Legends of the Old West - OUTLAWS Ep. 5 | “Burt Alvord”

Episode Date: May 20, 2026

In the closing days of the Old West era, Burt Alvord forms an outlaw gang to rob trains in southern Arizona Territory. As the constable of Willcox, Arizona he has the perfect cover story: he can plan the robbery and then make sure his fellow lawmen don’t catch the bandits. His idea works well the first time, but it hits a major roadblock the second time in the form of Wells Fargo express messenger Jeff Milton. In the town of Fairbank, near Tombstone, Jeff Milton fights Burt Alvord’s gang in one of the final train robberies of the Old West. Thanks to our sponsor, Quince! Use this link for Free Shipping and 365-day returns: Quince.com/lotow Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial. On YouTube, subscribe to LEGENDS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jeff Milton was a 38-year-old express messenger with Wells Fargo, and he was not supposed to work on February 15, 1900. Milton's job was to ride in the express car of trains on the Southern Pacific Railroad and guard safes and other valuables. The Wells Fargo agent, who was supposed to have been on the Southern Pacific run from Benson in Southern Arizona Territory to Nogales down by the Mexican border, had called in sick. The trip from Benson to Nagalis was a fairly straight shot, with only one stop in between at a town called Fairbank.

Milton hadn't been doing the job in Arizona for very long, but his reputation preceded him. He grew up in Florida during the Civil War and moved to Texas with his older sister and her husband in the late 1870s. He was in his latter teenage years, and he started by working at his sister's store in Navasota. Within a year or so, he was recruited. by the Texas Rangers. Jeff Milton was excited. He had heard stories of the famous Texas Rangers, but he soon learned that those stories were brief moments of action,

and the day-to-day life of a Ranger was not nearly as exciting as he imagined. But in April, 1881, right before his three-year enlistment ended, he finally received his taste of action. Milton and two other Rangers were in the West Texas town of Colorado City when they heard a commotion at a local saloon. Inside, the Rangers found two feuding ranchers. Milton was the junior man of the three Rangers, so he stood back while the other two Rangers tried to defuse the situation.

But when one of the adrenaline-fueled ranchers fired his pistol at one of the Rangers, Milton drew his own pistol without hesitation and returned fire. The rancher fell dead, and the feud ended. When Jeff Milton mustered out of the Rangers, he became deputy sheriff of Brewster County in southwest Texas. After a couple years, he drifted west to New Mexico territory, where he and a friend survived an ambush by three bandits. The bandits did not survive. Shortly afterward, he started a four-year run as a railway guard for the Southern Pacific Railroad. The job led him to become friends with the mayor of El Paso, Texas, who appointed Milton Chief of Police in

1894. A year later, Jeff Milton, as chief of police in El Paso, teamed up with a Texas Ranger and Deputy U.S. Marshal George Scarborough to take down notorious cattle rustler Martin Mrowse. By one account, Scarborough went down to Mexico to lure Mrow's out of hiding. When Scarborough coaxed the outlaw back to Texas, Milton and the Ranger sprung the trap. Mrow's didn't go quietly, and it took bullets from Milton and Scarborough to put down the outlaw. When the dust eventually settled after the killing and after George Scarborough had also killed John Selman, the man who had murdered infamous outlaw John Wesley Hardin,

Milton and Scarborough briefly teamed up as bounty hunters. The partnership didn't last more than a year or two, and by 1900, Jeff Milton was in Southern Arizona working for Wells Fargo as an express messenger on the Southern Pacific Railroad. His reputation as a fearless lawman and a dead shot with a gun was so well known that a gang of bandits had spent weeks doing reconnaissance to make sure Milton would not be on the train when they wanted to rob it in the town of Fairbank.

Their plan was already daring, and they didn't want to make it more challenging by going up against one of the toughest guards in the region. But on February 15, 1900, the guard who was supposed to work the run from Benson to Nogales, with a shortstop in the middle at Fairbank, called in sick. Jeff Milton took the guards place. When the train stopped at Fairbank

and the typical crowd of people at the station's platform moved toward the rail cars, Milton didn't know that five outlaws of Bert Alvord's gang were mixed in with the crowd, and the outlaws didn't know that the man they were specifically trying to avoid was in the express car. But Milden soon heard a commotion in the crowd, and then he saw men with guns using passengers as human shields. When he reached for the sawed-off shotgun near the door of the express car, one of the outlaws fired the first shot of the fight at Fairbank Station.

From Black Barrel Media, this is Legends of the Old West. I'm your host, Chris Wimmer, and this season we're telling stories of six outlaws. They're horse thieves, bank robbers, train robbers, and gunfighters. This is episode five. Bert Alvard, the Fairbank robbery. Bert Alvard had law enforcement experience like Jeff Milton, but Alvord's experience was not nearly as extensive or prestigious. Milton was from the East Coast and drifted west until he settled in Arizona.

Alvard was from the West Coast and made the shorter journey to Arizona because his father wanted to strike it rich in the boomtown of Tombstone. Albert was born in 1867, and his father Charles worked in the gold and silver mines in Northern California, before he, like many others, felt the irresistible pull of the silver strikes around Tombstone. Charles, his wife Lucinda, and their son Albert, who was usually called Bert, hurried to Southern Arizona during the early boom years of the 1870s. There have always been stories which say 14-year-old Bert Alford witnessed the legendary gunfight in a vacant lot on Fremont Street on October 26, 1881, which would later be mistaken.

known as the gunfight at the OK Corral. Even if Bert didn't see it, he was there for the buildup, the shootout, and the aftermath of one of the most famous events in American history. Four years later, when Bert was 18, he was in his own shootout in Tombstone, though it was far less dramatic. He got into an argument in a saloon with a man known as Six- Shooter Jim. Six-shooter Jim didn't pull his six-shooter fast enough, and he was shot and killed by Bert Alford. The killing must have been deemed self-defense because Burt was never charged with a crime. A year or so later, Burt moved away from what could have been a life on the outlaw trail to become a deputy for famed Cochise County Sheriff, Texas John Slaughter.

Bert Alvard's time as a deputy for Texas John was a mixed bag. Alvard chased cattle rustlers and learned to track and became pretty good at going undercover as a cowboy in saloons to catch a wanted man. But those saloons proved too enticing to ignore, whether he was on duty or off. He became a heavy drinker and gambler, which increasingly conflicted with his role as a deputy sheriff. In February of 1889, the bubble burst. Alvord was drinking in a tombstone saloon with two cowboys named Fuller and Fortino. When the saloon closed, the three men retired to a private house to keep drinking.

late in the night, Fortino insulted Fuller in some way. Fuller grabbed Deputy Alvord's gun and shot and killed Fortino. When Sheriff's slaughter arrived at the scene and learned that his deputy had been too drunk to stop the shooting, and that his deputy's gun was the murder weapon, he did not retain his deputy much longer. Bert Alvard moved seven miles west as the crow flies to the town of Fairbank. He was a constable in Fairbank for a few years before he moved north. to Wilcox in 1897. A year later, he was in a deadly confrontation with a cowboy named Billy King. Billy sounds like he was doing the typical cowboy hurrah. He got drunk, galloped his horse up and down

Main Street, and fired his gun in the air. Constable Alvard told Billy to stop, and they went into a nearby saloon to discuss Billy's infractions. Billy became threatening, and Alvard asked him to step into the back alley. When Billy walked through the back door of the saloon and turned around, Alvord shot him five times. It wasn't honorable, but no one cried over the loss of a no account like Billy King. And by that time, even though Bert Alvord still wore a badge, he wasn't viewed as much better. He was probably an alcoholic. He was barely holding on to his job, and he was becoming highly resentful of people who had money, which further eroded his dwindling interest in upholding the law. When he brought in an assistant,

whom he didn't really need, named Billy Stiles. Billy's primary job was to coordinate illegal activities for the gang that Bert Alvard was starting to assemble. Alvard had met some like-minded characters during his time as a quasi-lawman, and now he wanted his gang to commit a serious crime which would start changing his fortunes. With Billy Stiles, he added William Downing, Jack Dunlap, Tom Yois, Bob Brown, and two brothers, George and Lewis Owens.

Through Alvard's official contacts, he learned that a safe on a Southern Pacific train on September 9, 1899, was going to contain a lot of money. Alvard made a plan for his gang to rob the train when it stopped in the village of Cochise, 10 miles west of Wilcox. On the night of September 9, 1899, Alvard's gang rushed onto the train at Cochies, forced the crew to decouple the locomotive and the express car from the passenger cars, and drive the express car farther down the tracks. The bandits blew the safe open with dynamite, grabbed between $3,000 and $10,000 in cash, and fled about 30 miles west to the Chiricawa Mountains

where they hid at William Downing's ranch. Crucially, Constable Bert Alvord did not participate in the holdup. His alibi had to be carefully staged. While the robbery unfolded at Cochies, he sat in a saloon in Wilcox, playing cards, drinking, and ensuring plenty of witnesses saw him. When news of the holdup arrived, he reacted with loud outrage and immediately joined the posse of Sheriff Scott White to pursue the bandits.

And, no doubt, Constable Alvord expressed great dismay when the posse failed to find the robbers. The heist was an easy success. Alvard had planned it perfectly, and his gang had executed it flawlessly. Alvard felt emboldened, and he wanted to do it again. By October of 1899, the dust had settled from the September robbery, and Alvord started working on a new job. It was an audacious idea, not because of the size of the gang or the complexity of the plan, but because of the location. He wanted to rob the train right there at the station in Fairbank, Arizona.

The reason for targeting Fairbank was simple. It was the main railhead for Tombstone. The peak years of Tombstone's silver boom were long gone, but, but there was still plenty of money flowing in and out of town. Anything shipped by train to or from Tombstone went through Fairbank. By robbing the train at the Fairbank station, the gang could take it all, money and valuables going into town and money and valuables going out of town. It was audacious and also crazy and greedy.

The gang could have stopped the train in a lonely stretch of desert like they had done with the Cochee's robbery and conducted the heist with relatively little effort. Following the tracks of the Southern Pacific Railway out of Wilcox, where Alvord and the gang were headquartered, the train rolled through the village of Cochees, then wound its way through the desert to Benson. From Benson, the train made a hard turn south and moved through 18 miles of mostly raw desert before it stopped at Fairbank. Anywhere between Benson and Fairbank would have worked, and anywhere between Fairbank and Nogales would have worked. But Alvord wanted his crew to rob the train in Fairbank. His men would be dressed like ordinary cowboys, and they would blend in with the

other people on the platform. The bandits would use the civilians as human shields to force the train guards to give up the money without any trouble. The outlaws hoped shock and speed would offset the public location and the fact that they couldn't wear masks while trying to blend in. And the plan relied heavily on one more critical element. Wells Fargo Express Messenger Jeff Milton could not be working that day. No one wanted to tangle with a guard of his well-earned reputation, and Billy Stiles went to great lengths to learn Milton's schedule. As Alvard and Stiles closed in on the Target Day, February 15, 1900, they confirmed that Milton was not supposed to work that day. In that respect, they were right. He wasn't supposed to work. But the plan was already set when Jeff Milton received a

telegram informing him that he needed to work that night. The guard who was supposed to to work the run from Benson to Nogales was sick and Milton needed to fill in. Jeff Milton, with his sawed-off shotgun, was about to add the most famous notch to his legacy. On the evening of February 15, 1900, people crowded onto the platform at the Fairbank train station. Some waited to board the train. Some waited for friends or family members to exit the train. And some waited for packages to be offloaded from the Wells Fargo Express car. In the crowd, dressed as average everyday cowboys, were five members of Bert Alvord's gang. Jack Dunlap, Tom Yose, Bob Brown, George Owens, and Lewis Owens.

Like the Cochee's train robbery five months earlier, the planners, Bert Alvard and Billy Stiles, were not present. Their roles were the same as in the previous robbery. They would act surprised about the heist and try to steer the investigation away from the bandits. When the train stopped at the platform, the brakes squealed, steam hissed from the locomotive, and the passengers started to debaward. Wells Fargo Express Messenger Jeff Milton slid open the door of the express car and started to hand packages down to the station agent on the platform. At that moment, the five outlaws in the crowd started the robbery.

One moved toward the locomotive to grab the engineer. The other four converged on the express car. They trained their rifles on Jeff Milton, whom they would have recognized. He wasn't supposed to be there, but it was too late to worry about that now. The bandits used people on the platform as human shields, and one of the robbers shouted at Milton to put up his hands. At the same time, the bandit issued the command, one of the outlaws fired his rifle. The bullet knocked the hat off of Jeff Milton's head. On instinct, Milton grabbed a sod-off shotgun that was next to the open door of the express car. car, but he knew he couldn't use it. If he fired at the bandits, he would hit the innocent people around them. His pistol was behind him on the desk inside the car. For that terrible moment, he was stuck. It only lasted a fraction of a second, but that was also the pace at which the problem was escalating. All the outlaws opened fire and started blasting the express car. Several bullets pounded Milton's left arm between his shoulder and his elbow. The shots spun him

around and knocked him to the floor of the car. The bandits thought they had killed Milton, or at least neutralized him. They rushed to the car and jumped up into the doorway to start stealing money. That gave Milton a clean shot. Lying on the floor of the car, he raised the sawed-off shotgun, sometimes identified as a short barrel 10-gauge, and pulled the trigger. Jack Dunlap took most of the blast. And if the weapon really was a short-barrel 10-gauge, then it's a wonder Jack lap wasn't cut in half by the blast at close range. The shot prompted the other three outlaws to leap out of the express car. Jeff Milton's arm was bleeding badly. Later reports say a bullet cut an artery. With blood pouring from his wounds, he kicked the door of the express car closed and

threw the keys to the safe into a pile of packages. He tore up the sleeve of his shirt, fashioned it into a crude tourniquet for his severely wounded arm, and passed out. Outside, the outlaws fired a barrage into the express car to try to kill Milton, but all of their shots missed. The robbers used the engineer as a human shield, threw open the door, and re-entered the express car. Jack Dunlap lay near the door, and Jeff Milton lay farther back in the car. One of the outlaws was about to shoot Milton, but the engineer convinced the bandit that Milton was dead. The robbers couldn't find the keys to the safe, and the robbery had already turned into a nightmare, so they scrounged about $40 in coins from the express car and fled.

They grabbed Jack Dunlap, who was still alive, threw him onto his horse, and galloped out of Fairbank. Behind them, the townspeople scrambled to help Jeff Milton. They rushed him 18 miles north to Benson, where a special train hurried him to a hospital in Tucson. For Jeff Milton and for the gang, the next few hours would be crucial for survival. While the people of Fairbank were trying to save Jeff Milton's life, the five train robbers were galloping into the desert. Jack Dunlap was horribly wounded and slowing the escape, so the other four outlaws left him behind on the trail and rode away.

A posse from Tombstone found Jack a short time later. He was still alive and he was mad about being left behind. He survived for a few days, and during that time he named the other four bandits and the planners, Bert Alvard and Billy Stiles. After those revelations, simultaneous and opposite stories flew through Cochee's County.

The first was the story of the heroic actions of Jeff Milton, who had single-handedly faced down a gang of bandits and was badly wounded in the process. A doctor in Tombstone performed emergency surgery on Milton's arm, but the crude operation wasn't enough.

Within a couple days, the doctor put Milton on a train to San Francisco to get specialty treatment. The second story was the shocking announcement that Lawmen had planned the Fairbank robbery and the Cochee's robbery. Before Bert Alvart and his gang could take evasive action,

they were all arrested and thrown in jail in Tombstone. There, Billy Stiles agreed to testify against his comrades in exchange for his freedom. But that seemed to be part of a larger plan, at least for Billy and Bert Alvard. Billy was released from jail, and he returned to Tombstone two months later. On April 7, 1900, he visited Alvard in jail.

At the end of the visit, Billy got into a fight with the deputy who was on guard duty, and the fight was probably intentional. During the tussle, Billy shot the deputy in the leg and then opened Alvard's cell. Billy and Bert fled Tombstone and ran south to Mexico. For the next two years, Billy Stiles stayed near the border, and Bert Alvard went deeper into northern Mexico, into the Sierra Madre Mountains, which was also the stronghold of a far more deadly and notorious outlaw, Augustine Chaconne. In 1902, Bert Mossman, the first captain of the Arizona Rangers, a group similar to the famous

Texas Rangers, dedicated himself to capturing Chacon. To do so, he planned to use Billy Stiles and Bert Alvard to lure the outlaw out of his fortress in the Sierra Madres. Over the course of four months, from January to April, Mossman found Stiles down along the border and persuaded him to join the effort. In return, Billy would receive some of the reward money when Chaconne was caught, and Mossman would testify to Billy's important role. In April 1902, Billy went down to Mexico, found Bert Alvert, and persuaded him to help based on the incentive that the robbery charges would be erased by a judge who was working with Captain Mossman. Alvert agreed to the plan, and in September of 1902, Bert Alvard, Billy Stiles, and Captain Mossman

successfully captured Augustine Chaconne. Two months later, Chaconne was hanged for robbery and murder. The next month in December 1902, Captain Mossman made good on his promises, and Cochee's County dropped the train robbery charges against Bert Alvert. Albert was a free man again, like Stiles, but their freedom only lasted seven months. In July 1903, U.S. Marshal Myron McCord filed federal charges of mail robbery against Alvard and Stiles.

The marshals arrested Alvard and Stiles and threw them back in jail in Tombstone. They spent the second half of 1903 in jail awaiting their fates, which were announced on December 8th. They would spend two years in Yuma Territorial Prison. Nine days later, Bert Alvard and Billy Stiles escaped the Tombstone Jail. Bert Alvord and Billy Stiles ran back to Mexico. Six weeks later, on February 6, 1904, they committed a robbery in Mexico,

and two weeks after that, the Arizona Rangers went down to Mexico to get them. The Rangers confronted the two fugitives near the town of Naco, and the two groups exchanged gunshots. Bert Alvard sustained a minor wound, but it was enough to slow him down so that the Rangers could capture him. Billy Stiles escaped and stayed on the run. The Rangers took Alvard back to Arizona and installed him in the Tombstone Jail once again. That time, he stayed. His gang was gone, they were dead or scattered, and there was no one left to help him break out.

From the Tombstone Jail, he was transferred to Yuma Prison to serve the sentence he had received two months earlier. He completed his sentence on October 9, 1905, two weeks ahead of his scheduled release date. Prison authorities did not provide a reason for his early release, but a little bit of favoritism was the suspected explanation. Three weeks before Alvard walked out of prison, Mexican authorities sent an arrest warrant to the U.S. Marshal of Arizona territory. Mexico wanted Alvard for the robbery he had committed right before he was caught by the Arizona Rangers. By releasing Alvert early, it gave him a chance to leave Arizona and dodge the warrant,

which he did immediately. Bert Alvard took a train west to Los Angeles and stayed with his sister for a short time. From there, he took a ship to Panama and worked on the construction of the Panama Canal at the end of 1905. After that, he disappeared from the historical record, save for one last entry. The final piece of Bert Alvard's story was known only from a short article. in the Graham Guardian newspaper from Safford, Arizona. The article was dated July 29, 1910. It referred to a letter that was sent to a friend of Alvards in Los Angeles.

The letter notified the friend that Bert Alvard had died on the island of Barbados. Alvard had been working on a railroad project in the Amazon jungle in Brazil when he contracted yellow fever and was transported to Barbados for treatment. Based on the dates associated with the newspaper article, it would appear Bert Alvard passed away at 43 years old from yellow fever in March or April of 1910, though there is at least one account which says it could have been as early as November 1909. Either way, Bert Alvord's story was a strange one. He was a kid who might have witnessed the gunfight at the OK corral. He was a decent but not great deputy sheriff and then a corrupt constable.

He was the leader of a gang which committed two train robberies. One was a perfect success, the other was a spectacular failure. He was a two-time escapee from the Tombstone Jail, a fugitive and a thief in Mexico who also helped catch one of the most notorious outlaws in the Southwest, and then he was a construction worker in South America. There weren't many outlaws of the Old West who could boast such a wide variety of roles on their resumes. His lieutenant, Billy Stiles, was along for many of the

adventures, but his story disappeared into the shadows of history after he and Alvard were confronted by the Arizona Rangers in Mexico in 1904. Billy escaped the confrontation, and there is no conclusive proof as to where he went, what he did, or how long he lived. And finally, Jeff Milton, the Wells Fargo Express Messenger who fought the gang during the Fairbank train robbery, survived his severe gunshot wounds. By the time he made it from the hospital, in Tucson to the hospital in San Francisco in February of 1900, his wounded left arm was infected and swollen. For a while, it looked like the doctors would have to amputate, but they didn't. In a similar situation to Virgil Earp, Wyatt's older brother, whose arm was mangled by shotgun

blast during an ambush two months after the gunfight at the O.K. Corral, Jeff Milton never recovered the use of his arm. Despite that limitation, again, like Virgil Earp, Milton continued to serve as a lawman. A little more than a year after his life-threatening injury, he joined the Bureau of Immigration and served as a Border Patrol agent for the next 28 years. When he retired in 1932 at the age of 70, he settled in Tombstone, where he lived with his wife until he passed away in 1947 at the age of 86. Next time on Legends of the Old West, it's a pure outlaw story. Bill Longley was a wandering killer from Austin County, Texas. Like fellow Texas killer John Wesley Hardin, he told fantastical stories about

his exploits, but he still murdered at least seven people and maybe many more during his four-year heyday in the mid-1870s. That story is next week on Legends of the Old West. To binge all the episodes of a new season and to listen to every episode of the podcast with no commercials, subscribe in Apple Podcasts or sign up through the link in the show notes or on our website, blackbarrelmedia.com. This series was researched by Mandy Wimmer and written by me, Chris Wimmer. Original music by Rob Villeer.

Thanks for listening.