7/14/1892 - Seeking funds to use to escape American law enforcement by relocating south to Mexico, the Dalton Gang (a rogue's gallery of pistoleros and thieves consisting of 23-year-old Bob, 31-year-old Grat, and 21-year-old Emmett Dalton, 34-year-old Bill Doolin, 26-year-old George "Bittercreek" Newcomb <so named for continually singing a popular cowboy ditty, "I'm a wild wolf from Bitter Creek and it's my night to howl!">, 26-year-old Charley Pierce (Newcomb's best friend), Dick Broadwell of Hutchinson, Kansas, and former Bar X Bar Ranch cowboy Bill Powers) rob a northbound Missouri, Kansas & Texas Railroad train at the town of Adair, Oklahoma (in the northeastern part of the state, not far from Oklahoma's borders with Kansas, Missouri, and Arkansas).
Robert Rennick "Bob" Dalton
Planned while hiding out after their Red Rock robbery of a Santa Fe Railroad train at the Dunn Farm near Ingalls, Oklahoma (the place where the Dunn Brothers will betray and kill their former friends, Bittercreek Newcomb and Charley Pierce over a money dispute, and the affections of the Dunn's sister, Rose), lawmen learn of the raid and plan to ambush the gang by loading the train with a dozen gunmen interested in the rewards for various members of the band.
Totally confident in their abilities, the gang arrives at Adair at around 9:00 in the evening and immediately goes to business by holding up the local railroad agent and ransacking the station for cash and valuables, then calmly selecting comfortable seats around the station, cradling their Winchester rifles, await the 9:42 coming of passenger train #2.
Jumping into action when the train pulls into the station, Emmett and Grat Dalton swing themselves into the engine cab and cover its occupants, Powers, Broadwell, and Bob Dalton position themselves on the train platform in front of the door to express car, and Doolin, Bittercreek, and Pierce set up to persuade anyone in the passenger cars from interfering in the robbery ... which does indeed happen moments later!
Realizing the train is being robbed, Marshal Sid Johnson of Muskogee (a former friend of Bob Dalton's when they served as peace officers for Judge Parker in Fort Smith, Arkansas), Indian Police Chief Charley LeFlore, and railroad detective J.J. Kinnet grab their rifles, jump off the train, take firing positions behind a coal shed, and open up on the gang. Unfortunately for the cause of law and order, the other ten men in the posse decide that risking life and limb against the gang of desperadoes is a fool's game when confronted by the actual outlaws, and hide in the darkened train, firing only occasionally at the shadows on the train platform. And maybe wisely so, for the outlaws start immediately blasting away at the coal shed and soon silence the trio of lawmen there ... Kinnet takes a slug in his right shoulder, Johnson suffers a painful flesh wound, and LeFlore has the stock of his weapon hit and is put out of action by his hands being filled with splinters.
Covering the Engineer!
Opposition quieted for the moment, the outlaws break into the express car and find the agent inside, a man named Williams, reluctant to open the train's safe, claiming he doesn't know the combination. A lie, as if he knows Hollywood will one day make movies about the gunslingers of the Old West, Bob Dalton convinces the man to open the safe by drawing his pistol and snapping off a shot at the agent's head that comes within less than a inch of being brain dead fatal. Presto, the safe is opened and the gang rides out of town $40,000 richer than they were earlier in the evening (but not enough for Mexico, causing Bob Dalton to decide one more robbery is necessary ... a job that will best Jesse James and show the town he grew up in that he can't be looked down at any more ... the gang will take the two banks of Coffeyville, Kansas at the same time).
Gang gone, robbery complete in less than 15 minutes, the unfortunate evening is however not over for the town of Adair. Playing cards at the local drugstore, 65 yards away from the railroad station, Dr. W. L. Goff and Dr. T.S. Youngblood are both hit by stray bullets from the short fight between the outlaws and the trio of fighting lawmen ... Youngblood is hit in the right foot (a wound that will cause part of the foot to have to be amputated), while Goff is struck in the thigh, a bullet that severs the physician's femoral artery and causes him to bleed to death before help can arrive.
A clean getaway from Adair, but not from reaping what they have all sown leading outlaw lives ... Bob Dalton, Grat Dalton, Dick Broadwell, and Dick Powers will all perish in a Coffeyville alley, Emmett Dalton will be wounded 23 times at Coffeyville and receive a life sentence for his actions there (he will serve 14 years before being pardoned), Bittercreek and Pierce perish at the hand's of the reward seeking Dunn Brothers, and Doolin will be riddled by buckshot when he refuses to surrender as he is about to leave for Mexico with his wife and child from his in-law's farm outside of Lawson, Oklahoma.
Powers, Bob Dalton, Grat Dalton, and Broadwell - October, 1892
Wounded Emmett - October, 1892
Newcomb & Pierce - May, 1895
Doolin - August, 1896
7/24/1892 - just another violent day in the Indian Territory!