The Good, The Bad, and the Incredibly Stupid

The Good

William Halsell migrated to Texas from Alabama somewhere around 1870.  His wife Mary was of Cherokee ancestry.  In Texas, William ended up working for his brother-in-law, Dan Waggoner, on the Triple D Ranch.  With his brother Glenn, William drove a herd from the Triple D up the Chisolm Trail into the Indian Territory.  William turned the herd at the Cimarron River, followed it to the Arkansas River, and then moved up the Verdigris River to Vinita.  This “less traveled” route was later called the Halsell Branch of the Chisolm Trail.

While awaiting the Cherokee’s permission to drive cattle through their land, William made friends with Dennis Bushyhead, who later became a principal chief of the Cherokee Nation.  In 1877, William and his brother Glenn leased land along the Cimarron River and built a ranch five miles northeast of present-day Guthrie.  In 1881, William and Glenn dissolved their partnership and sold their spread for around $340,000.  William capitalized on his wife’s Cherokee lineage and moved his ranching operation into the Cherokee Nation.  William was adopted into the tribe, made Vinita his home, and started up a new ranch along Bird Creek, 8 miles north of Tulsa.  He adopted the “Mash O” brand and increased his herd (and fortune) by purchasing South Texas cattle, driving them to Oklahoma, fattening them in the summer and fall, and then selling them before winter.  In this way, he avoided losing livestock in Oklahoma’s harsh winters and winter droughts.

Eventually, William turned Mash O operations over to his son Ewing while he invested in real estate and started banking partnerships, all of which increased his wealth.

The Bad

One of the young cowmen working on the Halsell ranch was Richard West.  We don’t know much about Dick West.  He may have been born in 1865, and according to legend, when Dick was about 3 or 4 years old, Texas settlers discovered him wandering in the south Texas scrub, adopted him, and raised him as their own.

Richard probably had a typical life in South Texas.  He learned how to sit a horse, drive cattle, and roping.  These were skills that led to his work as a cowhand and trail driver.  He eventually found his way to Oklahoma, where he worked on the Mash O, and from every account, West was a competent, reliable cowman.  Oklahoma was where Dick West met the gunman named Bill Doolin.  In 1892, West joined the Dalton-Doolin Gang, also known as the “Wild Bunch.”

Dick West was riding with Doolin when the gang robbed the bank in Southwest City, Missouri.  The robbery started okay, but as the outlaws mounted their horses, armed citizens converged on the band, blocking their way out of town.  Outlaws were shooting at everyone, in every direction.  Two curious citizens went into the street to find out what was going on, and Dick West shot them.  West was also wounded in the fight.

After assisting Doolin in a train hold-up, West followed the outlaw into New Mexico and resumed a cowman’s life.  Doolin returned to Oklahoma, where lawmen killed him in 1896.  In 1897, West returned to Oklahoma and helped form the Jennings Gang, which might have been the biggest collection of morons in old west history.

Meanwhile, the Four Guardsmen[1], having killed Bill Doolin, began looking for other Doolin gang members.  In Guthrie, an informer told Tilghman and Thomas about a suspicious person living in a dugout nearby.  Tilghman recognized the description of the person’s horse as one belonging to Dick West.  Forming a posse of six, Tilghman began looking for West the next morning, Wednesday, 13 April.  Thomas spotted a man walking through the woods at about the same time as West saw Thomas; West turned around and ran to his horse.  For Dick West, it may as well have been Friday; he didn’t make it to his horse.

Richard West, who stood only 5’1” tall, was generally referred to as “Little Dick” West.  His wild-eyed appearance gave some people the impression that Dick was a few bubbles off plumb: he was unpredictable, dangerous, and very cunning.  Town folks buried West’s smaller-than-normal casket near the remains of Bill Doolin.

The Incredibly Stupid

Alphonso J. Jennings (1863-1961) was an attorney, an outlaw, a movie actor, and a politician.  He and his brothers relocated to Oklahoma from Virginia around 1890.  He initially served as the Canadian County prosecuting attorney from 1892-94 and then joined his brothers, Ed, and John, in a law practice in Woodward.  At the time, Ed and John were engaged in a court case that involved rival attorney Temple Houston[2]. Here’s what happened:

According to a news article in the Woodward News, Ed Jennings questioned the admissibility of a witness’s testimony, which prompted Houston to suggest that Jennings was “grossly ignorant of the law.” Jennings then attempted to slap Houston for his remark, and the two men drew their firearms inside the courtroom.  Court officials stepped in to prevent gunplay, and the judge adjourned the court until the following day.

At around 10 that night, Ed, and John confronted Houston and his friend Jack Love at Garvey’s Saloon.  Gunsmoke followed the exchange of angry words, and Ed Jennings lay dead on the floor, blood flowing from a head wound.  According to the testimony of Walter Younger, an employee of the Woodward News, with Ed lying dead on the floor of the saloon, John Jennings left the saloon and went looking for a gun.  John Jennings subsequently re-entered the saloon and was shot, sustaining a severe wound to his arm that left him crippled for the rest of his life.  Lawmen arrested Houston and Love, charging them with manslaughter, but the court released both men on bail.  Today, there is no record of the trial.  All we know is that a jury acquitted Houston and Love of the charges against them.

After the acquittal of Houston and Love, Al Jennings left Woodward.  For a while, Al Jennings became a drifter, finding occasional work as a ranch hand in the Creek Nation.  Counted among his cowboy friends was a fellow everyone called “Little Dick” West.  West helped Jennings form an outlaw gang.  In the annals of the old west, the Jennings Gang was remarkable for only one thing: they bungled nearly every outlawry attempt.  Gang members included Al Jennings, his crippled-for-life brother, John, Dick West, and Morris and Pat O’Malley; they became the scourge of defenseless general stores.  They tried to rob a post office once, but the fellows inside were armed.  Gang-members then turned their attention to trains.

On 16 August 1897, the Jennings Gang robbed the passenger train a few miles south of Edmond, Oklahoma.  The Edmond robbery would have been a great haul were it not for the fact that in laying dynamite to blow open the Wells-Fargo safe, Little Dick instead managed to blow up the entire train car.  When the debris and dust cleared, the safe was still sitting where it previously stood, locked and unscathed.

Their second attempt was more productive.  Little Dick managed to break into the safe, but they only netted a few hundred dollars.  They robbed one passenger of his bottle of whiskey, and they found a bunch of bananas, too—so the effort wasn’t entirely wasted.  It was after this incident when Dick West left the gang.  He may have reasoned that he could do better on a street corner with a monkey and an accordion.

The gang’s third train robbery was much more profitable —$ 30,000 in cash and the full attention of federal Judge Isaac Parker and his United States Marshals.

Whenever Al Jennings, Esq., wasn’t robbing trains, he was hiding out in the Snake Creek vicinity in the Indian Territory.  On 30 November 1897, deputy U.S. Marshals shot and wounded Al Jennings.  Al managed to escape while recovering from his wounds, but he was recaptured a week later and escorted to Judge Parker’s courtroom.

Judge Isaac Parker probably had a sense of humor, but it was lost on Al Jennings if he did.  Parker sentenced Jennings to life in prison.  With the assistance of John, Al Jennings promptly appealed his conviction to a higher court.  In 1902, an appellate court overturned Jennings’ conviction, and two years after that, President Theodore Roosevelt granted Jennings a pardon[3].

In 1905, Al Jennings was looking for a third (less exciting) career when he sent O. Henry[4] a story he wrote about his life’s adventures.  He titled it, Holding up a Train.  From every account, the story was popular and widely distributed.  His celebrity led Al Jennings to three movie producers named Bill Tilghman, Chris Madsen, and E. D. Nix.  In films and in Jennings’s mind, he was a Robin Hood type character fighting for justice.  He did this, apparently, by robbing Mom & Pop general stores and train passengers.  By 1912, Jennings had convinced himself that he had what it takes to enter the political arena, and if we judge him by our present-day standard, indeed, he did.  Running for governor of Oklahoma, Jennings finished in third place in a six-man race.  Jennings subsequently moved to California, where he continued his movie acting career.  Jennings died in 1961; he was 98 years old.

Al Jennings —the dumbest outlaw in Oklahoma history “made it” in Hollywood.


  1. “Al Jennings, the People’s Choice,” Chronicles of Oklahoma, Duan Gauge, Autumn 1968.
  2. Patterson, R. M. Train Robbery: The Birth, Flowering, and Decline of a Notorious Western Enterprise.  Boulder: Johnson Press, 1981.
  3. Scales, J. R., and Denny Goble. Oklahoma Politics: A History.  Norman: University of Oklahoma Press, 1982.
  4. Shirley, G.  West of Hell’s Fringe: Crime, Criminals, and the Federal Peace Officer in Oklahoma Territory, 1889-1907.  Norman: University of Oklahoma Press, 1980.


[1] Bill Tilghman, Heck Thomas, Chris Madsen, and Bud Ledbetter.

[2] Temple Houston was a dangerous man to provoke.  From around the age of 13, he worked as a cowhand.  He later worked on a riverboat, but we do not know how he earned a living on the river.  Temple also served as a page in the U. S. Senate, attended Texas A&M University, and studied the law at Baylor College, finishing first in his class.  He was (at the time), the youngest attorney to open a law practice in Texas.  He also served as a district attorney in Texas.  Temple Houston never went anywhere without his hog leg, which he called “Old Betsey.”  Temple Houston stood more than six feet tall, could quote the Bible, and was known as being among the best pistol shots in the entire west.  The Jennings brothers could scarcely have picked a worse man to pick a fight with.  Temple was the son of Sam Houston.

[3] President Theodore Roosevelt granted three (3) pardons while in office.  The first to Sevillano Aquino, a Philippine general sentenced to death in 1902 for anti-American activities, Stephen A. Douglas Puter, convicted of land fraud in 1906, pardoned in exchange for turning state’s evidence, and Al Jennings, whose conviction was overturned on a technicality.

[4] O. Henry was the nom de plume of William Sydney Porter (1862-1910), a short story writer known for his surprise endings and witty narration.

About Mustang

Retired Marine, historian, writer.
This entry was posted in History, Oklahoma, Society. Bookmark the permalink.

4 Responses to The Good, The Bad, and the Incredibly Stupid

  1. kidme37 says:

    Yea, Jennings would make a heck of a politician today if only he had a larger criminal history.

    Liked by 3 people

  2. Andy says:

    Outrageously funny. Jennings proved that crime doesn’t always pay.

    Liked by 1 person

    • Mustang says:

      I suppose most of the old west outlaws were dumb as a box of rocks, but that didn’t make them less dangerous. Yeah, Jenning’s story made me laugh, too. Thanks, Andy.

      Liked by 1 person

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