The Great Edmond Train Robbery

Written by David A. Farris in the February 2010 Issue
Edmond’s brush with outlaw infamy occurred August 16, 1897 shortly before midnight, when the Jennings Gang robbed a southbound Santa Fe passenger train, about a mile south of downtown. During this period of pre-statehood history, daring outlaw gangs often became legendary in Oklahoma Territory. The Jennings Gang become legendary, but oddly enough, it was for their incompetence. Their Edmond job was no exception.  

Just two years earlier, Al Jennings and his older brothers, John and Ed, were attorneys in good standing, residing near Woodward. They had proudly followed in the footsteps of their father, Judge J.D.F. Jennings. John and Ed were hired to represent some young cowboys accused of stealing a keg of beer from a Santa Fe railroad car.

Attorney for the prosecution was Temple Houston, the fiery and charismatic son of Texas founder Sam Houston. Despite the fact that these were men of education and refinement, they were also not beyond the use of violence to resolve their differences.  

On October 8, 1895, the contention between both councils in court resulted in all three men drawing their pistols. Fortunately, cooler headed members of the court subdued them before any shots were fired.

Their feud resumed later that evening when the brothers entered the Cabinet Saloon to find Houston accompanied by former sheriff Jack Love. After further words the men pulled their pistols and a short, dodging gun battle commenced. Ed was killed instantly. John, shot through his body and one arm, managed to run out of the saloon and up the street about 200 yards before he collapsed.

The Jennings had been way outmatched by opponents who remained unscathed except for a few bullets that had torn through their clothing. John survived, and Houston and Love were ordered to stand trial. Not only were both men acquitted, but it was further decided that Ed had drawn first and the round that struck him in the temple killing him must have been fired from his brother’s gun.  

Al telegraphed another older brother Frank, in Colorado, to come join him in a revenge plot against the two men. To the old Judge’s disappointment, he watched two of his boys ride off on their dubious mission. Whether Al lost his nerve to face such experienced gunmen or got side tracked playing outlaw, he wisely abandoned his revenge plans and tried his hand robbing trains.

He recruited hard cases he met along the outlaw trail to form a gang. Pat and Morris O’Malley, a couple of tough, Irish brothers were a welcome addition to the Jennings’ Criminal Enterprise, but the gang was lacking any real outlaws. This was remedied when two former members of the Doolin Gang, Little Dick West and Dynamite Dick Clifton agreed to throw in.

The train left the Edmond station for Oklahoma City after a scheduled stop for water. When it reached a pre-arranged spot, three masked men climbed over the “tender” from the “baggage blind” into the cab where the engineer was ordered to stop the train.

Four men sprang from the tall grass alongside the tracks bursting into the express car where the safe was waiting; now all they had to do was get it open. In the meantime, the bandits kept the passengers huddled in their seats by firing shots just over their heads. Two attempts were made to blow open the safe using dynamite, but amazingly the sturdy Wells Fargo remained intact. In frustration, the gang turned to the passengers, taking what loot they could before disappearing into the night.  

When the train finally arrived in Oklahoma City, the conductor notified the sheriff’s office who then alerted U.S. deputy marshal Heck Thomas in Guthrie. At dawn, both posses met at the crime scene and were soon hot on the gang’s trail.
Not long after, further disappointments caused the gang to become disillusioned and they dispersed. However, the lawmen were still in pursuit. The Jennings and O’Malleys were soon under arrest and on their way to prison. The two Dicks were both killed in separate shootouts while resisting arrest.

When Al was released from prison he moved to Hollywood, California where he worked as a technical adviser on Western movies. He also wrote a greatly embellished book about his outlaw days, which was later made into a movie under the same title of Beating Back.

Al Jennings and his gang may have missed the outlaw glory they sought in Edmond. Instead of legendary men of infamy, they became a source of lighthearted entertainment. However, they became a part of the colorful and exciting past that is Sooner State history that will last for generations.
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