Theodore Roosevelt rides in an open carriage toward the U.S. Capitol for his March 4, 1905, inaugural. A troupe of cowboys from Teddy's beloved West were the hit of the parade. (Library of Congress)

‘Mounted on their spirited ponies, the cowboys were decked out in high style—wide-brimmed, high-domed sombreros, colorful neckerchiefs, chaps, heeled boots and prominently displayed six-shooters’

Under the long shadow of the assassination of President William McKinley, the September 14, 1901, inauguration of Theodore Roosevelt as the 26th president of the United States—held at a friend’s house in Buffalo, New York—was a somber ceremony without pomp. But following his reelection in 1904, officials laid plans for a gala event. Among those who wanted to honor Roosevelt in a spectacular manner was Seth Bullock, celebrated former sheriff of Deadwood, Dakota Territory. Bullock contacted Roosevelt and suggested bringing a contingent of cowboys from the Dakotas and neighboring states to Washington, D.C. Mounted on cow ponies and decked out in Western garb, they would join in the inaugural parade. Roosevelt’s response? “Bully!”

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Long before that, of course, Roosevelt had cultivated a cowboy image—never mind his 1858 birth into a well-to-do, aristocratic family highly placed in New York political and social circles. A voracious reader of powerful intellect, he earned a degree from Harvard University and seemed on his way to a successful career in politics, embracing all the attributes and inadequacies of Eastern snobbery that path presented. But young Roosevelt had a strong adventurous streak, despite suffering from asthma, poor eyesight and general physical weakness. Thus in 1883, 24-year-old Teddy, enthralled by tales of the frontier, decided to venture to Dakota Territory and sample some of that excitement himself. Over the next five years he frequented the Dakotas to ranch and hunt, and he came to know and admire Westerners, especially ranchers and cowboys. He ultimately returned East to resume his political career, but the Western experience had changed him forever. (See cover story, this issue.)

When war broke out with Spain in 1898, Roosevelt resigned as assistant secretary of the Navy to help form the 1st U.S. Volunteer Cavalry, a regiment he insisted be composed of Western fighting men. Offered command of the unit, he declined, instead accepting a commission as lieutenant colonel under the more experienced Colonel Leonard Wood. But after Roosevelt led the Westerners in several victorious engagements, including the celebrated charges up Kettle and San Juan hills, the regiment won popular acclaim as “Teddy’s Rough Riders” and was forever linked to him.

Roosevelt’s Rough Rider experience strengthened his many friendships with Western frontier characters, and he maintained contact with a number of them, including Bullock, a seminal figure in frontier Montana and the Dakotas. In Montana Territory in the early 1870s, Bullock served as a senator and then as sheriff of Lewis and Clark County. In 1872 he introduced legislation that paved the way for the creation of Yellowstone National Park. Bullock and business partner Sol Star arrived in Deadwood on August 1, 1876, the day before Wild Bill Hickok was shot playing cards. The partners operated a successful hardware, and Bullock became de facto sheriff of the camp. He was appointed the first official sheriff in April 1877 when the territorial government carved out Lawrence County. Over the next two decades, Bullock had a successful career in business investment (after the Deadwood hardware burned down in 1894, he and Star built a luxury hotel on the site) and ranching in the Dakotas. Roosevelt met Bullock during his own stint in the Dakotas in the 1880s and renewed their acquaintance when Bullock led a contingent of Dakota cowboys into the Rough Rider regiment and was rewarded with a captaincy (though he saw no actual fighting in the war).

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