This monument to the bloody event known as the Young brother’s massacre stands in Springfield, Missouri near Route 66. Photo Jax Welborn

In the era of Route 66 renaissance where the old road is occasionally viewed as America’s longest theme park there is often a myopic view that centers on neon lit nights, tail fins, and the era of I Like Ike buttons. It is easy to forget that this now quiet highway was once a transportation corridor traveled by tens of thousands of vehicles every day. Today the road may be a string of living, breathing time capsules, a destination for tens of thousands of international Route 66 enthusiasts seeking the romanticized image of an authentic American experience but before being replaced by the interstate highway system it was an artery of commerce, legal and illicit. It was traveled by vagabonds and vagrants, vacationing families and serial killers, hitchhikers and truck drivers, movie stars and murderers, escaped convicts and people simply seeking a better life in the promised land that was sunny California.

It was known as bloody 66, and not just because of the staggering number of traffic fatalities. From its inception in 1926, U.S. 66 served as the backdrop for countless headline grabbing tragedies, murders, disasters, and industrial accidents.

Even though Nat King Cole crooned about getting your kicks on Route 66, and Todd and Buzz cruised it in search of adventure every week, and Lucy and Desi followed it west to California in a series of comedic episodes on their popular television program, the highway had a dark side. Route 66 was marketed as the Main Street of America for more than five decades, but in the shadows of main street, death often lurked. Route 66 today is often viewed in the context of being a 2,000-mile adventure, America’s longest attraction. It is easy to forget that the charming little villages and towns along Route 66 that seem as though they are settings from Norman Rockwell prints were often the scene of tragedy, of murder, of mayhem, and of dark deeds.

That was how I opened the book Murder & Mayhem on The Main Street of America: Tales from Bloody 66 written for Rio Nuevo Publishing. Even an astute student of history can have a distorted view of the past. This is especially true when a person gets caught up in the magic of Route 66 in the era of renaissance.

Courtesy of the Minnesota Historical Society

The truth is that Route 66 was one of the nations most popular highways. It was the primary route of choice from travelers headed for California from the Midwest, or to the Midwest from California. So, it should come as no surprise to learn that it was a favored hunting ground of serial killers. And it was the great escape for fugitives from the law.

In the 1920s, counted among the most prolific and most violent graduates of Tulsa’s Central Park school of strong arm artists, murderers, thieves, extortionists, burglars, and pick pockets was Ray Terrill, the Kimes brothers, George and Matthew, “Creepy” Alvin Karpis, and Fred Barker.

Terrill’s first attempt at bank robbery ended with a conviction for second degree burglary and a sentence of two years in the state prison. Using the alias “G.R. Patton”, Terrill had partnered with Arthur Baker to rob a bank in Muskogee, Oklahoma on January 15, 1921, but they were caught in the act.

Within days of his release on March 1, 1923, Terrill teamed up with Al Spencer, an associate from the Central Park days who was running a gang of bank robbers. On March 26, in Mannford, Oklahoma a robbery went awry, and two people were killed during the firefight and getaway that became a running gun battle. Then on August 20, 1923, Terrill, members of Spencer’s gang, and Frank Nash stole an estimated $20,000 in cash and bonds from the Katy Limited near Okesa, Oklahoma. This was the last recorded train robbery in the state’s history.

After Spencer was killed in a shoot out with police, Terrill formed his own gang with Herman Barker, Wilbur Underhill, and Elmer H. Inman. In brazen after hours burglaries, the gang hit banks and stores, stole safes, and cut them open at Herman Barker’s hide out at Radium Springs Health Resort near Salina, Oklahoma.  The gang operated with impunity until Terrill and Inman were arrested for burglary in Ardmore, Oklahoma in 1926. They each drew a sentence of five years but escaped together on September 27, 1926. Terrill immediately began putting a gang together.

George and Matthew Kimes robbed their first bank in Depew, Oklahoma (the first community that was bypassed in a Route 66 realignment) on June 30, 1926. Matt had escaped from the jail in Bristow the day prior. Then on August 20, they stole an estimated $5,000 from a bank in Beggs, Oklahoma and, a few days later, led a gang that raided two banks in Covington simultaneously.

A bank robbery attempt in Sallisaw culminated in a running gun battle with police. Deputy Perry Chuculate was killed, and two hostages were taken as the gangsters fled toward Arkansas. The next day near Rudy, at the home of a cousin, Ben Pixley, the wounded brothers surrendered to police and were jailed in Sallisaw to await trial. George received a sentence of 25 years for bank robbery and was sent to McAlester state penitentiary. For the death of police officer Perry Chuculate, Matthew was given a sentence of 30 years .

Then Terrill led a daring raid on the Sallisaw jail with Herman Barker and Elmer Inman on November 21, 1926 and freed Matthew Kimes. The newly formed gang launched a crime spree along Route 66 in several states. In Sapulpa, Oklahoma on January 10, 1927, they robbed the bank of more than $42,000. A week later Herman Barker, Elmer Inman and Matthew Kimes were caught in the act of burglarizing a bank in Joplin, Missouri. During the high-speed chase that ensued, Kimes escaped into Kansas on Route 66. Terrill and Barker made it to a safe house in Carterville but were surrounded by police a short time later. In the shootout that followed Barker and Terrill surrendered.

Terrill was being returned to prison in McAlester when, on January 19, he escaped from custody.  A few days later, he rejoined Mathew Kimes, and the duo launched another crime spree. On May 27, Terrill was identified in a daring daylight bank robbery in McCune, Kansas in which more than $200,000 was taken. Two days later, Kimes and Terrill returned to Beggs, Oklahoma with nine gunmen and robbed two banks. The escape became a running gun battle and Marshal W.J. McAnally died in the street from multiple gunshot wounds.

Terrill and Inman fled east, and were arrested in Hot Springs, Arkansas on November 26, 1927. In June of 1927, Blackie Wilson, a Kimes gang member arrested during a robbery, in the hope of leniency, confessed to numerous crimes and provided details on gang members.

Meanwhile Matt Kimes and Raymond Doolin fled west. Would you care to guess what highway they followed?

If your a fan of true crime stories, Route 66, and tales of the ruthless gangsters that stalked the highways of America during the Great Depression, I have a book to suggest. Murder & Mayhem on The Main Street of America: Tales From Bloody 66. And if you order it direct from me, I can deface it with an autograph.

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