'Shotguns and Stagecoaches' reveals how Black Bart conducted heists in Sonoma, Mendocino counties

He was the most prolific stagecoach robber in American history, a gentleman bandit who never shot anyone, didn't rob the passengers and even said “please” when he ordered the driver to hand over the “treasure box.”

Charles E. Boles, better known as Black Bart, held up more stagecoaches than anyone else - 29 - including robberies he committed in Sonoma and Mendocino counties in the late 1870s and early 1880s.

He was known as the “Poet Highwayman,” stemming from doggerel he left at a couple of his crime scenes, including near Fort Ross, where, in the summer of 1877, he robbed the stagecoach traveling from Point Arena to Duncans Mills.

The verse he left behind scribbled on a Wells Fargo waybill taunted authorities and became part of Western lore:

“I've labored long and hard for bread

For honor and for riches

But on my corns too long you've tred

You fine haired Sons of Bitches.”

It was signed “Black Bart, the Po8,” (as in poet)

It would be six years and a couple of dozen more robberies before lawmen finally caught up with Black Bart, the result of a telltale laundry mark left on a dirty, white silk handkerchief at the scene of his last holdup in Calaveras County.

Detectives were able to trace it to one of more than 90 laundries in San Francisco at the time and link it to Boles, an elegantly dressed man in his early 50s, with bright blue eyes and a large gray mustache who posed as a mine owner.

Because he didn't drink, gamble or consort with prostitutes, Boles' true calling was never suspected, according to John Boessenecker, author of “Shotguns and Stagecoaches, the Brave Men who rode for Wells Fargo in the Wild West.”

Boles, his double life as Black Bart and his capture, take up a chapter in the latest book by Boessenecker, a New York Times best-selling author, Bay Area lawyer and former police officer who is considered a leading authority on crime and law enforcement in the Old West.

Boles' exploits and his arrest by former Alameda County sheriff and private investigator Harry Morse are among the intriguing characters profiled in the book. It portrays the valiant shotgun riders and detectives who protected Wells Fargo shipments of gold, silver and currency, as well as a rogues' roster of highwaymen and robbers who held up the stagecoaches and trains.

Before Black Bart committed eight separate stagecoach robberies along the isolated roads of Sonoma and Mendocino counties, there was a gang of stagecoach bandits that worked the main road from Healdsburg to Ukiah in 1871.

They were known as the Houx Gang and consisted of John Houx, “Big Foot” Andrews, Lodi Brown and Rattle Jack.

Rattle Jack and a stagecoach passenger were killed in an exchange of gunfire during their fourth holdup near Asti, south of Cloverdale, and several other passengers were wounded. The gang committed six robberies by the time they were caught with the help of a Wells Fargo agent who went undercover.

That agent, Steve Venard, had already made headlines across the country from a shootout he had five years before with a criminal gang that was running amok, near Nevada City, holding up stagecoaches and travelers. He singlehandedly shot dead three of the bandits with his Henry rifle in a running gun battle along the south fork of the Yuba River.

On his subsequent assignment in Sonoma County, Venard dressed in rough clothes. He told people his name was Jones, and he was looking to buy a hog ranch.

He spent most of his time in the saloons and gambling halls of Healdsburg, Cloverdale and Ukiah, drinking and playing cards and making a point to befriend the robbery suspects - Houx and his companions - according to Boessenker's account.

When the villains were drunk, they talked too much, boasting of their exploits and plans for more stickups, which led to their undoing.

Black Bart, or Boles, was another matter entirely, precisely because he was not a ruffian like the usual stage robbers. And he acted alone.

“He clearly loved the good life he lived in San Francisco, pretty much the whole time he was a stage robber,” Boesseneker said in an interview. “He would leave the city just to do robberies. He didn't like to live outdoors.”

Well-spoken, and well-dressed, Boles would transform into his Black Bart alter ego in stage robberies that played out in 10 Northern California counties and one in southern Oregon.

To rob a stage in Mendocino County, Bart would have taken a boat or ferry before boarding the San Francisco & North Pacific Railroad at Sausalito, traveling to the railroad's terminus at Cloverdale, according to Bruce Levene , author of “Black Bart - The True Story of the World's Most Famous Stagecoach Robber.” Only stages went farther north beyond Cloverdale.

Black Bart's modus operandi was to don a white cloth sack over his head, showing only two holes for his eyes. He would typically meet a stagecoach with a shotgun as the horses labored up a hill, making it easy to step into the road and take over the reins.

Bart was careful not to rob stagecoaches accompanied by shotgun “messengers,” or guards, which had the most valuable shipments. So he never made a really big haul.

But, at a time when the average police officer made about $80 a month, according to Boessenecker, most of his robberies netted between $500 and $2,000, by making off with the locked strongbox beneath the driver's seat which could contain shipments of gold, gold dust, cash and small valuables.

One of the more remarkable things about Black Bart is that he didn't travel by horse, but walked hundreds of miles. In an era when it was often easier to give a description of the horse than the rider, the bandit on foot could be tougher to track.

“He would break his shotgun down, put it in a bedroll and walk over mountains. He didn't follow roads,” Boessenecker said. “He would easily walk 100 miles in a few days. He was a fantastic walker. That's well documented.”

Boessenecker, who became fascinated with the Old West watching TV westerns as a kid, has been researching the topic for more than 50 years, tracking down primary sources in letters, libraries, courthouses, census and genealogy records, and in old newspaper accounts. He has twice been named Best Nonfiction Writer by True West magazine and has appeared as a historical commentator on PBS, the History Channel, A&E, and other networks.

Boessenecker cautions that as much as one-third to one-half the material about Black Bart on some websites is fictitious.

What is known about Boles is that he was born in England around 1829, and his family came to the United States when he was 2, settling in Jefferson County, New York. In 1850, he and his brother joined the California Gold Rush.

A few years later, he returned East, married and settled in Decatur, Illinois. During the Civil War, he enlisted on the side of the Union, fought with distinction in major civil war battles and attained the rank of sergeant before suffering severe wounds in 1864.

After the war, he left his wife and four children behind to join the gold rush to Montana, and they never saw him again.

Boles drifted through mining camps in Montana, Idaho and Utah before he returned to California. He sent letters to his wife, promising to return home, while she eked out a living as a seamstress in near poverty with her children.

By 1875, Boles was living in San Francisco. When he was arrested eight years later after his extensive secret career as a stagecoach robber, there was a woman, perhaps a mistress, who tried to visit him in jail, according to Boessenecker.

Boles ended up being convicted and sent to San Quentin, but got out early for good behavior after serving four years. He disappeared and was never seen, nor heard from again, his whereabouts an enduring mystery of the Old West.