Jimmy Overstreet, the dapper youth bandit was arraigned on December 20, 1924, on the charges of robbing the Federal National Bank. He was charged under a new law that set the minimum of 25 years imprisonment, up to the death sentence in the electric chair.


Jimmy Overstreet, the dapper youth bandit was arraigned on December 20, 1924, on the charges of robbing the Federal National Bank. He was charged under a new law that set the minimum of 25 years imprisonment, up to the death sentence in the electric chair.

The officers were not taking any chance of losing him, not allowing any loungers, loafers, or visitors in his area of the jail.

“We are taking no chances,” said Night Chief Corliss Howell, “Jimmy is desperate and is a member of a daring gang of vicious looters.”


“The Swell Kid,” also known as the “Jelly Bean Desperado,” bandit and suspected killer, said he would swap out with the law and tell all. The deal was to let his wife, Bobby Livingston, the “flapper bandit,” have her liberty. Even though she was considered as a “stool pigeon” in giving out the information on the robbery and Overstreet. He clearly held no grudge against her.

The two, along with murdered bandit Joseph Marshall’s wife, Helen Cardwell, were questioned for three hours on December 22, by County Attorney Claude Hendon, Sheriff Grover Butler, and Chief of Police L.A. Brown.

The Shawnee youth, whose career in crime began in childhood, when he was the leader of the “dirty dozen.” He led a group of youthful desperadoes. He did not claim to be innocence in all of the events. However, until a deal was made, he did not maintain his guilt.

Hendon declared that the youth had been the companion of millionaires, who had tipped waitresses $10, and caddies $5, when he was captured at one of the most fashionable hotels in Texas. He was attired in an expensive silk and wool golf outfit and showed no signs of mental stress following a severe grilling. However, there was a demonstration of emotion when Jimmy and Bobby met.

Affectionately, the “Swell Kid” embraced the sobbing Bobby, who for the past week had pined for her “lost bandit love” in song. She filled the city bastille with love ballads.

Overstreet would “swap out,” provided an agreement between the law and the fallen robber was intimated by the county attorney. He said he would tell the entire story if Bobby was given her freedom. He also wanted only a sentence of 25 years for himself, and not death.

It was determined that Livingston would not be given her freedom, but her bond was reduced from $10,000 to $5,000. The county attorney said he would recommend to the court that she get a suspended sentence.

Overstreet waived the reading of the complaints filed against him when he was arraigned before Justice of the Peace Edwin Moore. His preliminary hearing was set for December 24. Both of his parents were present at the hearings. Only about 20 spectators attended the short session.


Jimmy Overstreet, the “Prince of Bandits,” confessed to bank robbery, and was sentenced to serve a term of 25 years in the state penitentiary at McAlester on the morning of December 24, 1924. He pled guilty to Judge Leander G. Pitman in superior court. There was no demonstration, with Jimmy calmly answering the court’s query, “Are you ready for your sentencing?”

The bond of his wife, Bobby Livingston, in the filling station robbery was reduced to $1,000.

By the next day, Jimmy and Bobby were preparing to say goodbye, maybe forever, when they met in the afternoon for a farewell party. County Attorney Claude Hendon granted their wish to spend Christmas afternoon together. Her cell was decorated with scarlet bells and angels.

Overstreet was starring in the face the possibility of 40 years behind bars. It was a 25-year sentence, the minimum provided for in the new statutes governing the robbery. He also had a 15-year sentence pending for an old crime.

With the disposition of the Overstreet case, there remained two bandits still at large. They were believed at the time to be Arthur Dixon and Charles Price. Price turned out to be Brice McConnell. Both were considered as East St. Louis gangsters.

Word also came that “Blackie” Thompson, falsely accused at first in the Shawnee robbery, had been captured by U.S. Marshall Alva McDonald and his forces near Bartlesville. To be arrested, he did not need the Shawnee heist on his resume, he had plenty of other crimes in which to “pay the piper” for.


Jimmy Overstreet left for the state prison at McAlester on the morning of December 27, to begin his 25-year prison term for the robbery of the Federal National Bank in Shawnee. This was just 17 days after the heist took place.

Bobby Livingston-Overstreet, the wife of the “Swell Kid,” visited him for the last time the day before. She had been released the day before after making her $1,000 bond. His parents and an uncle also visited his cell before his departure.

County Sheriff Grover Butler, deputy sheriffs Bill Deister and “Boots” Morris, along with City Detective Flavius Budd left with Overstreet on the 10 A.M. train to the east.

Jimmy, the dapper youth and desperado, who maintained a stoic countenance through most of the proceedings, displayed little emotion in bidding farewell to his parents and relatives. It was when he said goodbye to his wife that a slight demonstration of regret took place.

“Just forget all that has happened and try to correct and shape your future so you will find peace and happiness,” was his words to his 17-year-old wife Bobby.

“Dear Helen, I know it will be lonesome since my darling has left. But I will not worry for you are getting out and Helen, when I get out, if I were you I wouldn’t ever go to see “Timmie” or any of them or those on “State Street,” was his comment to Helen Cardwell-Marshall.

Four of the six gangsters from East St. Louis, who came south to show “Oklahoma tough boys a thing or two” had met disastrous fates.

(These stories and hundreds more appear in the first volume of Shawnee history, entitled: “REDBUD CITY: SHAWNEE, THE EARLY YEARS, 1830-1929.” It can be purchased by calling Clyde Wooldridge at (918) 470-3728, or by visiting the Pottawatomie County Historical Society at the old Santa Fe Depot. It can be purchased for $35. Volume two, “1930-1949,” is also available for $30. Volume three, “REDBUD CITY: SHAWNEE, THE MIDDLE YEARS, 1950-1969,” is now at the printer’s office and will be ready any day now. All three volumes are more than 400 pages with hundreds of photos and illustrations. Volume three is priced at $35. A combination of two or three can be purchased at $30 each. They are fully indexed, making it easy to look up individuals or places of business. Volume four 1970-1989, is scheduled for the fall of 2020; volume five 1990-2009, should be available in the fall of 2021; and volume six 2010-to the present, is scheduled for the fall of 2022. They are also available on thumb drive at the PCHS Museum. Volume Three, 1950-69 in thumb drive is currently available for purchase at Museum.)

Clyde Wooldridge is a local historian.