Trail Dust - August 25

On this day in 1896, the outlaw Bill Doolin may or may not have been shot and killed in Lawton, Oklahoma.

Some sources say the event actually took place on August 24, but most report it as August 25.

Doolin, bandit extrordinaire and Houdini escape artist, evaded the law for nearly a decade and slipped from the grip of lawmen numerous times.

Born on a farm in Arkansas in 1858, Doolin drifted into Oklahoma in 1881 and worked as a ranch hand at the H-X Ranch owned by Oscar D. Haskall. It was there he apparently ran into bad company. Several of the Dalton brothers also worked on the H-X spread now and then.

He was a gifted cowboy and good with a gun. By at least the early 1890s Doolin was supplementing his ranch hand’s wages with other people’s money, participating in a number of bank and train robberies, sometimes with the Dalton gang. But their association was short lived and so were some of the Daltons.

In an 1892 criminal over-reach, the Daltons attempted to rob two banks simultaneously, resulting in a shoot-out that killed two of the Dalton brothers, Bob and Grat and two other gang members, Bill Powers and Dick Broadwell.

Depending on whose version you believe, Doolin missed the shoot-out because one) his horse went lame, two) he’d argued with the Daltons over the proceeds from an earlier robbery or three) he was there but was in an alley holding the get-away horses.

After the virtual demise of the Dalton gang, Doolin founded the cinamatic Wild Bunch in 1892 known locally as the “Oklahombres.” Ironically the next year he married a preacher’s daughter. Until 1896 Doolin and company robbed banks, sacked trains and stuck up stage coaches, at one point getting away with a $40,000 haul (about $1 million in today’s money) from an east Texas bank.

Pressure increased to bring the Wild Bunch to heal, but they continued to evade posses and foil ambushes possibly with the help of two teenage girls, Jennie Stevenson, a.k.a. Little Britches and her sidekick, Anna Emmaline McCoulet, Cattle Annie. Legendary lawman, U.S. Marshal Bill Tilghman managed to capture Doolin in 1895 but Doolin masterminded a mass jailbreak while awaiting trial, taking 37 prisoners with him in his flight to freedom.

Perhaps smarting from the Doolin escape, Tilghman enlisted the help of two other famous marshals, Heck Thomas and Chris Maden. This crime-fighting trio dubbed “The Guardians” is credited with capturing or killing 300 outlaws in the late 1800s.

Following his escape from Tilghman, some sources say Doolin went to Mexico and was killed by Thomas near Lawton, Oklahoma, after returning to his father-in-law’s farmhouse to collect his wife and child. Other sources say he was killed by Thomas in Mexico.

The former scenario is most probably correct since Doolin is for a fact buried in boot hill at Guthrie, Oklahoma, next to fellow train robber Elmer McCurdy. He was 38 at the time of his death.

By 1898 all of the Wild Bunch were dead. Little Britches and Cattle Annie got sentenced to two years in the reformatory in Framington, Massachusetts. Little Britches falls off history’s radar after her brief time the wild side and Cattle Annie either died of tuberculosis in New York City shortly after her release or she married, had two children and lived happily ever after.

Heck Thomas went on to become Lawton’s first police chief. He died there in 1912. Tilghman was shot by a corrupt prohibition officer in 1924 while serving as police chief of Cromwell, Oklahoma and Madden became an investigator for the governor of Oklahoma after serving as police chief of Oklahoma City. He died in Guthrie in 1944.