Dalton Gang

Beginnings

James Lewis Dalton from Jackson County, Missouri, and Kentucky was the father of all four boys. He was a saloon keeper in Kansas City, Missouri, when he married Adeline Lee Younger. Through her half-brother, Adeline was an aunt of Cole and Jim Younger, of the James–Younger Gang. The Daltons may have been inspired by their famous cousins' exploits— the Youngers were much older and imprisoned at the time of the Dalton Gang's activities.

The Dalton children were:

Charles Benjamin "Ben" Dalton (1852–1936)

Henry Coleman "Cole" Dalton (1853–1920)

Littleton "Lit" Lee Dalton (1857–1942)

Franklin "Frank" Dalton (1859–1887)

Gratton Hanley "Grat" Dalton (1861–1892)

William Marion "Bill" Dalton (1863–1894)

Eva May Dalton (1867–1939)

Robert Rennick "Bob" Dalton (1869–1892)

Emmett Dalton (1871–1937)

Leona Randolph Dalton (1875–1964)

Nancy May Dalton (1876–1901)

Simon Noel "Si" Dalton (1878–1928)

The brothers who were members of the Dalton Gang were Bob, Grat, Emmett, and Bill.

Lawmen

On November 27, 1887, Frank Dalton and another deputy marshal, Jim Cole, went across the river from Fort Smith to arrest three whiskey bootleggers. As they approached the camp the bootleggers began to fire on them. Frank shot and killed two, but his gun jammed and he was killed by the remaining bootlegger. His deputy abandoned him after being wounded. Frank is buried in Coffeyville, Kansas.

After Frank's death, Grat moved back from California and took over his brother's job as deputy marshal at Fort Smith. He also brought Bob along as a posse member. In August 1888, the two formed a posse to arrest a man named Charley Montgomery. Montgomery was alleged to be posing as a deputy marshal. Bob discovered his location in Timber Hills while Grat was away searching in Coffeyville and went ahead to lead the posse in making the arrest himself before Montgomery could escape the territory. The stakeout ended in Montgomery’s death.

In January 1889, Grat and Bob both became deputies first under Marshal Jones and later under Marshal R.L. Walker in Wichita. Looking to earn more money, Bob also became part of the Osage Nation police force in addition to his job as a deputy. Unlike the marshals office, the Osage Police paid a monthly salary. Bob also hired Emmett under him to guard prisoners.

Outlaws

Alila Robbery

On the night of February 6, 1891, two masked men carrying 44-calibre revolvers held up a Southern Pacific Railroad passenger train near the town of Alila (present day Earlimart, California). The outlaws had worn masks during the Alila robbery, concealing their identities. Some years later, Lit Dalton asserted that Bob and Emmett had told him many times that they had robbed the train.

Bob and Emmett were hiding out in a ranch barn a mile west of Malaga, and after arriving the brothers talked until morning. Lit noticed that Grat's horse was indeed limp and agreed to help Grat sell it. Since the horse was lame, they could only get $60 for it and Grat was unable to find another horse afterwards. Grat shipped his saddle and riding rig to Delano and took the train to Traver where he met Bob and Emmett. They played poker all night in Traver and then traveled to Tulare to do the same. They had been following the Southern Pacific pay car as it made its way down the valley from Oakland to Bakersfield to pay railroad employees. This train was always accompanied by a crowd of gamblers and prostitutes, and Grat and Bob had "followed the pay car" together several times before.

Pursuit across the Southwest

In the two weeks following the robbery, Bob and Emmett hid out in the mountains near Bill's ranch. Bill left his brothers supplies and food and obtained horses to evade pursuit.

Despite these efforts, Bill was arrested in Paso Robles by Sheriff Kay and taken to Visalia. After a hearing, Bill was held for trial for the Alila robbery, but he secured bondsmen and was released.

Sheriff Kay decided to pursue Bob and Emmett with his deputy, Jim Ford.

Kay tracked the Daltons to their mother's home, and kept watch of the house for a few days before being forced to return to Kingfisher because of bad weather. When he returned the next day to watch the house, he discovered that Bob and Emmett had escaped. Kay talked to their mother for several hours and she even invited him in for breakfast. She denied any wrongdoing by her sons, stating that they were in fact lawmen, and told Kay they had gone to Guthrie if he wanted to talk with them.

Kay and Ford traveled the fifty miles to Guthrie, but soon came into problems when dealing with different tribal jurisdictions. At Guthrie, Kay and Ford noticed that there had been some sort of celebration the night before as they were greeted by three white men hanging from a large tree at the entrance to town and noticed the streets were lined with several groups of black men playing Craps on the sidewalks. Kay found out that, before they had arrived, Bob and Emmett had got into a fight at one of the saloons there and badly beat up two cowboys before leaving for Topeka.

Sheriff Kay was forced to give up the chase in order to return to California for Grat's trial. The Daltons had plenty of friends in the area willing to hide them and easily lost Kay once they were in familiar territory. After they realized they were no longer being pursued, Bob and Emmett began to form what would be known as the Dalton Gang.

Grat's trial

For the four months that Bob and Emmett spent trying to lose Sheriff Kay in the desert, Grat sat in the Tulare County jail in Visalia awaiting his trial. After securing bondsmen, Bill immediately went to Merced and hired John W. Beckenridge, the best attorney in the San Joaquin Valley, to defend Grat. What Bill did not know is that Beckenridge was also a consulting attorney for the Southern Pacific railroad. To help pay him the two thousand dollars he asked for, Bill sold almost all of his horses and mules. Their mother also came to California from Kingfisher to pay Beckenridge after she mortgaged her home and borrowed money from neighbors. She then traveled to Visalia with her two daughters, as well as her sons Ben, Cole, Lit and Bill, for Grat's trial.

Grat's trial did not start until that June and it lasted three weeks. Though much of the evidence showed that Grat was in Fresno the night of the Alila robbery, including the testimony of several witnesses, the influence of the powerful Southern Pacific Railroad caused him to receive an unfair trial. Beckenridge showed up to the trial late and drunk, and neither the defense, nor the prosecution mentioned that the fireman had been accidentally killed by the expressman. This was unknown to Grat, since the Dalton brothers had all assumed that Emmett had killed the fireman. Almost all of Beckenridge's witnesses were bar keepers, gamblers, saloon hangers-on, or pimps. Sheriff Kay even pointed out during the trial that Beckenridge had overlooked Grat's rights. Southern Pacific detective Will Smith visited Grat's cell almost every day during the trial trying to get a confession out of him and Grat began to despise Smith.

Kay knew that, besides Beckenridge's sabotage of the case, Grat would probably be found innocent and their case against Bob and Emmett would fall through.

Towards the end of the trial, Sheriff Kay, Detective Smith, and District Attorney Power talked to Grat while taking him back to his cell from the court room when Beckenridge was not present. Kay told Grat that he knew neither Bob or Emmett killed the fireman. He offered to admit this in court if Grat and Bill told the true story of the robbery. Detective Smith decided to chime in, but Grat said he would not say a word while Smith was present. Smith was told to leave and both Bill and Grat agreed to tell their story, but only if they showed that there was no first degree murder in the robbery. The Daltons told their stories, but neither Kay or Beckenridge ever cleared up the murder point and ruined Grat's case.

Ceres robbery

Grat was taken back to jail to await his sentence. While in jail, a train robbery occurred near Ceres, on September 3, 1891, but was unsuccessful with no money being taken. The only evidence found at the robbery was a coat made from a tailor from Visalia. Kay suspected that this was probably the work of some suspects he had from Visalia, but the railroad detectives demanded the arrest of the remaining Dalton brothers. Kay telegraphed his deputy George Witty and told him to check on Bill Dalton and to immediately notify him when he was found. Kay checked on his Visalia suspects, who at the time were running a livery stable in Modesto, and was convinced they were not involved with the Ceres robbery. He then went to Fresno to check on Lit and Cole Dalton, and was convinced of the same.

When Kay returned to Visalia, he immediately went with detective Smith to the tailor of the coat found at the Ceres robbery. The tailor remembered the coat, but he could not remember who had bought it, only that some girl had picked it up once it was clean. After Kay finished talking to the cleaner, Deputy George Witty reported to him that telegrams from the coast said Bill was not in Paso Robles or Estrella. Neither was he in Merced or Livingston. Witty did have a clue from another deputy that two strange men had been seen hanging around after dark on the open plain near Traver and at the abandoned Overland Stage station at Cross Creek. Kay suspected that Bob and Emmett might be back in California to free Grat from jail, and took Deputy Witty with him to the Cross Creek station in his buggy.

Late in the afternoon, Kay and Witty were about four hundred yards from the station when they saw two men crouching as they crossed the road from the old stage barn to the station. Kay's buggy was directly facing the setting sun, so they could not tell who the men were. The road curved behind some willow trees, and Kay told Witty to drive past the house, passing close to the door, and then to drive back. With his revolver in hand, Kay dropped to the ground as they passed the door and slowly entered the station. Maggie Rucker, the woman who once ran the Cross Creek Overland station, was sitting with another girl alone in the front room, silently making dresses. Kay asked Rucker if there was anyone else around and she replied that there was not. Right as she said this, Kay heard someone rush across the floor of an adjoining room and through the crack in the door he could see a man taking position at the window.

Kay moved quietly across the floor and pushed the door a little farther open with his revolver. Standing with his back towards him was Bill Dalton, watching the horses and buggy Kay had just left, while nervously working the lever of his winchester. Kay nudged the door open with his elbow, aimed his revolver at Bill and said, "Bill! Hello!". Bill, thrown off his guard, quickly turned around and mimicked the greeting, "Kay! Hello!". He then threw the butt of his winchester to the ground and the two nervously laughed at each other. Kay had Bill put his rifle down, backed him into the front room, and checked him for any other weapons. When they came back into the front room both Maggie Rucker and the girl remained quiet as they both expected Kay to have been killed.

Formation of the gang

Bob and Emmett, meanwhile, had been busy in Oklahoma forming their gang. After their unsuccessful career in California, they decided they could do much better in their home country, and unlike their first attempts, they began carefully planning their robberies. As a former lawman, Bob knew the difficulty officers had enforcing laws in Indian and Oklahoma Territories. While the Indian Nations had their own tribal law enforcement, these agencies had no jurisdiction over non-Indians. The newly formed Oklahoma Territory had organized their own sheriff and city police departments, but there was so far very little cooperation between them. The only agency with jurisdiction over the whole territory was the U.S. Marshals Service, but it was quickly becoming fragmented due to power struggles between newly formed district courts and jealousy between marshals over their different jurisdictions. There was also little incentive among Deputy Marshals to search for potentially dangerous outlaws, their only pay being for fees and a set amount for each criminal they arrested. Unless there was a high enough reward being offered, they would instead choose to focus their attention on petty criminals.

With Bob as the leader, the boys recruited mostly men who had grown up with them in Oklahoma. First recruited were George "Bitter Creek" Newcomb and "Blackfaced" Charlie Bryant, who had received his nickname because of a gunpowder burn on one cheek. Even though Sheriff Kay had given up his pursuit of the boys, they still had a $3000 bounty on their heads posted by Wells Fargo and the Southern Pacific Railroad, encouraging lawmen in the area to pick up where Kay had left off. Leading the pursuit was Bob's old friend, Deputy Marshal Heck Thomas, whose renowned skills as a deputy kept the gang constantly on the move and in hiding. Angered by the charges against Grat and Bill which he knew to be false, Bob decided that the best way to help his brothers would be to acquire enough money to pay for their bail and defense. This resulted in the first robbery at Whorton, May 1891, where the gang stole $1200.

Joining afterwards were Bill Doolin, Dick Broadwell, Bill Powers, and Charley Pierce. The gang was also assisted by Bob's lover Eugenia Moore, known by her aliases "Tom King" and "Miss Mundays", who acted as their informant, but was also a notorious horse thief and outlaw.

When not preying on the railroads, the gang spent their time digging out large rooms into the steep hills in the cedar brakes on the Northern Canadian River. This was on the property of a man named Jim Riley, about eight miles from the present-day town of Taloga, Oklahoma. The deep canyons of the area, covered with dwarf cedar and blackjack oaks, made it an ideal hiding place. Riley would feed the outlaws, and would do the same for any passing officers, but he would never reveal each other's whereabouts to either parties.

Grat's escape

On September 21, Grat Dalton was brought into court to face sentencing, but this was instead postponed to October 6. This was a date that Grat had no intention on making. Rumors had circulated for months that Bob had planned to come and liberate Grat, so two of sheriff Kay's deputies, Jim Wagy and Bob Hockett, had been hired by Wells Fargo to guard Grat's cell until he was sentenced and sent to San Quentin. This was in addition to the jailer, J.M. Williams. One night, Jim Wagy heard a noise in the basement and upon investigation discovered that someone had tried to break the lock to the grated window. He decided to watch the outside of the place at night to see if he could catch in the act whoever was trying to open the grating. Wagy hid all night in a yard across the street but saw nothing. Instead he caught a cold from sitting in the fog all night. The next morning, Grat called Wagy over to his cell and asked him where he got such a cold. Wagy told him that he must've slept in a draft, to which Grat replied, "Yes, it must have been pretty cold in the yard over there last night." Grat could not see the yard Wagy had laid in from his cell and the deputy had not told anyone what he had done that night. Expecting there to be an escape, and because none of the other deputies would listen to him, Wagy decided to quit.

On the night of September 27, Grat and two cellmates, Arvil Beck and W.B. Smith, escaped from the Tulare County jail in Visalia while Sheriff Kay was in San Francisco. At first, it looked to Kay as if it had been an inside job as it was obvious Grat had simply unlocked the cell door with a key and broke through the basement window to get out. They did however find pieces of a file and a hack saw blade in the prisoner's toilet. Bill had been in a separate cell from Grat, located upstairs. When approached by Kay, Bill told him, "The boys were there when I went to sleep, and when I awakened they had unlocked and gone. Why in the world do you suppose they went away and left me behind?"

Jim Wagy also showed up after the break out to overlook the scene. By that time, Bill had been moved downstairs into what was Grat's cell. When Jim approached Bill said, "Jim, the birds have flown." When they entered the cell, Bill took out his guitar, sat on a soap box, leaned against the bars of the corridor and began to play a popular song he put his own words to and titled, "You'll Never Miss My Brother Till He's Gone". While Bill was playing his guitar, Wagy noticed that he was trying to cover up where the break had been made. One of the bars had been cut out and replaced with a broom handle blackened by soot. Wagy said, "Here is your hole", and kicked the broom handle onto the floor. Bill immediately threw his guitar on the bed and exclaimed, "Now what in the world do you know about that? How did they ever cut that bar out without my knowing it?"

Oklahoma

Grat returned to Oklahoma in the spring of 1892 and shortly afterward joined his brothers gang. Some time later, the three dissatisfied members also returned and new plans began to form. Bill had returned to Oklahoma several months earlier, living at his mother's house near Kingsfisher. After being found innocent by a Visalia jury, Bill was acquitted and released on October 15. He then sold the lease to his ranch in San Luis Obispo County, moved his family to his wife's parents in Livingston, California, and left for Kingfisher. Though he did not participate in any of the hold-ups with his brothers, he acted as their spy and advisor.

On June 1, 1892, the gang robbed the Santa Fe train at a small station called Red Rock at 10pm. Here, the Santa Fe had found out about the Daltons' plans and attempted to set up a trap for the gang, filling the train with heavily armed officers. They made the mistake of leaving the train dark, though, which made Bob suspicious, and the gang allowed the train to go by. They then robbed the next train a few minutes later, securing about $50,000. The $50,000, however, came out to only $1800 after drafts and securities had been thrown out. After splitting the money among themselves, the gang soon realized they needed to rob another train.

The night before the robbery at Red Rock, Judge Burford, US District Attorney for Oklahoma Horace Speed, and deputy marshal George Yoes (son of Marshal Jacob Yoes, the Daltons former employer at Fort Smith) were sitting in a hotel lobby in Kingfisher, where they were talking about the cases that would be in court the next day. Bill Dalton came into the hotel lobby and began to speak to deputy Yoes in a loud voice, so everyone around them could hear. At 10pm he looked at his watch and announced to Yoes aloud that it was his bedtime, but that he would be back to have breakfast with him in the morning. After he left, the judge asked Yoes who the man was, as he seemed educated and well-informed. Yoes told the judge that he was Bill Dalton, the brother of the notorious train robbers, and the judge asked him to introduce them when he came to breakfast. Bill arrived for breakfast like he said, and the four of them took the same table. At about 8am, a telegraph messenger came into the room and handed the deputy marshal a telegram, reporting the robbery at Red Rock by the Daltons at 10pm the previous night. The deputy handed the message to Judge Burford, who read it aloud to the audience. As soon as the judge had finished, Bill announced, "Well, I can prove that I was not there, and not by accident either."

The next robbery was on July 14, at Adair, Oklahoma, near the Arkansas border. At the station, the gang 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. When the train came in at 9:45 pm, they backed a wagon up to the express car and unloaded all the contents. The eight armed guards on the train all happened to be at the back of the train when it pulled in. They fired at the bandits through the car windows and from behind the train. In the gunfight, 200 shots were fired. None of the Dalton gang was hit. Doctors W. L. Goff and Youngblood were sitting on the porch of the drug store near the depot. Both men were hit several times by stray shots; Dr Goff was fatally wounded. Also wounded were captains Kinney and LaFlore, but they recovered. The gang secured about $18,000. They were also accused of robbing a bank in El Reno, Oklahoma, on July 28, but this was based on little evidence, as no one identified any members of the gang.

Coffeyville bank robbery

Bob Dalton had ambitions. He would, he claimed, "beat anything Jesse James ever did—rob two banks at once, in broad daylight." On October 5, 1892, the Dalton gang attempted this feat when they set out to rob the C.M. Condon & Company's Bank and the First National Bank on opposite sides of the street in Coffeyville, Kansas. Bob had planned the entire robbery. Emmett, however, was against the idea. He had gone to school at Robbins Corners near Coffeyville, and knew several hundred people in town. He was afraid some of his friends would be hurt, but Bob assured him there would not be any shooting, and that it would all be over before anyone knew what happened. The plan was that Bob and Emmett were to rob the First National Bank while Grat, Broadwell, and Powers robbed the Condon Bank across the street. Emmett thought Grat would mess things up if he went alone with Powers and Broadwell, and thought they should trade places. This led to a heavy argument between Bob and Emmett and created bitterness between them on the way to the robbery.

Bob had planned for the gang to tie their horses to a post behind the Condon Bank, where it was protected from the center of town by brick walls. They had not been to the town for several years, though, and the hitching post had since been removed during street work. Bob would not allow Emmett to check out the town beforehand in fear that he would be recognized, so this was not factored into their plan. When they arrived, Bob had to think quickly, and decided instead to tie their horses in an alley across from the bank to the west, near the city jail, which offered them little protection. This is now known as Death Alley.

On the morning of October 5, the gang emerged from the alley onto the plaza of Coffeyville. A storekeeper who was sweeping the sidewalk a few feet away noticed Bob, Emmett, and even Grat, who was wearing a fake mustache, and ran inside his store. In close order, the five crossed Walnut Street from the alley to the Condon Bank, holding Winchester rifles close along their legs. Grat, Broadwell, and Powers entered the Condon Bank and Emmett and Bob hurried across Union Street to the First National Bank. Street work was being done at the time, and one of the workers noticed the men dog-trotting across the alley with rifles, and began to yell, "The Daltons are robbing the bank!" Very soon, half the businessmen around the plaza knew what was going on, and the message quickly passed throughout the town.

Grat entered the Condon Bank and pointed his Winchester at the cashier, ordering his hands up, while Powers and Broadwell took positions at the door. Grat went to the back office and ordered the manager into the front, he then handed the cashier a sack bag and ordered him to fill it with cash from the money drawer. Then, noticing the vault door was open, Grat ordered both of them into the vault, where the safe with the gold was. When told to open the safe, the manager lied, telling Grat it was a time lock and that it would not open for another 10 minutes. Grat believed him and decided he would wait until it opened. He then ordered the bags of silver on the vault floor into his bag, containing $1000 and weighing about 200 lb.

Afterward

For a time, Bill Doolin and his partners operated under outlaw Henry Starr (Cherokee), hiding out about 75 miles northeast of Kingfisher, from where they made several raids. Doolin, Newcomb, and Pierce visited the Daltons' mother in Kingfisher to console her after her sons' deaths. Brothers Lit and Bill Dalton were also visiting their mother, and Doolin proposed that they join his group to avenge their brothers. Bill Dalton agreed to join them and soon took part in several robberies, but Lit refused in disgust. Henry Starr was arrested in 1893 and held for trial at Fort Smith.

As Doolin and Dalton were accepted as leaders of the gang, it became known as the Doolin-Dalton Gang, and also as the Wild Bunch. Dalton took part in several robberies with the Wild Bunch, including a gun battle on September 1, 1893, at Ingalls, Oklahoma Territory, where three deputy U. S. marshals were killed. Eventually, Bill Dalton left Doolin to form his own Dalton Gang. On May 23, 1894, Dalton and his new gang robbed the First National Bank at Longview, Texas. During the robbery, one member of the gang and four citizens were killed in a shootout. This was the gang's only job. After the gang separated with their share of the loot, Bill hid out with his family in a cabin near Elk, Indian Territory. A posse assembled by U.S. Marshal S.T. Lindsey in Ardmore, Oklahoma, tracked him to the cabin and surrounded it on June 8, 1894. Bill escaped through a window at the back of the house, but as he ran through a patch of corn he was shot and killed by the deputy marshals.

Lit, the last surviving Dalton brother, responded to a book written by his brother Emmett after the latter's death. Lit said that Emmett's book, When the Daltons Rode (1931), was largely fabrication. Emmett had denied accompanying Bob to California. On his death bed, Emmett told Frank Forrest Latta that he had robbed a train in California, and had used the alias William McElhanie. He asked Latta not to publish the information until after his death.

In her unpublished novella, Grat Dalton's Ride, Eva Evans, the daughter of the famous California outlaw Chris Evans, tells the story of Grat Dalton's escape from California after the Alila robbery. In it she implied that her father was the one who helped Grat Dalton escape from the Visalia Jail, lending credibility to an earlier claim made by Sheriff Gene Kay of this being true. Most of Sheriff Kay's information on Chris Evans came from his deputy Perry Byrd, who also happened to be Evans' brother-in-law, but Kay had other supporting information as well.

In popular culture

A largely fictional film version of the Daltons' lives was adapted from Emmett's 1931 book, When the Daltons Rode. Released in 1940, it starred Randolph Scott, Broderick Crawford, and Brian Donlevy.

The Daltons were featured in Randolph Scott's Western, Badman's Territory (1946).

The Daltons were also featured in yet another Randolph Scott Western, Return of the Bad Men (1948), loosely based on Doolin's leadership of an outlaw gang in Oklahoma Territory, combining the remnants of the original Dalton gang with new members to become the Wild Bunch.

Randolph Scott himself plays Bill Doolin in the film The Doolins of Oklahoma (1949), in which he is depicted as a reluctant outlaw forced into a leadership role by circumstances after the Coffeyville raid.

The motion picture The Cimarron Kid (1952), about the Dalton Gang, starred Audie Murphy as Bill Doolin.

"The Dalton Gang" is a half-hour, 1954 episode of the American TV series Stories of the Century with Myron Healey as Bob Dalton, Fess Parker as Grat, Robert Bray as Emmett, and John Mooney as Bill Dalton.

The 1954 Franco-Belgian comic book Hors-la-loi, part of the Lucky Luke series, embroiders the Coffeyville events, with the gang made up only of Dalton brothers, all four of whom are killed in the end. Morris's comical depiction of the outlaws — as mustachioed and identically dressed quadruplets differing only in their height — having proved popular, a second fictional gang of Dalton brothers physically indistinguishable from the originals and presented as their (bungling) cousins became recurring villains in the Lucky Luke series, later written by René Goscinny. These were also depicted in several films including La Ballade des Dalton (animated feature, 1978), Lucky Luke (1991) and Les Dalton (2004).

The Dalton Girls (1957) is a fictional Western B-film in which Dalton sisters continue in the ways of their brothers.