By Finn J.D. John • Offbeat Oregon • 

Gentleman, highway robber

Submitted photoCharles Bolton, aka Black Bart, as he appeared in the early 1880s.
Submitted photo
Charles Bolton, aka Black Bart, as he appeared in the early 1880s.
Submitted photoA poster 
for the 1948 B movie, “Black Bart.” Although the title character shares Black Bart’s real name, Charles Boles, the plot bears no resemblance to the real story.
Submitted photo
A poster for the 1948 B movie, “Black Bart.” Although the title character shares Black Bart’s real name, Charles Boles, the plot bears no resemblance to the real story.

Charles Bolton was a man with many friends. A charming, gentlemanly member of the social elite in the brand-new frontier town of San Francisco, he always had plenty of money. And if you asked him, he’d tell you he was the owner and manager of some mining concerns in the Sierra Nevadas, up near the Oregon border.

If you pressed for more details, he’d talk vaguely and change the subject, like a successful fisherman trying not to divulge the location of his favorite fishing hole. That was nothing unusual; plenty of successful mine operators were similarly cagey.

It also didn’t raise any eyebrows when Bolton left San Francisco for extended trips into the mountains, ranging in time from a few days to several weeks. Other mine owners did the same thing, going off to inspect their mining operations, making sure they weren’t being stolen from and maybe doing a little strategic prospecting too, or inspecting mines for possible purchase.

But Bolton was different. When he went off into the mountains, he didn’t bring a pick and gold pan. He brought a heavy ax – and a shotgun.

Charles Bolton was a stagecoach robber. In fact, he was, by some measure, the most successful stagecoach robber in history. His string of robberies lasted for over eight years – from July 1875 to November 1883.

Once safely out of sight from the city, Bolton would take off his gentlemanly attire and put on crude, homespun clothes and a stained-up linen duster. Like Lamont Cranston stepping out as The Shadow, Charles Bolton would transform into “Black Bart,” outlaw terror of the Oregon-California Wells Fargo stagecoach line.

Black Bart – he took the name from the villain of a popular dime novel – would promptly head for a rugged, wild place like the Siskiyou Mountains on the border between Oregon and California, moving quickly and quietly through the wilderness on foot. This was a major reason for his success: he was a master woodsman. Also, he knew that if he rode a horse or took a stagecoach, people would see him and possibly remember him afterward. Black Bart moved across the landscape like a fox, avoiding people and often traveling by moonlight.

The goal was to get to a spot where the stagecoach was most vulnerable – a steep, rocky incline overlooked by close trees and underbrush. The reason Black Bart liked the Siskiyous so much was that kind of terrain was common along the stage routes there.

After carefully scouting the stage road, Black Bart would carefully arrange some sticks to look like rifle barrels aimed at the road, then pull a flour sack over his head with eyeholes cut in it so he could see, and hide behind a bush with his shotgun and wait for the stage to come. When it did, he’d step out into the road and, with exquisite courtesy, ask if the driver would be so kind as to throw down the Wells Fargo strongbox and the mail sacks.

Over the years, that courtesy became a Black Bart trademark. He always said “please” and “thank you,” and he made a point of never bothering passengers. Several times, when frightened passengers tried to surrender their booty to him, he handed it back to them with urbane smoothness.

“It is Wells Fargo that I am robbing, not the passengers of this stage,” he told one woman as he handed her purse back to her.

Black Bart also became known as a poet, although not a very good one.

At several of his robberies, he left notes, including bits of doggerel (“I’ve labored long and hard for bread, for honor and for riches/ But on my corns too long you’ve tred(sic), you fine-haired sons of bitches”).

The express box was where the action was – that, and the mail sacks.

Most stagecoach robbers robbed the passengers as well, but Black Bart never did that; passengers, after all, were usually armed, and the last thing Bart wanted was a gunfight.

Once the box and the mail sacks were on the ground by the stage, Black Bart would motion the driver to move on, and then he’d get his ax out and break open the express box, take whatever was inside and be on his way – moving, usually, at top speed on foot through the densest possible brush for 12 to 24 hours, and leaving any trackers far behind, scratching their heads and wondering how he did it.

Oregon was farther away from Black Bart’s home base, but he made some of his most lucrative hauls from stages robbed on the Beaver State side of the pass. That’s because they were heading south – toward the gold fields instead of away from them – and therefore most stagecoach robbers figured they wouldn’t have any gold aboard. So they were so seldom robbed that it didn’t make sense to guard them heavily.

But one key part of Black Bart’s success was that he specifically targeted stagecoaches that would be carrying money rather than gold.

As an old miner himself – he’d been in on the Gold Rush in 1850 – Black Bart knew raw gold was dangerous. A good assayer could look at it and know what part of gold country it came from, and a stranger bringing in a big haul of gold from different regions would raise suspicions. Plus, it was always well guarded by men who expected robbery attempts, meaning it was a lot more likely that Bart would have to kill somebody – which he took considerable pains, on more than one occasion, to not do.

He also depended on stage drivers to cooperate with him, knowing his reputation as an easy robber. With Bart, you threw down the strongbox and you were on your way. Everybody knew this, and few drivers were willing to risk the wrath of his shotgun knowing that was all he wanted.

As time went by, Wells Fargo started chaining or bolting the express box to the coaches. This resulted in Black Bart having to climb up onto the stagecoach with shotgun and ax and batter his way into it, an activity that surely gave more than one driver a chance to get the drop on him; but that didn’t happen until that November day in 1883, when an armed rider came upon the stagecoach as Bart was trying to get into the box. The driver hastily borrowed the rider’s pistol and sent a bullet singing past Bart, who leaped from the stage and disappeared into the underbrush. Unfortunately for Black Bart, he left behind a bloody handkerchief – he’d cut his hand on the ax while attacking the express box with it. The handkerchief had a laundry mark and the Wells Fargo detectives lost little time in making the rounds of every laundry in San Francisco, asking whose it might be.

Eventually, the trail led the detectives to Charles Bolton. Asked if he was the notorious Black Bart, Bolton tried to bluff his way out with a haughty “Sir, I am a gentleman.” Alas, once detectives started looking closely at his financials, it was all over for Bolton – whose real name, as it turned out, was Charles Boles.

Boles drew an eight-year sentence for his crime. He was released in January 1888, and promptly disappeared. There are rumors that he tried to rob a stage in Nevada later that year and was shot dead; but nobody really knows.

(Sources: Yuskavitch, Jim. Outlaw Tales of Oregon. Helena, MT: Twodot, 2007; Hoeper, George. Black Bart: Boulevardier bandit. Fresno: Quill Driver, 1995;

Finn J.D. John is the author of “Wicked Portland,” a book about the dark side of Oregon’s metropolis in the 1890s. He produces a daily podcast at . To contact him or suggest a topic: or 541-357-2222.

Web Design & Web Development by LVSYS