

He ordered Mrs. Joan Morgan, an employee, to open the safe, but she protested she did not know the combination. He then scooped up about $1,000 from the teller’s cage and forced Mrs. Morgan and other employees and a customer to his car. The three bandits used the women as shields, making them stand on the running board to protect the bandits from bullets from any pursuing officers.

Underhill and the three remaining gang members who had escaped from the Kansas State Prison on Memorial Day parted company after the Stuttgart robbery. Ed Davis and his wife moved to California. Bob "Big Boy" Brady and Jim Clark attempted their own crime spree, in Oklahoma and Texas, but soon had to flee into New Mexico.

Syracuse Journal, October 7, 1933
TUCUMCARI, New Mexico (INS) — Bob “Big Boy” Brady, an escaped Kansas convict, was near death in a Tucumcari hospital today after being shot down by Sheriff Ira Allen while fleeing arrest.

Brady was arrested while driving into Tucumcari from Amarillo, Texas, with a man tentatively identified as Jim Clark, another escaped convict, who was arrested.

Clark and Brady offered no resistance when Sheriff Allen ordered them to halt their car. Instead, Brady leaped from the car and fled down the road. Sheriff Allen and a deputy fired simultaneously. Brady dropped, hit three times.

Both men took part in the Kansas state prison riot last Memorial Day and escaped.

Clark at first was believed to be Wilbur Underhill.

Brady, who took a shot in the head, managed to survive. He and Clark were sent back to the Kansas prison in Lansing, but — surprise! — they escaped again on January 19, 1934.

This time they split. Brady, perhaps suffering the effects of his October gunshot wounds, which had impaired his vision, was killed in a shootout five days later near Paola, Kansas.

Clark and another escaped convict, Frank Delmar, soon robbed a bank in Goodland, Kansas, but Clark was shot in both feet by a policeman. He escaped but was sidelined for three months, before the next bank robbery, in Wetumka, Oklahoma.

However, Clark's luck ran out in August when he was arrested on federal bank robbery charges. Found guilty, he spent the next 35 years bouncing between Leavenworth and Alcatraz, before being sent to Seagoville, Texas, where he was released in 1969.

At 67, Clark married his late brother's widow, lived in Oklahoma, worked as a ranch hand and managed a parking lot until he died June 9, 1974.

However, even Brady, killed 40 years earlier, managed to outlive Wilbur Underhill:

Buffalo Courier-Express, December 31, 1933
SHAWNEE, Oklahoma, December 30 (AP) — The “Tri-State Terror,” Wilbur Underhill — killer, bank robber, machine gunner and prison breaker — lay in a dying condition tonight, his body almost riddled by police bullets, and law enforcement agencies checked off another name on the dwindling list of southwestern bad men still at large.

“I don’t think I can live,” he told his bride, a pretty brunette whom he married at Coalgate, Oklahoma, several weeks ago.

Hospital physicians expressed the belief the outlaw would not live, and officers voiced amazement that Underhill had been able to escape from a house where he was trapped and wounded in a gunfight early today.

Bleeding from more than half a dozen wounds, and scantily clad, Underhill ran from the house under a hail of lead and found refuge in a furniture store.

Four hours later he was found hiding in a bed in the rear of the store. He surrendered without a fight, although still armed with a pistol.

Underhill was a leader of the break of eleven convicts from the Kansas penitentiary last Memorial Day, and is under indictment for the machine gun killing of four officers and Frank Nash, federal convict, at Kansas City last June.

R. H. Colvin, department of justice agent from Oklahoma City, and a group of other officers trailed Underhill to the house.

Captured in the raid were a man tentatively identified as Raymond Roe, alias Ralph Rowe; a Seminola beauty parlor operator, Eva Mae Nichols, and Underhill’s wife, the former Hazel Hudson.

Roe was wounded in the right shoulder by the officers’ fusillade, fired when Underhill grabbed two pistols as Colvin peered through a rear window and shouted, “Stick ‘em up, Wilbur!”

The Nicholas woman was shot through the stomach and probably fatally wounded.

Sobbing at her husband’s bedside, Mrs. Underhill said, “Wilbur’s a good man and he’s been trying to go straight, but they just won’t let him.”

The bandit’s wife wore several large diamonds when taken to the hospital to see her husband. She was attractively dressed.

Assuring his wife the officers “have nothing against you,” Underhill told her where she could find his automobiles and valuable papers.

But the only “valuable papers” officers had located were $5,300 in bonds of the Franklin Title and Trust Company of Kentucky, found in the outlaw’s clothing after he staggered from the raided house.

A light was burning in a bedroom. Colvin and Clarence Hurt, Oklahoma city policeman, cautiously approached an open window after other officers had surrounded the house.

“Colvin and I walked up to the window of a northeast bedroom in the house,” Hurt said. “There was Underhill standing near the bed in his underwear, and his wife was sitting on the bed.”

Colvin was armed with a machine gun, Hurt with a machine gun and a tear gas gun.

When the officers shouted at him to surrender, Underhill whirled, grabbed two automatic pistols off a small table and fired.

His first shot brought a rain of lead from the posse men’s machine guns, shotguns, rifles and revolvers. The officers shot not only into the Underhill room, but into the adjoining room, which was dark. That’s where Roe and the Nichols woman were.

“We saw Underhill stagger when the volley opened,” said Hurt. “Then he jumped into another room. His wife fainted.”

The firing lulled, then Underhill darted from the front door and ran across muddy ground into the darkness. He disappeared behind another house.

Hurt estimated 200 shots were fired. He said he believed Underhill fired at least 60 of them. None of the officers was wounded.

With Underhill’s capture, all except one of the eleven persons indicted for the Kansas City killings have been arrested or slain. The man still sought is Richard T. Galatas, Hot Springs, Arkansas, gangster.

Only one of the eleven convicts who escaped from the Kansas prison on Memorial Day is at large. He is Ed Davis. All of the other fugitives have been recaptured or killed.

Underhill’s capture had been expected for weeks. Some time ago, he escaped an early night raid on the farm home of George Nash, near Konawa, 30 miles southeast of Shawnee. At that time he left the farmhouse scantily clad and ill.

While officers were reticent as to the clues leading to the desperado’s apprehension, it was disclosed that one clue came indirectly through the Nichols woman after Underhill went to her shop in Seminole to be treated by a doctor following the Konawa escape.

Underhill gained his nickname, “The Tri-State Terror,” through his viciousness as a killer and his widespread criminal operations through Oklahoma, Kansas and Missouri.

He was serving a life sentence for the murder of Merle Colver, Wichita, Kansas, policeman, when he escaped from the Kansas penitentiary last May 30 by kidnapping the warden. He led the break with Harvey Bailey, now serving a life sentence in Leavenworth federal penitentiary for the $200,000 ransom kidnapping of Charles F. Urschel, Oklahoma City oil millionaire.

Underhill had escaped from the Oklahoma penitentiary in July, 1931. He then was serving a life sentence for murder in Okmulgee County. The murder of a boy in Picher, Oklahoma, also is charged against him, as well as numerous bank robberies.

There's an interesting story about Wilbur Underhill's last days; you'll find it on a website called Baby Face Nelson Journal.com. For a look, see "Shawnee Ambush."

For the short version, keep reading. Underhill was taken to a hospital and manged to hang in there until January 6, when he was returned to the Oklahoma State Prison in McAlester. He died en route. His bride — who was, at least, the fifth Mrs. Underhill, probably was soon released from police custody. Nichols, who was married, but hoping for a divorce, died of her gunshot wounds. Roe recovered and was returned to prison.

Ford Bradshaw, a young outlaw and a partner of Wilbur Underhill during the "Terror's" last few bank robberies, shot up the tiny town of Vian, Oklahoma, on New Year's Eve to vent his anger over Underhill's capture, but Bradshaw would be dead before April, killed by a deputy sheriff in Ardmore, Oklahoma, while resisting arrest.

Underhill remained linked to two outlaws who'd make news before long.

Raymond (aka Ralph) Roe wound up in Alcatraz where he teamed with another former Oklahoma convict, Theodore Cole, to attempt an escape from the escape-proof island prison. They sneaked out on December 16. 1937, and disappeared into a heavy fog on flotation devices they had fashioned.

Experts on tidal current said there was no chance Roe and Cole could have survived, that they would have been swept into the Pacific Ocean with no chance of reaching shore beforehand. It was no surprise their bodies were never found ... but because their bodies were never found, some people believed they lived to talk about their escape.

Exactly one year later, in California's San Quentin Prison, Ed Davis, 38, who had escaped with Wilbur Underhill from the Kansas State Prison in 1933, was executed in the gas chamber.

Davis had been arrested soon after fleeing to California, but in September, 1937, he and four other inmates tried to escape from Folsom Prison. During the failed attempt, warden Clarence Larkin was killed.

The five convicts were sentenced to death a few weeks later, but appeals delayed the executions. Davis was the last of the five to die. The first two, Albert Kessell and Robert Cannon, died a week earlier, the first convicts to be executed in California's gas chamber.

By that time, "The Tri-State Terror" had pretty much faded from memory.


The usual advisory applies. The stories of Wilbur Underhill and other outlaws of the 1920s and '30s may, in general, be accurate, but several details likely are more fiction than fact.