The Dalton Gang’s Final, Doomed Heists in the Twilight of the Old West

In February 1891, hoping to help his brothers find steady work, Bill Dalton wrote a letter to the superintendent of the nearby Muller and Lux Ranch, having heard it was hiring. After that was confirmed, Bill borrowed a horse and saddle from one of his hired men for Grat and two saddles from his neighbors for Bob and Emmett. The three left, telling Bill they were headed to their new jobs at the ranch. No doubt Bill stopped congratulating himself the next day when he discovered that his brothers had made a trapdoor out of the ceiling in the closet of his house to get into the attic. Most likely, he did not tell his wife, Jane, that this implied his brothers would be back.

Still, it was possible that Grat, Bob, and Emmett intended to give the Muller and Lux jobs a try. They made their first stop in Cholame, where they watered their horses, got drinks, and, just in case there was a dry stretch of road, bought a flask of whiskey. They then pushed on, but somewhere along the way, their thoughts, perhaps influenced by the whiskey, turned away from finding work and toward what could be easier money. They came up with a rather convoluted way to get it.

The first step was to find a better horse than the nag Bill had borrowed for Grat. When the three brothers reached Malaga, about four miles south of Fresno, Emmett remained there while Grat and Bob kept riding fifteen miles northeast to the ranch of Clovis Cole, where Lit had been working. Before arriving, though, Bob rode back to Malaga with Grat’s horse in tow, to make it appear as if Grat had walked all the way to the Cole spread.

“I was asleep in the bunk house when I heard a single knock outside my bunk,” Lit recalled. “The knock was repeated twice, about a half minute apart. This was a signal we brothers had used among us for many years. So I knew that one of the boys was outside and that he needed help.” It was Grat, and he “had a fishy story.”

Grat claimed that his horse had gone lame and that he had walked the rest of the way from Malaga, where the boys were waiting, to see if Lit could furnish him with a fresh horse. Ironically, a stranger might have obliged, but Lit knew his brothers and, suspecting that Grat was up to no good, he refused to lend one of his boss’s horses. Instead, he borrowed a rig and drove Grat back to Malaga, apparently hoping he could find out what the other Daltons were up to and, if necessary, talk them out of it.

Bob and Emmett were killing time in a ranch barn a mile west of Malaga, and after Grat and Lit joined them, they talked until morning. Lit offered to help Grat sell his horse so he would have some money. He did so but could get only sixty dollars for it. Lit returned to the Cole Ranch, and Bob and Emmett rode off, leaving an irritable Grat behind.

He was not alone long. After contemplating his few options, Grat hoisted his saddle and took a train to Traver, where he caught up to Bob and Emmett. The reunited brothers played poker all night there and then traveled to Tulare to do the same. (We have to assume that Grat rode with Bob or Emmett, whichever had the more durable horse.) Along the way, the Daltons asked about the Southern Pacific Railroad pay car that routinely made its way down the valley from Oakland to Bakersfield. This train’s arrival was always accompanied by a crowd of gamblers and prostitutes looking to make money off the recently paid employees. An idea was hatched.

The next stop for the three brothers was Delano, where they spent their time at the saloons. They all used assumed names, even though several men had recognized Bob and Grat from the days when they would travel with their father’s racehorses and from when they used to gamble and get in bar fights in Tulare. Grat also kept his distance from Bob and Emmett, pretending to not know them, and slept and ate in different places from them because he felt he was too easily recognizable. The reason for such subterfuge was they had decided to rob the next Southern Pacific train with a pay car attached—though they kept getting into bar fights, which was not the best way to go unnoticed.

The trio of would-be bandits became a duo when Grat lost his remaining cash playing cards. Broke, and with his brothers unable to stake him to anything, he gave up on trying to buy a new horse. He thus missed out on the crime . . . though he would still wind up paying a price for it.

In Delano the morning before the robbery, Bob and Emmett had several drinks, bought fifteen sandwiches wrapped in newspaper, and two quarts of whiskey. Thus fortified by 10:00 a.m., the two brothers rode toward Alila, one of the train’s stops. Taking advantage of the shade in a secluded spot a half mile outside of the town, they ate half their lunch and emptied one of the whiskey bottles. That night, probably a bit woozy in their saddles, Bob and Emmett rode to the Southern Pacific line.

They tied their horses to a telegraph pole and walked up the tracks to Alila. When the train pulled into the station, the brothers snuck aboard the baggage car. Once the train got underway, they made their way to the engine compartment. They aimed their revolvers at the fireman, George Radliff, and the engineer, Joe Thorne, and ordered them to stop the train.

Clearly a rookie train robber, Bob wore a mask made of a white handkerchief that kept getting in his eyes, and to be able to see clearly, he pulled the mask down around his neck. As he did so, the fireman opened the door to the firebox and in the bright light was able to get a good look at Bob. Emmett smacked the fireman over the head with his revolver and ordered him to close the door, which he did. 

The train came to a halt just fifty yards from where the robbers’ horses were tied. Bob and Emmett marched the engineer and fireman down the side of the train to the express car. The expressman, C. C. Haswell, took a look out the door and could see the group coming. He quickly put out the car lights and locked the door and windows. Just then, the brakeman walked up with a lantern to see what was happening, and Bob took it from him.

With the light from the lantern, Emmett thought he could see a man through the glass window of the express car. He told Bob, who then began firing through the window. Immediately afterward, Haswell rested his revolver on the windowsill and fired the gun until it was empty. Then Bob resumed firing his reloaded pistol into the car. One of the bullets ricocheted off a steel bar by the window and grazed Haswell’s forehead. As soon as Bob’s gun emptied, Emmett began to shoot.

During all the firing, Radliff, the fireman, turned and ran. Emmett tried to shoot him and at first thought he had succeeded when Radliff stumbled and collapsed. He was indeed mortally wounded, but it would later be determined that he had been hit by one of Haswell’s bullets. Unfortunately for the Daltons, they would be blamed in the subsequent newspaper accounts.

The expressman was not about to budge. He reloaded his gun, got down on the floor, and lay quiet. Bob and Emmett yelled and swore at him, but after several minutes, when there was no response, they concluded that Haswell was dead. And for all that, they were not any closer to the inside of the pay car. The brothers hurried to their horses, untied them, and took off. As they did so, Bob fired at a deputy sheriff, who had taken his sweet time getting off the train to see what all the commotion was about.

As they rode away from the scene, Bob and Emmett accused each other of shooting the fireman. They headed west but soon became lost in the darkness and thick fog around Tulare Lake. After the sun rose and the fog lifted, the two were able to ride in the direction of the Estrella River and Bill’s ranch, along the way using back roads and resting in secluded spots. When they finally arrived, they noticed that Bill’s buckboard was gone and that there was a strange rig beside the corral. Afraid to go inside, they instead went to the ranch of Bill’s father-in-law, Cyrus Bliven, where they learned that Bill had been out looking for them, having heard of the Alila incident.

Back in Alila, after the attempted robbery, the Tulare County sheriff, Eugene Kay, had been able to discern the horse tracks going west from where the train had stopped, but he lost them in the thick fog. After taking measurements and sketches of horse and boot tracks and finding a piece of wood that appeared to have broken off a stirrup, Kay, with his deputy, Jim Ford, set off in pursuit.

“The most remarkable exploit of Kay’s whole career as sheriff was the pursuit of Bob and Emmett Dalton,” declares Frank Latta. “It might also be stated with little fear of dispute that it was one of the most remarkable pursuits of criminals ever waged by a determined officer of the law. It began at Visalia, extended through seven western states and a portion of Old Mexico, blazed a trail six thousand miles in length by every existing means of transportation, and lasted more than three months.”

Days later, the two lawmen, driving a rig and having been guided by people who had spotted two horsemen, and with the sun soon to set, arrived at a farmhouse. They had not seen any tracks since leaving the hills and wondered if they had wandered off the route of the outlaws. Sheriff Kay knocked on the ranch door and was met by a woman with her two children. She told him that her husband wouldn’t be home until late but that they would be welcome to stay the night. Kay and his deputy left their rig beside the corral and went inside for the dinner Jane Dalton offered them.

It was after dark when her husband, Bill Dalton, got to his father-in-law’s ranch. He loaded Bob and Emmett into his rig and returned to his farm. Bill also had no idea who the buggy beside the corral belonged to, so he told the boys to sleep in the straw haystack next to the barn while he went inside alone. Bill did not know Kay or his deputy, who did not reveal themselves as officers, and that made him nervous.

They talked for an hour, and then, continuing to be calm under pressure, Bill offered them the spare bedroom. Moments after the visitors accepted and went to bed down for the night, Bill rushed out and warned his fugitive brothers to stay clear of the house.

The next morning, while getting their rig ready to ride, Sheriff Kay thought he would express his thanks to Bill and his wife by giving their barn a quick cleaning. As he began forking the manure pile out of the barn, he found the remnants of a saddle buried in it. The moisture from the manure had not penetrated the leather, so he knew it had been placed there recently. Kay saw that the saddle had a piece of wood broken from the stirrup. He took out the piece of hardwood they had found near Alila and noticed it was a perfect match. Kay then began to suspect that his host may in fact be associated with the robbers—and might even be one of the robbers himself. Kay put the saddle in his buggy, and he and his deputy left. 

The suspicious sheriff spent the day learning what he could about the Daltons. He discovered that there were five brothers in the area, and three of them were regulars in the local saloons. Bill and Lit, however, seemed to have good reputations. Kay then received a telegram from Tulare and learned that three men had gambled from Traver to Delano for three days before the robbery following the Southern Pacific pay car. This was not unusual, but one of the gamblers was positively identified as Grat Dalton. The deputy, Jim Ford, now recalled that he had played cards with Grat and brothers Bob and Emmett while they were in Tulare.

While Kay was in Paso Robles, he was joined by a Southern Pacific Railroad detective, Will Smith, and the San Luis Obispo County sheriff, E. F. O’Neal. They discussed what Kay had learned, and it was decided to assemble a posse and that night surround and search Bill Dalton’s farmhouse. Then there was a glitch: Anxious to collect the probable reward or simply impatient, Smith and O’Neal rode out to the Dalton place before sundown.

When the two lawmen arrived, Bill recognized both of them. This was when the trapdoor came in handy, because Bob and Emmett used it while their brother went outside to greet Smith and O’Neal. There was a bed in the attic, and both Bob and Emmett lay quiet with their six-shooters aimed at the trapdoor. Taxing Bill’s fortitude as well as his hospitality, the sheriff asked if they could stay the night. While he and Bill put the horses in the barn, Will Smith immediately went in the house and began questioning Jane Dalton.

She told him that Bob and Emmett had gone to Seattle. When Bill entered, he and Smith got into an argument about the latter confronting his wife and children. O’Neal walked in during the middle of the shouting and tended to agree with Bill. The sheriff spotted a guitar, and trying to change the subject, he asked Bill if he would play for them. This suited Bill perfectly, as he was a skilled guitar player and needed to drown out any noise his brothers might make. Bill sang and played guitar until midnight, while Bob and Emmett lay in the attic afraid to move and probably getting pretty sick of hearing their brother’s voice.

According to Lit, “Bob told me afterward that if Will Smith had put his head through that trap door he would have stopped two .44-caliber bullets before he could have batted an eye.”

Finally, the lawmen went to bed. That was good news, but the bad news was they didn’t leave until after 10:00 a.m. Bob and Emmett had spent way more time in the small, stuffy attic than they cared to. Smith and O’Neal returned to Paso Robles and reported to Kay that there were no suspects at the Dalton farm and Bill had not been involved in the Alila incident.

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From The Last Outlaws by Tom Clavin. Copyright © 2023 by the author and reprinted by permission of St. Martin’s Publishing Group.