In the shadows
If ever there was a Boogeyman of Depression-era outlaws, it was Wilbur Underhill.
Born Wilber Underhill Jr. on March 16, 1901, this burglar, bank robber and prison escapee was one of the most wanted — and feared — bandits in Oklahoma during the 1920s and ’30s. Known as the "Tri-State Terror" and "Mad Dog," Underhill terrorized the Southwest for nearly a decade — and captured the public’s attention with his deeds.
Arrested and convicted of murder in Oklahoma, he was sentenced to life, but escaped. He then killed a police officer in Kansas, was recaptured, and received another life term. He again escaped, this time leading 10 others in a mass breakout. In the final months of his life, he rose to national notoriety as a suspect in the infamous Kansas City Massacre, and had the dubious distinction of being the first criminal ever shot and killed by agents of a fledgling federal police agency which would soon evolve into the FBI.
True criminal immortality eluded Underhill, however, as his name was eclipsed in the national headlines by such outlaws as John Dillinger, Charles Arthur "Pretty Boy" Floyd, and George "Baby Face" Nelson. But scratch the surface of Oklahoma history even today, and he’s still there, remembered in legend and song.
Early life and criminal career
Underhill was born in Joplin, Mo., one of seven children. His three older brothers, Earl, George and Ernest, all became career criminals — though none gained the notoriety of Wilbur. His three sisters, however, married and led law-abiding lives. When Underhill was 12, his brother George killed a street vendor and was sentenced to life imprisonment. It was shortly after this incident that Underhill began to show his own criminal streak, although his mother claimed that streak was the result of a childhood accident that "Didn’t leave him quite right." He also changed the spelling of his name from Wilber to Wilbur, believing it sounded more manly.
Underhill committed his first known offense by stealing silverware from a neighbor’s home. When questioned by police, he tried to convince them a stranger had given it to him. They didn’t believe him, but lacking evidence, he was released. In 1918, however, he was convicted of burglary and spent four years in prison. A year after his release, a series of armed robberies occurred in remote areas, and the robber was dubbed the "Lovers Lane Bandit." A police decoy eventually caught the bandit, identified as Underhill. This time he was sent to the Missouri State Penitentiary for five years.
Crime spree with Ike "Skeet" Akins
and the murder of George Fee
Soon after his parole in late 1926, Underhill, along with Ike "Skeet" Akins, robbed a drug store in Okmulgee, Okla., on Christmas day. In the course of the robbery, a customer, George Fee, 19, was killed.
Akins and Underhill got away, but were arrested on Jan. 7, 1927, and charged with murder and armed robbery. While awaiting trial, the pair escaped from the Okmulgee jailhouse on Jan. 30 with fellow inmates Red Gann and Duff Kennedy using smuggled hacksaws. Akins was recaptured in Lamar, Mo., on Feb. 9. Three days later, while being returned to Okmulgee, Akins attempted another escape and was killed by Sheriff John Russell.
A day after Akins’ death, Underhill robbed a movie theater for $52 in Picher, Okla. Confronted by Constable George Fuller, he grabbed Fuller’s pistol and killed a deputized civilian, Earl O’Neal, before escaping. Underhill was finally captured on March 20 and returned to Okmulgee where he was convicted on June 3, 1927, of the Fee murder and sentenced to life imprisonment.
Escape and Frank Underhill
Underhill made several attempts to escape from the Oklahoma State Penitentiary before finally succeeding on July 14, 1931. Twelve days later, using the name Ralph Carraway, Underhill purchased a car in Cherryvale, Kan., and later the same day robbed a theater of $300. The following month he recruited his nephew, Frank Underhill, to join him on a crime spree. On Aug. 12, they robbed a Wichita, Kan., gas station for a meager $14.68. A short distance from the robbery, Underhill crashed his car and had to have it towed to a nearby garage. The pair checked into a hotel to await repairs.
The next morning, Patrolman Merle Colver, assigned to check Wichita hotels for suspicious guests, went to their room to question them. When he knocked on the door, Wilbur Underhill shot him three times in the head killing him instantly. Fleeing on foot, Underhill became involved in a running gunfight with police. A 2-year-old boy was killed in the crossfire when police fired at Underhill. He was eventually stopped by a lucky shot to the neck. Underhill was convicted for the murder of Colver, and given another life sentence, and sent to the state prison in Lansing on Sept. 4, 1931. Frank Underhill was not charged and, apparently "scared straight" from his experience, never committed another criminal offense for the rest of his life.
Bailey-Underhill Gang
On May 30, 1933, Underhill participated in a mass escape with 10 others using pistols smuggled in by Frank "Jelly" Nash. Among the escapees were Harvey Bailey, Jim Clark, Frank Sawyer, Ed Davis and Robert "Big Bob" Brady. Several of the escapees joined a gang headed by Underhill and Bailey and went on a six-month crime spree.
On June 17, they robbed a bank in Black Rock, Ark., and the next day Underhill and Bailey were among several fugitives wrongly named as participants in the Kansas City Massacre, a failed attempt to free Frank Nash from police custody, resulting in the deaths of Nash and four lawmen guarding him.
The gang continued its activities and robbed $11,000 from a bank in Clinton, Okla. Two days later, Underhill, apparently acting alone, robbed a bank in Canton, Kan., but rejoined the others to rob a bank in Kingfisher, Okla., on Aug. 9, 1933.
Gang is broken up
Three days after the Kingfisher robbery, Bailey was hiding out on the Texas ranch of Robert "Boss" Shannon, father-in-law of George "Machine Gun" Kelly, when police and federal agents raided the property. Bailey, who had been passed ransom money from Kelly’s kidnapping of oil tycoon Charles Urschel and was in the possession of one of Kelly’s machine guns when arrested, was wrongly convicted in the kidnapping plot two months later. He was given a life sentence.
With Bailey back behind bars, Underhill took charge of the gang. On Oct. 6, he and several others robbed a bank in Baxter Springs, Kan., of $3,000. That robbery was quickly followed by bank raids in Galena, Kan., and Stuttgart, Ark. On Nov. 9, Underhill, Ford Bradshaw and several others raided an Okmulgee bank and escaped with $13,000.
Underhill was now attracting national media attention. He had been called "Mad Dog" or the "Tri-State Terror" by several newspapers. One even dubbed him "The Southwest Executioner."
A special task force was formed, and an extensive search was made of Oklahoma’s Cookson Hills, where he was known to be hiding.
On Nov. 18, with the task force in the area, Underhill quietly walked into the courthouse in nearby Coalgate and applied for a marriage license under his own name. His fiancee was Hazel Jarrett Hudson, a sister of the outlaw Jarrett brothers. The following day, Underhill and several others robbed a bank in Frankfort, Ky.
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Born Wilber Underhill Jr. on March 16, 1901, this burglar, bank robber and prison escapee was one of the most wanted — and feared — bandits in Oklahoma during the 1920s and ’30s. Known as the "Tri-State Terror" and "Mad Dog," Underhill terrorized the Southwest for nearly a decade — and captured the public’s attention with his deeds.
Arrested and convicted of murder in Oklahoma, he was sentenced to life, but escaped. He then killed a police officer in Kansas, was recaptured, and received another life term. He again escaped, this time leading 10 others in a mass breakout. In the final months of his life, he rose to national notoriety as a suspect in the infamous Kansas City Massacre, and had the dubious distinction of being the first criminal ever shot and killed by agents of a fledgling federal police agency which would soon evolve into the FBI.
True criminal immortality eluded Underhill, however, as his name was eclipsed in the national headlines by such outlaws as John Dillinger, Charles Arthur "Pretty Boy" Floyd, and George "Baby Face" Nelson. But scratch the surface of Oklahoma history even today, and he’s still there, remembered in legend and song.
Early life and criminal career
Underhill was born in Joplin, Mo., one of seven children. His three older brothers, Earl, George and Ernest, all became career criminals — though none gained the notoriety of Wilbur. His three sisters, however, married and led law-abiding lives. When Underhill was 12, his brother George killed a street vendor and was sentenced to life imprisonment. It was shortly after this incident that Underhill began to show his own criminal streak, although his mother claimed that streak was the result of a childhood accident that "Didn’t leave him quite right." He also changed the spelling of his name from Wilber to Wilbur, believing it sounded more manly.
Underhill committed his first known offense by stealing silverware from a neighbor’s home. When questioned by police, he tried to convince them a stranger had given it to him. They didn’t believe him, but lacking evidence, he was released. In 1918, however, he was convicted of burglary and spent four years in prison. A year after his release, a series of armed robberies occurred in remote areas, and the robber was dubbed the "Lovers Lane Bandit." A police decoy eventually caught the bandit, identified as Underhill. This time he was sent to the Missouri State Penitentiary for five years.
Crime spree with Ike "Skeet" Akins
and the murder of George Fee
Soon after his parole in late 1926, Underhill, along with Ike "Skeet" Akins, robbed a drug store in Okmulgee, Okla., on Christmas day. In the course of the robbery, a customer, George Fee, 19, was killed.
Akins and Underhill got away, but were arrested on Jan. 7, 1927, and charged with murder and armed robbery. While awaiting trial, the pair escaped from the Okmulgee jailhouse on Jan. 30 with fellow inmates Red Gann and Duff Kennedy using smuggled hacksaws. Akins was recaptured in Lamar, Mo., on Feb. 9. Three days later, while being returned to Okmulgee, Akins attempted another escape and was killed by Sheriff John Russell.
A day after Akins’ death, Underhill robbed a movie theater for $52 in Picher, Okla. Confronted by Constable George Fuller, he grabbed Fuller’s pistol and killed a deputized civilian, Earl O’Neal, before escaping. Underhill was finally captured on March 20 and returned to Okmulgee where he was convicted on June 3, 1927, of the Fee murder and sentenced to life imprisonment.
Escape and Frank Underhill
Underhill made several attempts to escape from the Oklahoma State Penitentiary before finally succeeding on July 14, 1931. Twelve days later, using the name Ralph Carraway, Underhill purchased a car in Cherryvale, Kan., and later the same day robbed a theater of $300. The following month he recruited his nephew, Frank Underhill, to join him on a crime spree. On Aug. 12, they robbed a Wichita, Kan., gas station for a meager $14.68. A short distance from the robbery, Underhill crashed his car and had to have it towed to a nearby garage. The pair checked into a hotel to await repairs.
The next morning, Patrolman Merle Colver, assigned to check Wichita hotels for suspicious guests, went to their room to question them. When he knocked on the door, Wilbur Underhill shot him three times in the head killing him instantly. Fleeing on foot, Underhill became involved in a running gunfight with police. A 2-year-old boy was killed in the crossfire when police fired at Underhill. He was eventually stopped by a lucky shot to the neck. Underhill was convicted for the murder of Colver, and given another life sentence, and sent to the state prison in Lansing on Sept. 4, 1931. Frank Underhill was not charged and, apparently "scared straight" from his experience, never committed another criminal offense for the rest of his life.
Bailey-Underhill Gang
On May 30, 1933, Underhill participated in a mass escape with 10 others using pistols smuggled in by Frank "Jelly" Nash. Among the escapees were Harvey Bailey, Jim Clark, Frank Sawyer, Ed Davis and Robert "Big Bob" Brady. Several of the escapees joined a gang headed by Underhill and Bailey and went on a six-month crime spree.
On June 17, they robbed a bank in Black Rock, Ark., and the next day Underhill and Bailey were among several fugitives wrongly named as participants in the Kansas City Massacre, a failed attempt to free Frank Nash from police custody, resulting in the deaths of Nash and four lawmen guarding him.
The gang continued its activities and robbed $11,000 from a bank in Clinton, Okla. Two days later, Underhill, apparently acting alone, robbed a bank in Canton, Kan., but rejoined the others to rob a bank in Kingfisher, Okla., on Aug. 9, 1933.
Gang is broken up
Three days after the Kingfisher robbery, Bailey was hiding out on the Texas ranch of Robert "Boss" Shannon, father-in-law of George "Machine Gun" Kelly, when police and federal agents raided the property. Bailey, who had been passed ransom money from Kelly’s kidnapping of oil tycoon Charles Urschel and was in the possession of one of Kelly’s machine guns when arrested, was wrongly convicted in the kidnapping plot two months later. He was given a life sentence.
With Bailey back behind bars, Underhill took charge of the gang. On Oct. 6, he and several others robbed a bank in Baxter Springs, Kan., of $3,000. That robbery was quickly followed by bank raids in Galena, Kan., and Stuttgart, Ark. On Nov. 9, Underhill, Ford Bradshaw and several others raided an Okmulgee bank and escaped with $13,000.
Underhill was now attracting national media attention. He had been called "Mad Dog" or the "Tri-State Terror" by several newspapers. One even dubbed him "The Southwest Executioner."
A special task force was formed, and an extensive search was made of Oklahoma’s Cookson Hills, where he was known to be hiding.
On Nov. 18, with the task force in the area, Underhill quietly walked into the courthouse in nearby Coalgate and applied for a marriage license under his own name. His fiancee was Hazel Jarrett Hudson, a sister of the outlaw Jarrett brothers. The following day, Underhill and several others robbed a bank in Frankfort, Ky.
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UJnderhill shows evidence of the neck wound.
