When Lawmen Turn : The Dalton Gang

The Dalton Gang’s start was in the Wild West, so named for the lawlessness of the untamed territories west of the Mississippi River – in the United States, during its frontier period.

The historical time period of the Wild West was right after the civil war, from 1865 – 1895, a period of thirty years or so.

It was famous for cowboys, native Indians, the lawmen, gunslingers, pioneers, prospectors, gamblers, scouts, and outlaws.

During this period, the score cards changed quickly, as lawmen turned outlaws, and outlaws turned lawmen.

It was also during this period, the Dalton Gang, rose to fame.

The gang was made up of the Dalton brothers who specialized in train and bank robberies.

Their father was James Lewis Dalton from Jackson County, Missouri.

He had served under General Zachary Taylor as a fifer for Company I, Second Regiment of Kentucky Foot Volunteers, during the Mexican War.

Dalton came west from Kentucky to Missouri during the late 1840’s and in the 1850’s, he was trading horses and running a saloon in Westport, Missouri (now Kansas City) when he married Adeline.

Adeline’s brother was the father of Bob Younger, Cole Younger and James Younger.

She was also related to gang members who rode with Jesse James

 

The Dalton boys, who formed the gang were born in quick succession: Frank (1859), Gratton “Grat” (1861), William M. “Bill” (1866), Bob (1869), and Emmett(1871).

Top Frank, Bob,Bill, Lower Grat , Emmett

In 1886, the Dalton’s  moved again to a place near Coffeyville, Kansas.

In this rough and wild area, the Dalton brothers inherited a tradition of violence on the bloody ground of the Missouri-Kansas border, where Quantrill’s Raiders and other guerrilla bands operated before and during the Civil War.

When the Oklahoma Territory opened for settlement in 1889, the family headed south again.

Most of their 15 children were born in Missouri before the family migrated .

The claim that James and Adeline Dalton chose was the SW ¼ of sec. 11, in town ship 17, north of Range 8, west of the Indian Meridan in Oklahoma.

This claim contained 160 acres, all bottom land, 6 miles north east of the town of King fisher, Oklahoma.

Times were hard in the new raw land. James Lewis Dalton, father of the clan, re turned to Kansas to work in Coffeyville while Mrs. Dalton remained on the claim with the children to prove it up.

However, James Lewis Dalton died along the way leaving Adaline to raise the younger children alone.

Adaline continued on, placing a claim on the banks of Kingfisher Creek in Indian Territory, where initially, she and the family lived in a dugout.

By this time the older Dalton brothers were on their own.

Lawmen

Frank Dalton was the one of the oldest brothers, and kept the others on their good behavior for some time, as they followed his model into the law.

He became a Deputy US Marshal, and his brothers rode with him in posses.

Frank Dalton was killed when he was tracking a horse thief in the Oklahoma Territory.

Dalton and another deputy marshal had located the fugitive with his companions on November 27, 1888, and tried to arrest him.

 

The outlaws resisted, and shot Dalton dead.

Two of the outlaws were killed, and Dalton’s companion was wounded.

The wanted horse thief, Dave Smith, escaped capture.

On December 3, the remaining outlaws were located and a second gunfight took place.

Deputy U.S. Marshal Ed Stokley shot and killed the horse thief, but was fatally wounded.

Shortly after, brothers Grat, Bob, and Emmett Dalton also became lawmen.

Grat Dalton, first taking his place as a Deputy Marshal in Fort Smith, Arkansas and two years later as a Deputy Marshal for the Muskogee court in Indian Territory in 1889.

That same year he received a bullet in his arm while attempting to arrest a suspect.

Bob Dalton was also commissioned as a Deputy Marshal for the federal court in Wichita, Kansas, working in the Osage Nation, in 1889.

Bob Dalton, who would later become the leader of the Dalton Gang, was the wildest of the bunch.

Frontier conditions for towns were often strained, and in 1890, after not being paid money owed them, the brothers became outlaws.

Bob Dalton had killed his first man at age 19.

Bob and Lucy Dalton

Deputy Marshal Dalton stated that the killing was in the line of duty.

However, some noted that the dead man had been Dalton’s rival for a woman.

In March 1890, Bob Dalton was charged with bringing forbidden liquor into Indian Territory.

He jumped bail and did not appear for his trial.

In September 1890, Grat was arrested for stealing horses, a capital offense (punishable by death) ; but either the charges were dropped or he was released.

Discredited as lawmen, the Daltons soon formed their first gang.

Their middle brother William M. “Bill” Dalton was already an outlaw, as  he rode with the Wild Bunch.

The gangs were related through the Dalton brother’s mother ,Adeline Younger Dalton, to the Younger brothers, who rode with Jesse James.

 

Outlaws

Bob recruited George “Bitter Creek” Newcomb, Charley Pierce and “Blackfaced” Charlie Bryant to ride with him and his brother Emmett.

Bryant received his nickname because of a gunpowder burn on one cheek.

Grat was visiting his brother Bill in California when the gang was formed, but he joined it later, as did Bill Doolin,

Dick Broadwell, and Bill Power. Their first robbery target was a gambling house in Silver City, New Mexico.

Bill Doolin

On February 6, 1891, after Grat Dalton had joined his brothers in California, a Southern Pacific Railroad passenger train was held up in the town of Alila (Since renamed: Earlimart).

The Daltons were accused of the robbery, based on little evidence.

Grat escaped and Bill was acquitted, but Grat was later arrested, convicted, and given a 20-year prison sentence.

 

According to one account, Grat was handcuffed to one deputy and accompanied by another while being transferred by train.

After the train had gone some distance, one deputy fell asleep and the other was talking to other passengers.

 

Grat’s Shotgun shown in it’s shadowbox and lot 200a, the Sheriff Eugene Kay Handcuff’s used to arrest both Grat and Bill Dalton in 1891

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It was a hot day, and all the windows were open.

Suddenly, Grat jumped up and dived head first out of the train window.

He landed in the San Joaquin River, disappeared under water, and was carried downstream by the current.

The deputies were astounded.

Grat must have taken the key to the handcuffs from the first deputy’s pocket as he slept and timed his escape for when the train would be on a bridge.

If he had landed on the ground, he would likely have been killed.

Grat found his brothers, and they made their way back to Oklahoma Territory.

 

Between May 1891 and July 1892, the Dalton brothers robbed four trains in the Indian Territory. On May 9, 1891, the men held up a Santa Fe train at Wharton (now Perry).

 

They only gained several hundred dollars, but they had worked well as a team.

As they passed Orlando, they stole eight or nine horses.

A posse chased them, but the gang escaped.

Four months later the Dalton gang robbed a train of $10,000 at Lillietta, Indian Territory.

In June 1892, they stopped another Santa Fe train, this time at Red Rock.

“Blackfaced” Charley Bryant and Dick Broadwell held the engineer and fireman in the locomotive.

Bob and Emmett Dalton and Bill Power walked through the passenger cars, robbing the passengers as they went.

Bill Doolin and Grat Dalton took on the express car.

They threw the safe out of the train. They gained little for their efforts—a few hundred dollars and some watches and jewelry from the passengers. The gang scattered after the Red Rock robbery, but soon “Blackfaced” Charley Bryant was captured by Deputy US Marshal Ed Short.

While en route to jail in Wichita, Kansas, Bryant grabbed a gun from a railroad worker assisting Deputy Marshal Short, and in the ensuing gunfight Bryant and Short killed each other.

The gang struck again on July 14, 1892  near the Arkansas border.

Riding eight strong, the Dalton Gang enters Adair, Indian Territory (present-day Oklahoma).

They went to the train station and took what they could find in the express and baggage rooms.

They sat to wait for the next train on a bench on the platform, talking and smoking, with their Winchester rifles across their knees.

They commandeer the train station, preparing to pilfer Katy Train No. 2 (a Missouri, Kansas & Texas passenger train).

When the train glided into the station at 9:42 p.m., the gang boards, capturing members of the train crew without incident and telling them to obey or “have their brains blown out.”

As the crew is marched down to the express car, one of the gang members begins shooting towards the town, evidently trying to discourage  townspeople from getting any ideas about joining the party.

After some resistance, the outlaws break into the express car and force the fireman and the messenger to open the through safe (which contains little loot).

The gang then rifles through the car and loads the collected money into a stolen spring wagon. (Although the exact amount taken is unknown, most historians estimate the take at about $17,000.)

As the robbers load up, Winchester slugs begin whipping very close to the heads of the outlaws.

Eight train guards, including lawmen J.J. Kinney and Capt. J.H. LeFlore, all happened to be at the back of the train when it pulled in.

They fired at the bandits through the windows of the smoking car windows and from behind the train.

The lawmen pour a heavy fire at the crowd around the express car. The robbers use their hostages as shields, while they shoot into the wood building.

Within moments, three of the lawmen inside are hit and knocked out of the fight.

In the gun fight, 200 shots were fired.

The July 21 Indian Chieftain reported the casualties, “A bullet went through the flesh of Mr. Kinney’s shoulder, another struck Johnson’s watch and imbed itself in his arm, while Charley Leflore  had the stock of his gun struck with a shot and the slivers driven into his arm.”

Gang member Charlie Pierce finally shows up with the horses. While one outlaw returns fire at the guards, the others mount up and clatter down the streets of the small town, sending about 20 shots at two men sitting in front of the Skinner Drug Store.

 

Both bystanders are doctors—Dr. W.L. Goff is mortally wounded; Dr. T.S. Youngblood will lose part of his right foot.

(Gang apologists later claim the two men were shot by errant bullets fired by the train guards, yet it is more likely the men were hit by outlaw bullets.)

The gang’s last successful raid is over, but their lawless run is rapidly coming to a violent end.

The robbers fled and disappeared, likely hiding out in one of several caves near Tulsa.

After a flurry of robberies in the Indian Territory (see map, above), Bob Dalton and his gang planned on hitting Red Rock Station.

When the gang got into position at 10:30 p.m. on June 1, Bob didn’t like the look of the darkened smoking car as the train pulled into the small, one-horse station.

Bob sensed that the train carried a car full of loaded Winchesters.

When Glenn Shirley recounted this epiphany in his book, West of Hell’s Fringe, he had Bob tell the gang,

“Look at that smoker.It’s a deadhead, and as dangerous as a rattler.” Bob’s suspicion turned out to be correct. Inside were Wells Fargo detective Fred Dodge and the formidable U.S. Deputy Marshal Heck Thomas, among others.

Letting that train depart, the gang stood by. Soon enough, an unescorted express train arrived, and the gang moved in for the kill. When the gang strong-armed their way into the car, they unfortunately found little money.

The big money had gone through with the first train. The chagrined gang took what was there (less than $3,000) and then mugged a train employee of his gold watch and pocket cash, and, probably just for spite, took the crew’s lunchboxes.

The gang scattered to confuse pursuit but regrouped at one of their favorite caves, supposedly near Tulsa.

There, they discussed raiding the Katy Train at Pryor Creek.

But Bob, who noticed an Indian farmer had spotted them and worried the man would alert the authorities, thought it’d be wise to hit the Katy train at the Adair station instead.

The others agreed.

Although the raid in Adair would end up a success, time was running out for the gang.

 

The Best in the Business

By the time of the train robbery in Adair, the Daltons are already being chased by some of the best lawmen in the business, including Wells Fargo Detective Fred Dodge and Deputy Marshals Heck Thomas and Chris Madsen.

J.J. Kinney, special detective of the railroad, and Capt. J.H. LeFlore, chief of the Cherokee Indian Police, discover the Daltons, by chance, when the gang members board the Adair train.

On July 21, 1892, the  Indian Chieftain report-ed the robbery, stating that once the guards became aware of the robbery, they opened fire at the outlaws through the car windows; the robbers responded in kind.

Heck Thomas

The article also stated, “The railroad and express companies have joined in an offer of $5,000 each ‘for conviction, the aggregate sum not to exceed $40,000.’ Under these terms there will be no pursuit by men of experience in the country. Those who know the Dalton boys, and there can be no doubt but that they were in this hold-up, know they cannot be captured alive.

To kill them does not comply with the terms and will not secure the reward but it will expose whoever does to prosecution in the U.S. Court in Fort Smith.”

And Then There Were Five

With several posses less than 24 hours behind and closing in, Bob Dalton makes a hasty plan and the gang heads north to Coffeyville, Kansas. On this raid, there are only five members—the three Dalton brothers, Bill Power and Dick Broadwell.

Not invited, or perhaps declining, are outlaw stalwarts Bill Doolin, Bitter Creek Newcomb and Charlie Pierce. Some believe Doolin actually does go along but drops out at the last minute because his horse comes up lame or perhaps he has a brief moment of clarity.

Others speculate Bob wants all the glory for the outrageous double heist (besides, the split would be sweeter). In any case, the other members of the so-called Doolin-Dalton Gang do not have long to run.

From their hideout near Tulsa, the Daltons, along with Bill Power and Dick Broadwell, headed for their historic, and disastrous, fate in Coffeyville, Kansas, where they tried to rob two banks.

The Dalton Gang’s Last Raid, 1892

Around 9:30 the morning of October 5, 1892 five members of the Dalton Gang (Grat Dalton, Emmett Dalton, Bob Dalton, Bill Power and Dick Broadwell) rode into the small town of Coffeyville, Kansas.

Their objective was to achieve financial security and make outlaw history by simultaneously robbing two banks

The little town was their former home, and they knew the First National Bank and Congdon National Bank held heavy deposits in the fall after the cattle had been taken to markets.

 

The center of town was built on a triangle formation made of three streets.   It was a small court like place , busy on all days of the week.

The two banks are close together, and the Dalton’s laid plans to rush into to town, divide, plunder both banks and disappear.

This became known and arrangements were made to give them a “warm” reception, for over a week the town triangle was under patrol day and night.

Unbeknownst to the Daltons a US Deputy on their trail had visited a post office in Joplin, while he was there he came across Jack Dodsworth , who displayed much skill as a detective in capturing a gang of mail thieves.

 

It was decided , he would ride six weeks as a spy with the Dalton Gang.

Dodsworth then worked at a post office in Perry, Ok then was transferred to Guthrie, where he became friends with associates of the Dalton Gang.

Under the supervision of US Marshal Nix, the postmaster was apprised of the assignment of Dodsworth which was to stage a hold up of a bank, and then post cards were printed as wanted posters for Dodsworth to gain the goodwill of the Dalton Gang.

Dodsworth was then assimilated into the Dalton Gang as a scout before one of the largest shoot outs of the West in Coffeyville, Kansas.

From the beginning, their audacious plan went astray.

The hitching post at McCoy’s hardware store or at the opera house, where they intended to tie their horses, had been torn down due to road repairs.

Instead, they ride south on Maple and enter a narrow alley where they dismount and tie their horses to a fence.- a fateful decision.

 

To disguise their identity, (Coffeyville was the Dalton’s hometown) two of the Daltons wore false beards and wigs.

Despite this, the gang was recognized as they crossed the town’s wide plaza, split up and entered the two banks.

Suspicious townspeople watched through the banks’ wide front windows as the robbers pulled their guns.

Someone on the street shouted, “The bank is being robbed!” and the citizens quickly armed themselves – taking up firing positions around the banks.

Summoned were George Cubine, a merchant; Charles Brown, a shoemaker; John Cox, express agent; and others who could be conveniently reached.

The Marshall stationed the men around the triangle and hastened his impromptu posse for police duty.

While the Marshall was collecting his force, the bandits, all ignorant of the trap being deliberately made for them, proceeded with their work of robbing the banks.

Grat, 31, is the oldest, but he proves to be a poor leader.

His slow-witted actions in the Condon bank lead to a major debacle

 

Anatomy of a Gun Battle

David Elliott was editor of the local newspaper and published a detailed account soon after the gun battle.

We pick up his story as the desperadoes dismount and head towards their targets:

 

“…After crossing the pavement the men quickened their pace, and the three in the front file went into C.M. Condon & Co.’s bank at the southwest door, while the two in the rear ran directly across the street to the First National Bank and entered the front door of that institution. The gentleman [the observer] was almost transfixed with horror.

He had an uninterrupted view of the inside of Condon and Co.’s bank, and the first thing that greeted his vision was a Winchester in the hands of one of the men, pointed towards the cashier’s counter in the bank.

 

He quickly recovered his lost wits, and realizing the truth of the situation, he called out to the men in the store that ‘The bank is being robbed!’ Persons at different points on the Plaza heard the cry and it was taken up and quickly passed around the square.

At the same time several gentlemen saw the two men enter the First National Bank, suspecting their motive, followed close at their heels and witnessed them ‘holding up’ the men in this institution.

They gave the alarm on the east side of the Plaza. A ‘call to arms’ came simultaneously with the alarm and in less time than it takes to relate the fact a dozen men with Winchesters and revolvers in their hands were ready to resist the escape of the unwelcome visitors.”

As the townspeople arm themselves, the desperados enter the two banks – Bill Powers, Dick Broadwell and Grat Dalton the C.M. Condon bank, Bob and Emmett Dalton the First National. Inside the Condon Bank, three employees are forced at gunpoint to fill a sack with money.

One brave teller declares to the robbers that the vault has a time lock and can’t be opened for another 10 minutes (this was untrue.)

The robbers decide to wait, however their plan is interrupted as the townspeople open fire:

Evidently recognizing that the fight was on, Grat Dalton asked whether there was a back door through which they could get to the street. He was told that there was none.”…Just at this critical juncture the citizens opened fire from the outside [of the Condon Bank] and the shots from their Winchesters and shot-guns pierced the plate-glass windows and rattled around the bank.

Bill Powers and Dick Broadwell replied from the inside, and each fired from four to six shots at citizens on the outside. The battle then began in earnest.

He then ordered Mr. Ball and Mr. Carpenter [two bank employees] to carry the sack of money to the front door.

Reaching the hall on the outside of the counter, the firing of the citizens through the windows became so terrific and the bullets whistled so close around their heads that the robbers and both bankers retreated to the back room again.

Just then one at the southwest door was heard to exclaim: ‘ I am shot; I can’t use my arm; it is no use, I can’t shoot any more.’ “

Meanwhile, inside the First National Bank

Safe that was in the vault of the First National Bank and contained  the banks currency and gold reserves

A similar scene played out at the First National where Bob and Emmett Dalton forced the bank’s employees to fill their sack with money. Using the employees as shields, the robbers attempted to escape the bank, only to be driven back inside by heavy gunfire:

“…He [Bob Dalton] then ordered the three bankers to walk out from behind the counter in front of him, and they put the whole party out at the front door. Before they reached the door, Emmett called to Bob to ‘Look out there at the left.’

Just as the bankers and their customers had reached the pavement, and as Bob and Emmett appeared at the door, two shots were fired at them from the doorway of the drug store… Neither one of them was hit.

They were driven back into the bank… Bob stepped to the door a second time, and raising his Winchester to his shoulder, took deliberate aim and fired in a southerly direction.

Emmett held his Winchester under his arm while he tied a string around the mouth of the sack containing the money. They then ordered the young men to open the back door and let them out.

Mr. Shepard complied and went with them to the rear of the building, when they passed out into the alley. It was then that the bloody work of the dread desperadoes began.”

Alley of Death

Many of the townspeople gathered in Isham’s Hardware Store near the banks. Not only did the unarmed citizens get rifles, shotguns, and ammunition, but the store also provided an excellent view of the two banks and the alley where the gang had tied their horses:

 

“…The moment that Grat Dalton and his companions, Dick Broadwell and Bill Power, left the bank [the C.M. Condon Bank] that they had just looted, they came under the guns of the men in Isham’s store.

Grat, Dalton, and Bill Powers each received mortal wounds before they had retreated twenty steps.

The dust was seen to fly from their clothes, and Powers in his desperation attempted to take refuge in the rear doorway of an adjoining store, but the door was locked and no one answered his request to be let in.

He kept his feet and clung to his Winchester until he reached his horse, when another ball struck him in the back and he fell dead at the feet of the animal that had carried him on his errand of robbery.

Back of Isham’s Hardware

Grat Dalton, getting under cover of the oil tank, managed to reach the side of a barn that stands on the south side of the alley… [At this point, Marshal Connelly ran across a vacant lot into “Death Alley” from the south to the spot where the bandits had tied their horses.] The marshal sprang into the alley with his face towards the point where the horses were hitched.

This movement brought him with his back to the murderous Dalton, who was seen to raise his Winchester to his side and without taking aim fire a shot into the back of the brave officer. Marshal Connelly fell forward on his face within twenty feet of where his murderer stood.

Dick Broadwell in the meantime had reached cover in the Long-Bell Lumber Company’s yards, where he laid down for a few moments. He was wounded in the back. A lull occurred in the firing after Grat Dalton and Bill Power had fallen.

Broadwell took advantage of this and crawled out of his hiding-place and mounted his horse and rode away.

A ball from Kloehr’s [John Kloehr, a townsman] rifle and a load of shot from a gun in the hands of Carey Seaman overtook him before he had ridden twenty feet.

Bleeding and dying he clung to his horse and passed out of the city… His dead body was subsequently found alongside of the road a half-mile west of the city.

[As Marshal Connelly fell, Bob and Emmett Dalton – successfully escaping the First National Bank – ran down a side alley and into ‘Death Alley’ from the north.]

When the two Daltons reached the junction of the alleys they discovered F.D. Benson in the act of climbing through a rear window with a gun in his hand.

 

Divining his object, Bob fired at him point blank at a distance of not over thirty feet.

The shot missed Mr. Benson, but struck a window and demolished the glass.

Bob then stepped into the alley and glanced up towards the tops of the buildings as if he suspected that the shots that were being fired at the time were coming from that direction. As he did so, the men at Isham’s took deliberate aim at him from their position in the store and fired.

The notorious leader of the Dalton gang evidently received a severe if not fatal wound at this moment.

He staggered across the alley and sat down on a pile of dressed curbstones near the city jail. True to his desperate nature he kept his rifle in action and fired several shots from where he was seated.

His aim was unsteady and the bullets went wild… He arose to his feet and sought refuge alongside of an old barn west of the city jail, and leaning against the southwest corner, brought his rifle into action again and fired two shots in the direction of his pursuers.

A ball from Mr. Kloehr’s rifle struck the bandit full in the breast and he fell upon his back among the stones that covered the ground where he was standing.

After shooting Marshal Connelly, Grat Dalton made another attempt to reach his horse. He passed by his fallen victim and had advanced probably twenty feet from where he was standing when he fired the fatal shot. Turning his face to his pursuers, he again 

Emmett Dalton had managed to escape unhurt up to this time. He kept under shelter after he reached the alley until he attempted to mount his horse.attempted to use his Winchester. John Kloehr’s rifle spoke in unmistakable tones another time, and the oldest member of the band dropped with a bullet in his throat and a broken neck.

A half-dozen rifles sent their contents in the direction of his person as he undertook to get into the saddle… Emmett succeeded in getting into the saddle, but not until he had received a shot through the right arm and one through the left hip and groin.

During all this time he had clung to the sack containing the money they had taken from the First National Bank.

Instead of riding off, as he might have done, Emmett boldly rode back to where Bob Dalton was lying, and reaching down his hand, attempted to lift his dying brother on the horse with him. ‘Its no use,’ faintly whispered the fallen bandit, and just then Carey Seamen fired the contents of both barrels of his shot-gun into Emmett’s back.

He dropped from his horse, carrying the sack containing over twenty thousand dollars with him, and both fell near the feet of Bob, who expired a moment thereafter.”

After the battle – Bill Power, Bob Dalton, Grat Dalton and Dick Broadwell

Emmet Dalton survived despite receiving 23 gunshot wounds.

After serving 14 years in prison for the crime, Dalton capitalized on his notoriety to author books and become an actor in Hollywood. He died in 1937 at the age of 66.