August 25, 1896
On this day, the Houdini bandit, Bill Doolin, finally failed to escape the grim reaper.Bandit extraordinaire, he’d evaded the law for nearly a decade, slipping from the grip of lawmen numerous times.
While most sources agree on the 25th, some say Doolin (left) may have actually died a day earlier. It’s fairly certain, however, that he was born on a farm in Arkansas in 1858. Drifting into Oklahoma at 23, he worked for 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 at the same time.
Doolin was a gifted cowboy and good with a gun. But by the early 1890s he was supplementing ranch hand wages with other people’s money, participating in a number of bank robberies and train hold-ups, sometimes with the Dalton gang. Their association was short-lived, however, and so were some of the Daltons.
In a classic outlaw over-reach, in 1892 the Daltons attempted to stick up two banks simultaneously resulting in a shoot-out that killed Bob (above) and Grat Dalton (left) along with Bill Powers and Dick Broadwell.
Depending on whose story you believe, Doolin missed the deadly shoot-out because 1) his horse went lame, 2) he’d argued with the Daltons over proceeds from another robbery 
or 3) he was in an alley holding the get-away horses.
A third Dalton, Frank, (right) also met an untimely death in a confrontation with a posse in November of 1887. Left to his own devices Doolin then founded the Wild Bunch in 1892. Not to be confused with Butch and Sundance, they were known locally as the “Oklahombres.” Ironically the next year he married a preacher’s daughter, Edith Maria 
Ellsworth, (below) in a secret ceremony and held up a train on his wedding day.
Until 1896 Doolin and company robbed banks, sacked trains and stuck up stages, at one point getting away with a $40,000 haul from an east Texas bank, amounting to as much as $1 million today.
With pressure increasing to bring them to heel, the Wild Bunch continued to evade posses and foil ambushes, possibly with the help of two teenage bad 
girls, Jennie Stevenson, a.k.a. Little Britches and her sidekick, Anna Emmeline McCoulet, Cattle Annie. (Left, Little Britches and Cattle Annie)
Finally Doolin was captured by legendary lawman, U.S. Marshal Bill Tilghman in 1895. While awaiting trial he masterminded a mass jailbreak, taking 37 prisoners with him.
Perhaps smarting from the humiliating escape, Tilghman enlisted the help of two other famous marshals, Heck Thomas and Chris Madsen. Dubbed “The Guardians,” the crime-fighting trio gets credit for capturing or killing 300 outlaws in the late 1800s.
Lawmen Tilghman, Thomas and Madsen
After slipping through Tilghman’s clutches, some sources say Doolin went to Mexico and was killed by Heck Thomas near Lawton, Oklahoma. In this version of his demise, he had returned to his father-in-law’s farmhouse to collect his wife and child. Others speculate that he was actually killed by Thomas in Mexico instead.
The first scenario is the most likely, according to a number of sources. Doolin is for a fact buried in boot hill at Guthrie, Oklahoma, next to fellow train robber, Elmer McCurdy. He was 38.
By 1898 nearly all of Doolin’s Wild Bunch had also been killed. Little Britches 
and Cattle Annie were both serving two year sentences in the reformatory in Framington, Massachusetts. Little Britches then falls off history’s radar after her brief ride on the wild side. Cohort Cattle Annie 1) died of tuberculosis in New York City shortly after her release from Framington or 2) she married, had two children and lived happily ever after.
A fourth Dalton, Bill, (above) joined the Doolan gang and lasted until 1893 when he too was shot and killed by a posse. The only Dalton to survive the Wild West was Emmett. (Below) Shot 23 times and given a life sentence, he served 14 years in 
prison in Lansing, Kansas, and was eventually pardoned. He moved to California, becoming a realtor and, what else, an actor. He died in 1937 at 66.
Doolin’s three nemeses, Tilghman, Thomas and Madsen, all remained in law enforcement of one kind or another. 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.
The Dalton Gang Hideout and Museum, 502 Pearlette Street, Meade, Kansas, is the former home of Eva Dalton Whipple, sister to all those wild Dalton brothers, she married John Whipple, owner of a general store in Meade. The Whipple’s lost the house in 1892 and it was sold to H. G. Marshall, who discovered a tunnel leading from a closet in the house to the barn. The house was restored in 1941 as part of a Works Progress Administration Project.
A book on Eva Dalton Whipple and her infamous brothers is available in the Hideout gift shop. Open 9 to 5, Monday through Saturday and Sunday, 1 to 5, and RV parking is available. Admission is $5. For more information go to oldmeandecounty.com/hideout.
© Text Only – 2019 – Headin’ West LLC – All photos – public domain or fair use.
*Head On West strives for historic accuracy and uses a number of sources considered reliable. When research differs on significant facts, the various points of view will be cited.