Wilbur Underhill – The Tri State Terror

In the turbulent years of the Great Depression, a wave of outlaw violence swept across the American Midwest and South, as economic hardship and weakened law enforcement allowed criminals to operate with unprecedented boldness. Among the most feared of these Depression-era bandits was Wilbur Underhill Jr., a man whose violent life, remarkable escapes, and dramatic end cemented his place in criminal folklore. Known by chilling nicknames such as “Mad Dog,” the “Tri-State Terror,” and the “Southwest Executioner,” Underhill was more than a bank robber—he was a symbol of lawlessness during one of America’s most chaotic periods 1. His repeated confrontations with the justice system, mastery of evasion, and ultimate demise in a brutal shootout with federal agents marked a turning point in American law enforcement. This report explores the life, crimes, and legacy of Wilbur Underhill in depth, drawing on historical records and contemporary accounts.

Early Life: A Family of Outlaws

Wilbur Underhill Jr. was born on March 16, 1901, in Joplin, Missouri, into a family where crime was all too familiar 1. He was one of seven children, three of whom—his older brothers Earl, George, and Ernest—became career criminals themselves. Though none achieved the level of infamy that Wilbur would, the environment in which he was raised undoubtedly shaped his trajectory.

When Underhill was just 12 years old, his brother George killed a local peanut vendor and was sentenced to life in prison. This incident, often mistakenly attributed to Wilbur himself, underscored the violent undercurrents within the Underhill family 1. Wilbur’s mother later claimed that a childhood accident had left him “not quite right,” possibly indicating neurological or behavioral issues, though this remains anecdotal 1. Regardless, by adolescence, Wilbur had already begun testing the bounds of the law, starting with petty theft—such as stealing silverware from neighbors—and concocting elaborate stories to avoid detection.

He was first convicted in 1918, at age 17, on a burglary charge, and sentenced to four years in prison. After his release, he became locally known as the “Lovers Lane Bandit” for a series of robberies targeting couples parked in secluded areas. His criminal identity was soon revealed after he was caught in a police sting operation and sent back to the Missouri State Penitentiary for five additional years on an armed robbery conviction 1.

The Making of a Murderer

Underhill’s first major descent into violent crime began in 1926 after he was released on parole. On Christmas Day of that year, he and his accomplice Ike “Skeet” Akins robbed a drug store in Okmulgee, Oklahoma. During the robbery, a 19-year-old customer named George Fee was fatally shot—a killing that Underhill was later convicted of despite claims that Akins was responsible 1.

Both men were arrested on January 7, 1927, but while awaiting trial, they orchestrated a daring jailbreak. With smuggled hacksaws, Underhill and three other inmates—including Akins—cut through cell bars and escaped from the Okmulgee jail. Akins was recaptured shortly thereafter and, on February 12, was shot and killed by Sheriff John Russell during a second escape attempt. Underhill, however, evaded capture and went on a brief crime spree, including robbing a movie theater in Picher, Oklahoma.

Confronted by Constable George Fuller during this robbery, Underhill seized the officer’s pistol and killed a deputized civilian, Earl O’Neal. He was captured a few weeks later in Panama, Oklahoma, and returned to face trial. On June 3, 1927, he was convicted of George Fee’s murder and sentenced to life imprisonment at the Oklahoma State Penitentiary 1.

Escapes, Murders, and Escalating Notoriety

Wilbur Underhill’s reputation as a master escape artist was born not from exaggeration, but from repeated success. He escaped from the Oklahoma State Penitentiary on July 14, 1931, after multiple failed attempts. Twelve days later, he robbed a theater in Cherryvale, Kansas, under the alias Ralph Carraway. In August, he recruited his 16-year-old nephew, Frank Underhill, and embarked on another crime spree 1.

After a botched robbery at a Wichita gas station, where they netted just $14.68, the pair checked into a local hotel. Patrolman Merle Colver, assigned to look for suspicious guests, approached their room. Without warning, Underhill opened the door and shot Colver three times in the head, killing him instantly 1. A fierce gunfight erupted on the streets of Wichita as Underhill fled on foot. Tragically, a 2-year-old boy was caught in the crossfire and killed 1.

Underhill was eventually wounded by a shot to the neck and captured. Convicted of Colver’s murder, he was sentenced to another life term and sent to Lansing State Prison in Kansas. Though he claimed the shooting was an accident, witnesses confirmed a deliberate and cold-blooded execution 1.

The Bailey-Underhill Gang and the 1933 Crime Spree

By 1933, Underhill had become one of the most notorious outlaws in Oklahoma. His legend grew during a mass prison escape from Lansing on May 30, 1933. The breakout was made possible by smuggled pistols arranged by the infamous Frank “Jelly” Nash, another Depression-era gangster. Among the escapees were outlaws such as Harvey Bailey, Jim Clark, Ed Davis, Robert “Big Bob” Brady, and Frank Sawyer—names that would become synonymous with the criminal underground of the era 1.

The group formed a core within the emerging Bailey-Underhill Gang, a mobile and violent criminal enterprise that targeted banks across state lines. Their spree began with a robbery of $5,000 from a bank in Black Rock, Arkansas, on June 16, 1933. Despite being wrongly accused of involvement in the Kansas City Massacre—a deadly ambush that killed four law enforcement officers and Nash himself—Underhill continued to expand his criminal portfolio 1.

When Harvey Bailey was captured during a raid on Machine Gun Kelly’s father-in-law’s ranch in Texas, Underhill assumed full leadership of the gang. Under his direction, the group targeted banks in Kingfisher and Clinton, Oklahoma, and continued operations in Baxter Springs and Galena, Kansas. In a surprising and brazen act, Underhill applied for a marriage license in Coalgate, Oklahoma, under his real name on November 18, 1933 1. His fiancée was Hazel Jarrett Hudson, sister of another family of outlaws, the Jarrett brothers.

As a “wedding present” for Hazel, Underhill led his gang in a bank robbery in Frankfort, Kentucky, shortly after the ceremony 1. The act symbolized both his lack of remorse and his flair for the dramatic—a hallmark of his criminal identity.

Pursuit by the FBI

The FBI, frustrated by the piecemeal efforts of local law enforcement, assigned Special Agent R.H. Colvin to lead the investigation into Underhill 3. Colvin discovered a critical lead: Underhill had provided his wife’s address in Oklahoma City to a minister in order to receive their marriage certificate. This lapse in caution allowed federal agents to stake out the home, hoping to apprehend Underhill upon his return.

However, the Underhills arrived, spotted the surveillance, and fled before reinforcements could arrive 1. A later raid on a farm near Konawa, Oklahoma, where Underhill was believed to be staying, ended in failure after Underhill passed the officers on the road and escaped undetected.

The gang continued its operations, robbing a bank in Harrah, Oklahoma, on December 11, 1933, and striking again in Coalgate two days later 1. The FBI, local police, and state troopers launched an intensified manhunt, culminating in a decisive operation in late December.

The Final Showdown in Shawnee

On December 26, 1933, Wilbur and Hazel Underhill were honeymooning at a rented cottage in Shawnee, Oklahoma, accompanied by Underhill’s associate Ralph Roe and Roe’s girlfriend, Eva May Nichols. Four days later, on December 30, a 24-man strike force composed of federal agents, state troopers, and local lawmen surrounded the house 3. The team, led by Agent Colvin and Frank Smith, a survivor of the Kansas City Massacre, ordered Underhill to surrender.

Instead, Underhill opened fire. A fierce and chaotic shootout ensued, lasting several minutes. Tragically, Eva Nichols, an innocent bystander, was killed in the crossfire. Underhill, barefoot and in his underwear, fled the cottage while being shot five times. Despite his injuries, he managed to run 16 blocks before breaking into a furniture store and collapsing on one of the beds. He was discovered there, unconscious and bleeding 1.

Ralph Roe, also wounded, was captured at the scene. Hazel Underhill was taken into custody unharmed. Wilbur was transported to the prison hospital at the Oklahoma State Penitentiary in McAlester, where he remained handcuffed to his bed during his final days 2.

He died on January 6, 1934, at the age of 32. According to multiple sources, his final words were: “Tell the boys I’m coming home”—a grim farewell that reflected a life lived among outlaws 1. He was buried in Joplin, Missouri 2.

Legacy and Impact on Law Enforcement

While it is often claimed that Underhill was the first criminal killed in a shootout with FBI agents, historical records suggest this may not be accurate. However, his case remains one of the earliest and most publicized instances where the Bureau deployed coordinated, armed operations to eliminate a dangerous fugitive. The tactics used in the Shawnee ambush—surveillance, intelligence gathering, multi-agency coordination, and precise force deployment—set a precedent for future FBI operations 3.

J. Edgar Hoover, then head of the FBI, closely monitored the case. He reportedly viewed Underhill as a major threat and took personal interest in his capture 1. The operation against Underhill demonstrated the FBI’s capacity to act as a national strike force, a capability that would be refined in subsequent years during the pursuit of outlaws like John Dillinger and Pretty Boy Floyd.

Underhill’s death also sparked retaliation. His remaining gang members, led by Ford Bradshaw, attacked the town of Vian, Oklahoma, in a violent rampage intended as revenge. However, without Underhill’s leadership, the gang quickly disintegrated. Within months, most were either killed or apprehended, marking the end of the Bailey-Underhill Gang’s reign 1.

Media of the time widely covered Underhill’s exploits, dubbing him the “Tri-State Terror” due to his crimes in Oklahoma, Kansas, and Arkansas. His case was later featured in the radio series Gang Busters, part of the Phillips H. Lord Collection preserved by the Library of Congress, ensuring his story reached new audiences in the 1930s and beyond 6.

Ron Morgan’s book The Tri-State Terror: The Life and Crimes of Wilbur Underhill provides a comprehensive account of his criminal career, drawing from surviving documents and newspaper reports 4. Similarly, Michael Newton’s Encyclopedia of Robberies, Heists, and Capers highlights Underhill as a pivotal figure in the era of outlaw bank robbers 1.

Conclusion

Wilbur “Mad Dog” Underhill’s life was one of perpetual defiance. Born into a world shaped by crime, he escalated from petty theft to murder, from short prison terms to multiple life sentences, and from regional nuisance to national menace. His ability to escape custody time and again, combined with his ruthlessness in executing both crimes and killings, made him a feared and legendary outlaw.

His final confrontation in Shawnee was not just the end of a criminal career, but a symbolic moment in the evolution of federal law enforcement. The FBI’s successful operation against him signaled a new era—one where outlaws could no longer expect sanctuary, and where federal power could be projected with deadly efficiency.

Today, Underhill is remembered not only for his violence, but for the questions his life raises: about justice, rehabilitation, public safety, and the thin line between man and myth. He remains a haunting figure of the Depression-era outlaw boom, a reminder that even the most cunning fugitives cannot outrun justice forever.

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Picher Theater Robbery & Murder

Grave of Earl O’Neal

Killing of Wichita patrolman Merle Colver (August 13, 1931)

 On his crime spree with nephew Frank Underhill, he shot Patrolman Colver three times in the head, killing him instantly; a 2‑year‑old child was also killed in crossfire; earned a second life sentence

2 year old Jack Myles