May 13—While growing up in the hamlet of Plessis in the town of Alexandria in the 1800s, Charles E. Boles realized one fact that would become the first building block in creating the attributes of a deceitful rascal and a notorious thief who holds an infamous record.

He hated to farm.

Mr. Boles had several more experiences that would later benefit his life of crime and becoming America's greatest stage coach robber — from seeking his fortune in the California gold rush to honorably serving the Union in the Civil War, with some heroics. Later, along the way as he robbed, Mr. Boles developed a reputation as the best-behaved crook in the Old West. He held up stages with polite demands, stealing from Wells Fargo express stages and the U.S. Mail, but never robbing a passenger. He became known as "The Gentleman Bandit" and lived a second life as a genteel man-about-town in San Francisco.

There has been lots of folklore and mythology related to the life of Mr. Boles, but New York Times-bestselling author and award-winning historian John Boessenecker separates fact from fiction in the first biography of the infamous crook in decades with his new book, "Gentleman Bandit: The True Story of Black Bart, The Old West's Most Infamous Stagecoach Robber," published by Hanover Square Press, an imprint of HarperCollins.

Mr. Boles, a voracious reader, took on the alias "Black Bart" in his thieving exploits from the story, "The Case of Summerfield" by American author William Henry Rhodes under a pseudonym in the early 1870s and first serialized in 1871 in the Sacramento Union and then widely reprinted by other newspapers. "Black Bart" was one of the villains in the story.

As he recounts the life and exploits of "Black Bart," Mr. Boessenecker also details the lawmen Mr. Boles eluded but who were constantly on his tail. He also tells of the family that Mr. Boles abandoned in favor of a life in crime.

"It's interesting that he encompassed the best and worst of a pioneer," Mr. Boessenecker said in a phone interview from his home near San Francisco.

Mr. Boles was born in England, the youngest of seven children born to John and Maria Boles. Mr. Boessenecker explains that Charles's grandfather was the "base child" of Elizabeth Birch and a man with the last name of Bowles, which account for different spellings of the thief's name through the ages. In the Times' clipping archive, a 1946 article, containing incorrect information according to Mr. Boessenecker, is filed under "Bowles, Prof. Charles E." Mr. Boles was never a professor and the only type of educator he became was when copycats tried to match his robbery exploits.

In a sea voyage filled with sickness, Charles's family arrived in New York City on July 1, 1830.

"The Erie canal was then only five years old, and it provided the best route west," Mr. Boessenecker writes in his book. "John (Charles's father) and Leonard Boles made their way to Jefferson County. The brothers each managed to acquire a 100-acre farm, where they began raising crops and dairy cows. John Bole's farmstead was located just south of Godfreys Corner, midway between the village of Plessis and the larger town of Alexandria Bay on the St. Lawrence River."

Mr. Boessenecker said that Charles Boles detested farming, and when word reached Plessis in 1848 of gold in California, the young man, then 19, wanted part of the rush. Instead of ship or wagon train, Charles hopped on a horse. "In the spring of 1849, as soon as the winter snow melted, he and his 19-year-old cousin David Boles started west, mounted on old farm plugs," Mr. Boessenecker writes.

Mr. Boles didn't find his fortunes in that gold-seeking trip or on others he went on as he roamed between east and west. In 1856, he married Mary Elizabeth Johnson in Iowa. Mary had also came west from New York State. A year later, they returned to the farm of Charles's father at Godfreys Corner, Jefferson County.

"Mary had a dowry, for Charley soon borrowed $400 from her, which was probably every cent she owned," Mr. Boessenecker writes in the book. "In the spring of 1860, he returned to Iowa, where he signed a deed transferring ownership of his farmland to Mary in exchange for the $400. Though Boles apparently deeded the farm to her as security for the $400 she loaned him, he had originally acquired the property for less than a quarter of that sum. What Charley did with the money is unknown, but Mary's decision to trust her husband would turn out to be the biggest mistake of her life."

The author explains that in 1860, Charles returned to Godfrey's Corner and moved his wife and two children to Decatur, Illinois. In August 1862, Charles enlisted as a private in Company B of the 116th Illinois Volunteer Infantry Regiment, assigned to the Army of the Tennessee, commanded by William Tecumseh Sherman. Engagements ranged from the siege of Vicksburg to the Battle of Atlanta. Charles was a brave, "quiet and gentlemanly" soldier and seemed to thrive on long marches. "His intelligence and schooling distinguished him from his fellow riflemen," Mr. Boessenecker writes.

"Those three chapters of the Civil War were probably the most difficult chapters I've ever written for a book because it was outside my wheelhouse," Mr. Boessenecker said. "Then it occurred to me that this stuff really explains the type of pillaging and foraging they did on the March to the Sea, surviving on miniscule rations and the whole idea that 'We can march through the south and take anything we want.' That sort of entitlement clearly influenced his later career."

Mr. Boles's Army service, the author writes, was the highlight of his life up to that point. But he sought something more: the financial success that kept eluding him.

Mr. Boessenecker shares the story of one of Mr. Boles's friends, who theorized on the moment that Mr. Boles decided to be a thief.

He was traveling about one day and sought food at a stranger's house. The food offered was an embarrassment to him. Charles, his friend's tale goes, and after rejecting the scraps and feeding them to the family dogs on the porch, told the man who offered him the meal, "Hereafter, when I want anything, I will take it."

"It just seemed that he felt he had this entitlement," Mr. Boessenecker said. "He didn't strike it rich in the gold rush, he then served his country and when it came time to be promoted to lieutenant, he got the promotion on paper but not the actual promotion because they didn't need another. Nothing seemed to go his way and I go into some of the events that his friends later said that led him to a career of banditry."

STRUGGLING BACK HOME

In the 1870s, while her husband was away on one of his mining unsuccessful escapades, Mary moved her family to Hannibal, Missouri, the home of her brother and his wife. "There Mary lived on the brink of poverty, eking out a living as a seamstress," Mr. Boessenecker writes.

Charles's parents, John and Maria, remained in Plessis. They both died in 1872 and are buried in the hamlet's Brookside Cemetery, with their grave stones noting the "Bowles" spelling of their surnames. Charles's uncle, Leonard, also died in 1872 after a fire struck the Plessis farmhouse of his son, Robert, where he lived, Mr. Boessenecker explains in his book. The fire also claimed the life of Robert.

Beginning in July 1875, Charles Boles robbed a total of 29 stagecoaches. He disguised his face with a flour sack.

Mr. Boessenecker, an award-winning historian on matters of the Old West and whose other books include, "Shotguns and Stagecoaches: The Brave Men Who Rode for Wells Fargo in the Wild West," said that robbing stage coaches wasn't like what is seen in Western movies.

"It's not like John Wayne with his Winchester '92, which had not been invented yet, on top of a stagecoach and the robbers are the Apaches or whatever chasing him," he said. "If they really wanted to stop the stage, they'd just shoot the horses."

But it was rare to be a lone bandit in a stage robbery, which was the modus operandi for Mr. Boles. In most cases, the horses of the bandits would be hid, the author explained.

"People back then knew horse flesh and often they'd give a better description of a horse than they would of the rider," Mr. Boessenecker said. "So the robbers would hide in the brush and rob the coach while it was going very slowly on an uphill."

But Mr. Boles would only rob stages while on foot, and not, Mr. Boessenecker writes in the chapter, "Myth and Mystery," because he was afraid of horses. "He walked to and from his holdups because that made it easier for him to avoid detection," the author writes.

Mr. Boles's first stage robbery occurred on July 26, 1875, on "the gradual slope of Funk Hill" in the foothills of the Sierra Nevada Mountains. Shortly after, readers are introduced to James B. Hume, Wells Fargo's chief and only detective.

The Delaware County, New York, native first went west to seek gold. But he would end up tracking Mr. Boles and Mr. Boessenecker writes an adventurous narrative of how Detective Hume and those he hired spent years tracking Mr. Boles and how he was eventually captured.

Mr. Boles would rob stages and return to San Francisco, finely dressed. The author writes that Charles did not drink, fight or consort with prostitutes.

He explained his routine absences by telling associates that he was involved in a mining company out of town that often needed his attention. In reality, when he needed more money to keep up his charade, he left town to rob more stages.

After Mr. Boles was caught in 1883, he spent his sentence at San Quentin Prison. He was 48 when he arrived to serve his six-year sentence, but due to good behavior, was released early on New Year's Day, 1888.

In the chapter, "A War of Words," Mr. Boessenecker shares a letter written to Charles while he was in prison from brother Hiram Boles, back in Jefferson County, asking "if he was his long-dead older brother." Charles responded that indeed he was, but "lost and in disgrace."

Mr. Boles would then write to his wife and daughters back in Hannibal, Missouri, saying that he would never return to a life of crime.

"He was full of it," Mr. Boessenecker said. "He'd become a real con man at that point. It's horrible to see the letters, "I love you,' 'I'm coming back to you,' 'I miss you.' It was all a big lie. Maybe he meant it at the time, but then, why didn't he send money back when they were struggling in Hannibal?"

Upon his release in January 1888, Mr. Boles would go back to robbing at least three more stages. He was never caught, and would disappear from everyone's radar.

The final fate of Black Bart isn't known but Mr. Boessenecker shared a "best guess." It involves a letter a Civil War comrade received from Charles, who apparently wrote that he was living in either Arizona or New Mexico as a successful rancher.

"Then again, it could have been Charley with his bologna, bragging because you couldn't believe anything he said," Mr. Boessenecker said.

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The DETAILS

WHAT: "Gentleman Bandit: The True Story of Black Bart, The Old West's Most Infamous Stagecoach Robber."

PUBLISHED BY: Hanover Square Press, an imprint of HarperCollins. 376 pages. Highly illustrated.

PUBLISHER'S DESCRIPTION: John Boessenecker sheds new light on Black Bart's beginnings, reputation and exploits, bringing to life the glittering story of the mysterious stage robber who doubled as a rich, genteel socialite in the golden era of the Wild West.

A REVIEWER'S VIEW: "Scrupulously researched and smoothly written, this is an entertaining slice of Americana." — Publishers Weekly.

LISTEN TO A SAMPLE: wdt.me/blackbartsample

COST: $33