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Gentleman Bandit: The True Story of Black Bart, the Old West’s Most Infamous Stagecoach Robber

by John Boessenecker

When rumors of a stylishly dressed man robbing stagecoaches and leaving poems behind at the scene of the crime started to hit newspapers in the late 1800s, the culprit Charles “Black Bart” Boles became an instant cultural sensation. Set against the dusty, rugged backdrop of the Old West, Black Bart’s gentlemanly image still persists in pop culture today, arguably for its ability to transport us back in time to an overly romanticized version of American history when western expansion was thrilling and riches awaited anyone up for a little adventure. 

In many ways, Black Bart and the Old West in which he lived were both figures of fiction. 

Behind the veil of popular lore, however, what can be fact checked about the real Charles Boles’ life is actually far more interesting. Once a Lieutenant for the Union during the Civil War, Boles’ descent into stagecoach robbery as a means to quick riches can be read as an indication of the turbulent economic and social shifts of the time. America was now entering an era of rugged individualism, with the formalities of older eras thrown to the wayside, and Boles was leading the charge.  

Historian John Boessenecker is certainly not the first to turn a historian’s eye towards Black Bart, who in the past century or so since his prolific crime spree has accumulated a wealth of scholarship. What makes Boessenecker’s specific project fascinating, however, is the way in which he situates all these other texts next to each other in order to identify trends of exaggeration or misinformation. In doing so, Boessenecker identifies that the most interesting thing about Black Bart, actually, is the way in which we talk about Black Bart. 

“Most stage robbers were hardened, uncouth ruffians who stole the Wells Fargo box, the mail, and anything of value carried by the driver and his passengers. This mysterious bandit was unique, given his polite and gentlemanly demeanor and the fact that he never robbed anyone aboard the stage. Despite Hume’s relentless detective work, it would be long years and a total of twenty-nine stagecoach holdups before he finally discovered the true identity of the lone bandit. By that time, Black Bart would be the most notorious — and prolific — stage robber in American history.”

— John Boessenecker, author of Gentleman Bandit

The matter of the crime scene poems is likely a bit of fabrication, in Boessenecker’s opinion, fueled by an overly eager rumor mill willing to paint a portrait of Boles as an artist rather than a criminal. Still, there are some immensely pressing questions Boessenecker spends a great deal of time thinking about: 

Was it true that Wells Fargo paid him a salary to steer clear of their stage coaches after his days in San Quentin penitentiary, which several newspapers in San Francisco reported at the time? Was he really as nonviolent as he always adamantly claimed himself to be? And, most heartbreakingly, why did he spend so many years on the lam writing letters to his wife and children promising them he was on his way home, only to never live up to his word? 

The very real fact that no one really knows for certain what happened to Black Bart after his release from San Quentin has certainly done nothing to temper the air mystery surrounding his life. While Boessenecker covers all likely outcomes, even he has to admit we’ll likely never know the truth about where he met his end. 

Still, small moments of glimpsing the real Charles Boles beneath the legend he has been spun into are nuggets of historically crucial gold.

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