By Sarah M. Boye
Dakota Bob poses in Orlando around 1911 beside a sign proclaiming 93,000 miles traveled on foot.
Standing before Orlando photographer Thomas Pickett Robinson’s camera around 1911, Dakota Bob looked like he had stepped straight out of an old western story. His dark hair cascaded over his shoulders, a broad-brimmed hat in his hand. Medals and badges covered his shirt. A walking stick rested at his side, while an enormous snakeskin draped across a nearby chair. On the side of the image, a handwritten sign proudly proclaimed that he had traveled 93,000 miles on foot and was nearing an incredible 100,000. To Florida residents in the second decade of the twentieth century, he was already a familiar face.
Dakota Bob arrived during the height of America’s fascination with long-distance walking. In the late nineteenth and early twentieth centuries, so-called “pedestrians” became celebrities as newspapers eagerly followed men and women attempting astonishing cross-country journeys. Osborne tapped into that craze, adding his own frontier flair to stand out from the crowd. Each winter, newspapers announced his return to Central Florida almost as reliably as the arrival of northern tourists. Tampa newspapers eagerly reported his visits, while theaters in St. Augustine advertised him as an “original entertainer” certain to draw large crowds.
But who was Dakota Bob? The man himself proved just as colorful as the character.
Long before he became Dakota Bob, he was George A. Osborne, born in Buffalo, New York, on March 10, 1861. His father worked first as a telegraph operator and later as a newspaper editor, and the family spent time in Connecticut and Michigan before returning to Buffalo. By 1881, Osborne was following in his father’s footsteps as a newspaper reporter. However, the following year brought dramatic changes. George’s parents divorced. Just one week later, his mother remarried, taking George’s six-year-old brother Clarence with her and changing the boy’s surname to Wells. A few months later, George’s father also remarried a much younger woman.
George’s own marriage around that time was short lived. Working as an actor in Indiana, he married Nettie Malcolm, who worked as a “dining room girl,” on December 22, 1882. Just six days later, he filed for divorce. Newspapers reported his claim that his new bride was “too loose of character, even for a second-class actor.”
Then George Osborne disappears. For nearly fifteen years, the historical record falls strangely silent. When he reappeared in 1897, George Osborne had become “Dakota Bob.”
Where the man ended and the character began is difficult to say. According to Dakota Bob, he had spent thirteen years living among the Sioux and had been adopted into Sitting Bull’s family. He claimed to have worked as an Indian scout, served as a range guard for wealthy cattlemen, reported on the Sioux uprising of 1890-91 for the U.S. Army, and traveled with Buffalo Bill’s Wild West show for two seasons, where Buffalo Bill himself supposedly gave him the name “Dakota Bob.” He also said he had carried official government seals between President Theodore Roosevelt and Mexican President Porfirio Díaz, circled the globe twice, crossed the United States six times, and eventually walked more than 100,000 miles.
Whether every story was true almost misses the point. People weren’t just following a long-distance walker. They were following Dakota Bob. By the turn of the twentieth century, he had become a celebrity in his own right. Newspapers followed his travels from town to town as he collected signatures from mayors and other officials, posed for studio portraits, and entertained audiences with stories, paper-cutting demonstrations, and comic impersonations. Each photograph, newspaper clipping, and autograph became another piece of the character he carried from town to town.
His frontier persona would have been instantly recognizable to audiences. Buffalo Bill’s Wild West had turned the American West into one of the country’s most popular forms of entertainment, and Dakota Bob fit into that world of scouts, cowboys, and frontier adventure. Orlando had its own connection to Buffalo Bill’s Wild West. When the show came to Orlando in 1912, its aging bison Barney the Buffalo escaped after an evening performance, charged down Orange Avenue, and died before he could be returned to the train. The incident became one of Orlando’s most enduring tales from the days when the Wild West came to town.
Florida quickly became one of Dakota Bob’s favorite destinations. In January 1909, the Tampa Tribune noted that although Tampa lay well off his route to Mexico, Dakota Bob “could not resist” visiting a city he had heard so much about. A few weeks later, St. Augustine’s Plaza Theatre promoted him as the featured attraction for three nights, advertising not his walking, but his “marvelous feats of paper tearing, mind reading and comic impersonations.” People did not simply gather to watch Dakota Bob walk through town. They paid to see Dakota Bob perform.
A later portrait celebrates Dakota Bob’s claimed milestone of more than 100,000 miles traveled on foot.
The photographs preserved in the History Center’s collection capture Dakota Bob’s carefully crafted public image. From handwritten mileage signs to medals, walking sticks, and well-worn scrapbooks, every object in the images helps reinforce the larger-than-life story he built around himself.
Dakota Bob reviews one of the scrapbooks he carried throughout his travels.
Dakota Bob rarely inspired indifference. Some newspapers promoted his appearances and treated him as a welcome entertainer. Others poked fun at his elaborate persona or dismissed him as a “freak.” The Orlando Evening Star captured both reactions, joking that his annual return heralded the arrival of the snowbirds while calling him “one of the very few unpleasant features of an otherwise delightful tourist season.” Whether admired or mocked, Dakota Bob remained a figure readers recognized instantly.
George Osborne spent decades building the legend of Dakota Bob, blurring the line between fact and folklore until the character overshadowed the man himself. After an injury in 1912 ended his pedestrian career, Dakota Bob became a familiar fixture at the Tampa Tribune, sleeping in the press room, selling newspapers, and entertaining staff and their children with stories of the West. When he died in October 1916, the newspaper mourned him as an old friend. Yet the city of Tampa still didn’t know his real name. Behind the walking stick, medals, long hair, and frontier stories was George A. Osborne, a former Buffalo reporter and actor. He was buried in a potter’s field under the name Dakota Bob, the only identity Tampa knew.
More than a century later, photographs, newspaper accounts, and newly uncovered genealogical records remind us that where George Osborne ended and Dakota Bob began is still hard to pinpoint. In the end, his greatest performance wasn’t a stage act or a long-distance walk. It was Dakota Bob. His story is the story of a man who turned himself into a legend, and of a legend that nearly erased the man.