Altogether, Lewis Dalton from Jackson County, Missouri, had eight sons.  Lewis was a saloon keeper in Kansas City when he married Adeline Younger, an aunt of Cole and Jim Younger.  Lewis and Adeline named their sons Charles Benjamin (1853-1936), Henry Coleman (1853-1920), Littleton Lee (1857-1942), Franklin (1859-87), Gratton Hanley (1861-92), William Marion (1863-94), Robert Rennick (1869-92), Emmet (1871-1937), and Simon Noel (1878-1928).  One of these boys, Frank, would become a respected lawman; four would earn their reputations as dangerous outlaws: Bob, Emmett, Grat, and Bill.

This is their story.

Deputy US Marshal Frank Dalton

Frank Dalton was appointed a Deputy United States Marshal under Judge Isaac Parker at Fort Smith, Arkansas for the jurisdiction of the Oklahoma Territory.  By every account, Frank was the family’s success story.

Most of the present-day Oklahoma was set aside by the Federal government as Indian territory before the American Civil War.  It was opened for general settlement in 1890, initially populated by farmers and ranchers.   Oklahoma was often called the twin territories because a portion of the territory had been set aside for American Indian (Amerind) reservations —another for white settlement.  Its vast unpopulated northwestern section became a refuge for outlaws.  As Judge Parker had legal jurisdiction over the Oklahoma Territory, his deputies frequently combed Oklahoma for murderers, rustlers, and thieves.  When apprehended, deputies would transport them back to Fort Smith to answer for their crimes.

As one of Parker’s deputies, Frank Dalton was involved in a number of high-risk encounters with outlaws; that was his job.  He served as a deputy for over three years.  On 27 November 1887, he and deputy J. R. Cole were seeking members of the Smith-Dixon gang.  Smith-Dixon cohorts were horse thieves and whiskey peddlers operating within the Indian Territory.  Its members included Dave Smith, a former member of the Belle Starr gang, his brother-in-law Leander (Lee) Dixon, and William (Billy) Towerly.

Dalton and Cole tracked them to a wood camp in the Arkansas River bottoms near present-day Sequoyah County.  At the camp was Dixon’s wife.  Approaching the camp, the deputies announced their presence, adding they were only after Smith and that the others should not interfere.  Smith immediately fired off a shot, hitting Dalton in the chest and he fell to the ground.  Cole returned fire, killing Dave Smith.  At that moment, Lee Dixon and Billy Towerly began firing at Cole, who wounded, took cover behind a tree.  Towerly then ran toward Dalton, who was still conscious and pointed his gun in Dalton’s face.  Dalton said, “Don’t shoot.  I’m already dying.”  Towerly then shot Dalton in the face and once again in the head for good measure.

From his position behind the tree, Cole continued firing.  Dixon’s wife was killed, Dixon was wounded, and Towerly fled the camp.  Cole gathered his horse and returned to Fort Smith, where he reported what happened.  The US Marshal sent a posse to retrieve the bodies of Smith, Dalton, and Mrs. Dixon.  Lee Dixon’s wound was near his left collar bone.  He was taken to the Fort Smith hospital but later died of his wounds.

Towerly was now a man wanted for the murder of a deputy US marshal; the reward was $1,000.  In early December, deputies Bill Moody and Ed Stokely caught up with Towerly near Atoka, Oklahoma, his parent’s home.  The deputies approached the home and demanded that Towerly surrender.  Billy opted for curtain number two, which was to draw down on two deputy marshals.  As Billy went for his gun, the two deputies drew their weapons and fired.  Towerly was hit in the leg and shoulder.

Stokely approached the wounded man to disarm him but Towerly was still interested in the least happy outcome.  Switching his revolver to his other hand, Towerly shot Stokely in the chest, killing him.  Moody fired again and killed Towerly.

Frank Dalton was laid to rest at Coffeyville, Kansas —the town where two of his brothers were later killed during an attempted bank robbery.

California Congressman William M. Dalton

Bill Dalton seemed initially destined to follow Frank’s example.  For a time, he served in the California legislature, but it may have occurred to him that if he was going to be a crook, he may as well get top dollar for it.  In 1890, Bill and his brothers robbed a train just outside of Los Angeles.  No one ever suggested that Bill Dalton (or any of his brothers, for that matter) were particularly good at crookery, and nowhere was this better demonstrated of this than by the fact that Bill and Grat were soon captured after their train robbery.  Both men escaped capture.  After Bill learned that Bob and Grat had been killed in Coffeyville in 1892 and that Emmett had been wounded and captured, Bill headed for the Oklahoma Territory. This is where he met Bill Doolin.  They soon formed their own gang, which had several monikers: they were the Doolin-Dalton Gang, the Oklahombres, and the “Wild Bunch.”

Some academics claim that Dalton was obsessed with becoming more famous than his brothers, and that he and Doolin went to great efforts to see that happen. For three years they committed a series of bank robberies, stagecoach holdups, and train robberies.  They pulled these jobs at several locations: Oklahoma, Texas, Arkansas, and Kansas.   Deputy US marshals under Evett Dumas (“E. D.”) Nix tracked them to Ingalls, Oklahoma.  The supervisory officer was Deputy US Marshal John Hixon.  Hixon’s posse first engaged “Bitter Creek” Newcomb, which led to a shootout that left Newcomb badly wounded.  A large number of outlaws then opened fire from inside a saloon, and the deputies returned fire, killing one horse and forcing the outlaws to flee to a nearby stable.  While the outlaws were making their way out of the saloon, its owner engaged the marshals from the doorway of his saloon, and he was soon wounded and placed under arrest[1].

From a good position, “Arkansas Tom” Jones opened fire on the marshals with a rifle and was able to push them back to find cover.  While this was going on, the outlaws prepared to make their escape on horseback.  It was in this engagement that Deputy Marshal Tom Hueston was mortally wounded[2].  Two innocent bystanders were hit in the exchange; one killed, one wounded.  Bill Doolin shot and killed Deputy Marshal Richard Speed.  Deputy Lafayette Shadley fired at Dalton, hitting his horse in the leg, which toppled Dalton from his horse.  Dalton returned fire, mortally wounding Shadley.  Outlaw Dan “Dynamite Dick” Clifton was hit and wounded, but still able to ride.  Deputy Jim Masterson[3] tossed a stick of dynamite into where Arkansas Tom was hiding.  The explosion stunned Jones and he was taken into custody.

The Ingalls fight ended with the arrest of Murray and Jones.  Clifton and Newcomb were wounded, and Charley Pierce may have been wounded, but along with the other gang members these men managed to escape the law.  Shortly after the Ingalls encounter, Bill Dalton resigned from the Doolin gang to form his own.  On 23 May 1894, the Dalton gang robbed the First National Bank of Longview, Texas —it was the gang’s one and only robbery.  In June, a posse of six men under US Marshal Buck Garret of Ardmore, Oklahoma tracked Dalton to his home in Pooleville, Oklahoma.  Bill Dalton resisted arrest and more than 100 rounds were exchanged between the lawmen and the outlaw.  Eventually, gunfire subsided from the cabin and Bill Dalton was found dead with a gunshot to the head.  His body was shipped to California for burial.

Gratton Dalton

Grat Dalton idolized his older brother Frank, who was said to be the strongest of siblings and able to keep his younger brothers “in line.”  When Frank lost his life, Grat and Bob went to Fort Smith and applied for jobs as Deputy US Marshals.  Bob soon hired younger brother Emmett as a guard for prisoners and it was after this that Bob killed a man claiming self-defense.  But then Bob began drinking heavily and became what scholars call “restless.”  Bob took on the job of organized a police force in the Osage Nation, and he took along Emmett as his deputy.  Grat remained in Fort Smith.  Bob and Emmett maintained a good reputation at lawmen until around 1890 when they were implicated in stealing horses.  When stockmen organized a group to capture Bob and Emmett, the men fled to the Canadian River area southwest of Kingfisher, Oklahoma.  From there, they sent word to Grat that they needed his help.  He responded by arranging to provide them with horses, food, and ammunition.  Unhappily, Grat was discovered “aiding and abetting criminals” and was thrown in jail at Fort Smith.  He was the deputy who became a cellmate with a number of men who he’d arrested.  Grat was released a short time later, marshals believing that he would lead them to Bob and Emmett, however the two wanted men escaped by train to California.

Grat himself returned to California where he met up with Bill, Bob, and Emmett in January 1891 in San Luis Obispo.  It was after this that the Dalton gang formed, with Bob making plans to rob a train.  Cole, Littleton, and Bill attempted to dissuade them, but to no avail.  On the night of 6 February 1891, two masked men held up a Southern Pacific Railroad passenger train near Alila (present-day Earlimart), California.  No money was taken, but in the gunfire, one of the expressmen accidentally shot and killed the train fireman.  Since the holdup men were masked, no positive identity was ever established, but years later, Littleton affirmed that the robbers were Bob and Emmett.  Grat, who had taken to heavy drinking and gambling in Tulare, California, did not participate in the robbery.

Nevertheless, on 17 March 1891, the Tulare County Grand Jury indicted Bob, Emmett, Grat, and Bill Dalton for the Alila train robbery.  Bill and Grat were later arrested and placed in the county lockup and a bounty of $3,000 was placed on Bob and Emmett —both of whom were on the way back to the family home in Kingfisher, Oklahoma.  Bill made bail and promptly hired an attorney, who as it turned out, was as corrupt as Judas.  Despite testimony that Grat could not have participated in the robbery, owing to the fact that he was somewhere else, the power and might of the Southern Pacific Railroad won the day.  Neither Grat’s defense attorney or the prosecution mentioned the fact that the train fireman was accidentally killed by the expressman. Grat was found guilty and sentenced to life in prison.

During the night of 20 September, Grat and two other men escaped from the Tulare County Jail.  They left Bill behind, who in October had his day in court and was acquitted of the Alila train robbery.  Meanwhile, a joint posse under Tulare County Sheriff Gene Kay and John M. Hensley of Fresno County moved against the suspected location (later known as Dalton Mountain) of Grat Dalton and his accomplice Riley Dean near Sanger, California.  The posse ambushed Dalton and Dean as they were returning to their camp from a boar hunt.  Dean was captured, but Grat escaped while firing at the lawmen with his rifle.  After stealing a horse from a nearby ranch, Grat went to Livingston, California where he remained for several weeks.  With the assistance of Cole, he returned to Oklahoma and joined Bob and Emmett in their effort to assemble a new gang.

Survivor Emmett Dalton

Emmett Dalton was the eleventh child of the Dalton clan who lived near the town of Coffeyville, Kansas until around 1883 when the family moved to Indian (Oklahoma) territory.  As a youth, he worked as a stockman at the Bar-X-Bar Ranch and nearby Turkey Track Ranch.  Surrounded by fun-loving brothers and co-workers, Emmett seemed to “drift along” with everyone else, no matter what it was they wanted to do —no matter how reckless it was.  In time, Emmett joined his brothers as a deputy lawman and, by every account, he was conscientious in his duty.  In 1890, Emmett was arrested with his brother Bob for selling liquor to Osage Indians.  Eventually, charges against Emmett were dropped at a pre-trial hearing where it was established that the young man had not actually participated in the sale of the alcohol.  Bob was released on bail, but he never returned for trial.

By the summer of 1890, Emmett, Bob, and Grat were involved in stealing horses and selling them.  When word reached them that their horse-stealing was “well known” by almost everyone in the area, Bob and Emmett left for California.  Grat remained behind and was soon arrested but was later released owing to a lack of evidence.

It seemed that everyone in America was talking about the Dalton clan after 1889.  Newspaper stories about their “alleged” antics found their way into such faraway places as Pennsylvania.  The Dalton family may have been used as scapegoats for other bandits of the time, and whether the Dalton’s were involved or not, most people were prepared to believe, or preferred to believe, that the Dalton’s were responsible for train robberies in Wharton (8 May 1891), Lelieatte (15 September 1891), Red Rock (2 June 1892), and Adair (14 July 1892).  In later testimony, Emmett denied ever taking part in these robberies, and he might have been telling the truth (if one believes in fairies) —but, aside from the Wharton robbery, Emmett never denied that his brothers committed the other crimes.  He did say that Bob, “Blackface” Charlie Bryant[4], and “Bitter Creek” George Newcomb pulled the Wharton job.  According to writer Frank Latta, “Those Dalton boys must travel on the fastest trains to be able to bury their treasure in Indian Territory one week and rob a train here [in California] the next.  If a company of trappers were to be robbed at Hudson Bay tomorrow, the Dalton’s would get the credit.  While officers are chasing the Daltons, other highwaymen are committing robberies and stepping aside to watch the officers hunt the Daltons.”

Robert “Bob” Dalton

Bob Dalton was the sixth oldest of the Dalton family, born in 1863, the younger brother of Frank, whom he admired.  After Frank’s death, Bob and Grat were hired as deputy US Marshals at Fort Smith, Arkansas; Bob soon hired Emmett as a deputy/prison guard.  After Bob killed Charley Montgomery, who resisted arrest and fired first at Bob Dalton, Dalton began drinking heavily, became unhappy with his work, and looked forward to moving on in life.  He eventually resigned as a Deputy US marshal to accept a position as Chief of Police in the Osage Nation lands in Indian (Oklahoma) territory. Emmett went with Bob to the Osage Nation.  Both men were well-regarded by local citizens until the word got out that Bob and Emmett were involved in horse stealing in 1890.  Before they could be arrested, Bob and Emmett went into hiding in the bluffs of the Canadian River, seventy or so miles from their home in Kingfisher.  Bob and Emmett sent word to Grat they needed his help.  When Grat attempted to help them with food and horses, he was arrested and thrown into jail with the same men he’d arrested in the Oklahoma Territory. Authorities released Grat with the hope that he would lead them to Bob and Emmett, but Bob and Emmett proceeded to California without his assistance.

Grat eventually joined his brothers in California, and as already stated, was arrested and convicted for robbing a Southern Pacific train near Alila, California.  Although Bob, Emmett, Grat, and Bill Dalton were all named in the same Grand Jury indictment, neither Bill nor Grat participated in the Alila heist.  Bob and Emmett high-tailed it out of California.  Bill was arrested but later acquitted, and Grat made his escape from the county jail.  Years later, Littleton Dalton claimed that Bob and Emmet had told him on several occasions that they were the actual train robbers in Alila.  An innocent man was killed in the train robbery, shot accidentally by an expressman, and no money was stolen.  At this point, a good argument can be offered that the Dalton’s weren’t suited for a life of crime.

Dalton Gang Ends Abruptly

On the morning of 5 October 1892, Bob, Grat, and Emmett Dalton, Dick Broadwell and Bill Powers, calmly rode into the town of Coffeyville, Kansas.  The gang members had decided to rob not one, but two of the town’s banks, which were situated across the street from one another.  After tethering their horses in an alleyway more or less equidistant from the First National Bank and Condon Bank, the (not so cleverly) disguised gang members headed off to pull the job that would top anything the James gang ever did.  There was one small snag in the plan, however.  Coffeyville was the old hometown of the Dalton family and almost everyone in town knew the Dalton boys.  Moreover, everyone in town knew that the Dalton Gang were notorious outlaws.  Despite their disguises, townspeople recognized the Dalton’s and quickly passed the word: the Dalton’s were getting ready to rob the bank!

Bob and Emmett walked over to the First National Bank, while Grat, Dick, and Bill went to the Condon Bank.  As Bob and Emmett were busy stuffing grain sacks with cash, the townspeople were grabbing their guns and setting up an ambush.  When Bob and Emmett exited through the front door, they were met by a hail of bullets.  They rushed back inside and headed for the back door, but citizens were waiting for them there, as well.  Bob[5] was shot and killed, and although receiving twenty-three bullet wounds, Emmett survived and was taken into custody.

Condon Bank

In the Condon Bank, a cashier managed to delay Grat, Broadwell, and Powers with the concocted story that the vault was on a time lock and could not be opened.  This charade worked until a bullet came through the window of the bank and struck Broadwell in the arm.  Quickly scooping up around $1,500 in loose cash, the three men bolted out of the bank and fled down an alley.  A livery owner and local barber shot them to death.

Four local citizens also lost their lives in the gunfight at Coffeyville.  Emmett recovered from his wounds and was subsequently tried, convicted, and sentenced to life in prison.  After serving 14 years, the governor of Kansas granted him a pardon and Emmett went to live in California, where he became a Hollywood writer.  He passed away in 1937 at the age of 66 years.

At the time of their deaths, Bob Dalton was 23 years old; Bill Dalton was 27 years old; Grat Dalton was 31 years old.  The boys might have been audacious, but they weren’t very bright.

Frank Dalton, the lawman, lost his life in the performance of duty at the age of 29.

Sources:

1. Browning, J. A.  Violence Was No Stranger.  Barbed Wire Press, 1993
2. Latta, F.  Dalton Gang Days: From California to Coffeeville.  Bear State Books, 1976

Endnotes:

[1] The saloon owner, a man named Murray, later sued the federal government for damages to his property and person, but he lost the case due to Marshal Nix’s detailed testimony about what happened that day.

[2] On 29 November 1892, Marshal Hueston and Ford County, Kansas Sheriff Chalkey Beeson shot and killed Doolin-Dalton gang member Oliver Yantis.  We do not know if Arkansas Tom Jones specifically targeted Hueston during the Ingalls fight.

[3] Bat Masterson’s brother.

[4] So-called because of a gunpowder burn on the side of his face.

[5] Famed lawman Heck Thomas remembered Bob Dalton as the most accurate pistol shot he had ever seen, which proves that accurate fire is not always the final arbiter of lethal confrontations.