In the colorful annals of the American West, tales of outlaws and bandits abound. Yet, finding a true ‘Robin Hood’ — someone who genuinely robbed from the rich to benefit the poor — proves to be a rare quest. While many figures were romanticized for their actions, few truly lived up to the legendary standard set in Sherwood Forest. However, an unexpected hero emerged from the banking world, challenging the conventional image of a Western outlaw.
The Outlaws Who Fell Short
Considered by many to be a folk hero, Jesse James gained sympathy in Missouri for his unwavering support of the Confederate cause, even after the Civil War. His targets were often banks and railroads, symbols of Yankee industrialization, and he reportedly avoided stealing from Confederate sympathizers. Despite this, his ill-gotten gains primarily served himself, his gang, and his family, rather than the wider impoverished community.
Charles Bolton, famously known as Black Bart, was a master stagecoach robber in California. He was known for his polite demeanor, especially towards women, and exclusively targeted the U.S. Mail and Wells Fargo express boxes, leaving passengers untouched. However, his proceeds were used to fund his lavish double life as a San Francisco gentleman, leaving his struggling family behind.
Butch Cassidy, another notorious figure, came closer to the Robin Hood ideal than James or Bart. He, too, targeted banks and railroads and displayed moments of generosity. For instance, his Wild Bunch once shot up Jack Ryan’s Bull Dog Saloon in Baggs, Wyoming, then paid the owner a silver dollar for each of the 25 bullet holes. While this won him local popularity, it wasn’t quite a systematic redistribution of wealth from the rich to the poor.
Charles Waggoner: An Unlikely Hero Emerges
A genuine Robin Hood figure did eventually appear, not as a gun-slinging cowboy, but in the unlikely guise of Charles Delos Waggoner, a respected banker in Telluride, Colorado. This was ironically the same town where Butch Cassidy committed his first bank robbery in 1889. Waggoner’s weapon of choice was not a Colt .45, but an expert understanding of banking laws and an unwavering determination to exploit them for the benefit of his depositors.
Waggoner arrived in Telluride in 1896, starting as a bookkeeper at the Bank of Telluride. His dedication saw him rise through the ranks, becoming cashier in 1907 and eventually bank president in 1919. By the late summer of 1929, Waggoner realized his bank was on the brink of collapse, and he resolved to protect his depositors, no matter the personal cost.
The Great Waggoner Swindle
Waggoner meticulously planned his audacious scheme. On August 30, 1929, he sent encoded telegrams, using a confidential bankers’ code, to six prominent New York banks: National City Bank, First National Bank, Harriman National Bank and Trust Company, Chemical Bank and Trust Company, Equitable Trust Company, and Guaranty Trust Company. These telegrams, falsely originating from their Denver correspondents, instructed the New York banks to transfer a total of $500,000 to the Bank of Telluride’s account at Chase National Bank.
The very next day, Waggoner personally appeared in New York to draw certified checks on these newly acquired funds. He then used this substantial sum – equivalent to approximately $8.5 million in 2022 – to settle the Bank of Telluride’s outstanding obligations. This masterful maneuver effectively shielded his depositors from losing their life savings in the bank’s impending failure. The use of certified checks made it exceptionally difficult, if not impossible, for the affected banks to recover the money.
Discovery, Arrest, and a Conviction
The fraud remained undetected until the New York banks confirmed the execution of the orders with their supposed Denver correspondents, who, of course, denied any knowledge of the transactions. In September 1929, Waggoner was arrested at a tourist resort near Newcastle, Wyoming, having made no serious attempt to evade capture. He was arraigned in New York on six federal counts of using the mail to defraud, with an unattainable bail of $100,000, ensuring he remained in custody.
En route to New York for trial, Waggoner made a stop in Chicago, Illinois. There, he famously told the New York Times, “I think I am going to jail for the rest of my life, but I can honestly say that I am not the least bit worried. My mind is at ease because I know that I have saved thousands of working people who trusted me and had deposited every penny they could save in my bank. Eighty percent of them were paid off before this happened. What they do to me now doesn’t matter much except, of course, that it is going to make my wife, my son, and my friends feel bad for me.”
Despite some minor courtroom theatrics – including Waggoner granting a newspaper interview while still in custody and witnesses complaining about meager allowances – he admitted sending the telegrams and accepted sole responsibility. He was sentenced to 10 years in the Atlanta Penitentiary, with both Judge Coleman and U.S. Attorney Tuttle recommending he serve at least five years. He began his sentence in November 1929, as the nation reeled from the stock market crash.
A Life After Prison and Lasting Legacy
Waggoner’s crime, apprehension, and trial unfolded against the tumultuous backdrop of the 1929 stock market crash, which plunged the United States into the Great Depression of the 1930s. His actions highlighted the immense financial instability and public fear surrounding banks during that era, making his sacrifice for depositors even more poignant.
Paroled in May 1935, Waggoner faced the challenges of finding employment as a convicted felon during the Depression. He sought help from an old friend, J. Walter Eames, who ran the Biltmore Club in Grand Junction, Colorado, reportedly owing Waggoner a past favor. Waggoner worked there, either in the office or at a gaming table, until unwelcome publicity arose in 1938 when Eames was tragically killed during a robbery attempt at the club. In 1939, Waggoner moved to Reno, Nevada, where he found work selling brushes. He passed away in 1960 at the age of 87.
Charles D. Waggoner truly embodies the spirit of a Robin Hood. He literally ‘robbed’ from the wealthy New York banks, not for personal gain, but to protect the savings of the less fortunate – the farmers, ranchers, miners, and local business people who were his bank’s depositors. He paid for his altruistic efforts with several years in prison. Whether one views Waggoner as a
