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Theodore Roosevelt is bound for greatness—he's a Harvard graduate from a prominent family, a rising politician, and his wife, Alice, is pregnant. Then his promising future turns tragic. His mother succumbs to typhoid, and Alice dies in childbirth on the same day. Devastated, Teddy leaves his urban world of high rises and high society for the desolate Dakota Territory, where, by facing the harsh reality of surviving life on America's frontier, he intends to remake himself into something greater.
When a masked bandit terrorizes the stagecoach line, killing a passenger, Theodore Roosevelt and his Elkhorn men join the citizens of Medora to track down the culprit. All the clues point to Redhead Finnegan, a petty criminal and ne'er-do-well who is suddenly flush with cash. The townsfolk confine Finnegan in an abandoned cavalry jailhouse, but he soon escapes and the stagecoach robberies resume. Deadwood's sheriff arrives to help lay a trap, but things aren't at all what they seem. In the end, it's the town's newspaper publisher who finally puts the clues together and identifies the killer, bringing his reign of terror to an end.
When raging wildfires threaten to consume Elkhorn Ranch, Theodore Roosevelt's men take quick action to avoid catastrophe, but many cattle perish in the flames. Backed into a financial corner, Roosevelt decides to sell some of his remaining stock to the town's founder, the Marquis de Morés, before the fall roundup. When the Marquis attempts to take advantage of the situation by making a low offer on Roosevelt's herd, a prideful Roosevelt walks away from the deal. Soon, other ranchers follow Roosevelt's lead, and the Marquis retaliates by closing his businesses in town, igniting violence between the area's ranchers and businessmen. To restore order, the town decides to form a cattlemen's association. With the ranchers poised to vote for the association's leader, Roosevelt must decide if he's truly finished with politics.
Theodore Roosevelt and his Elkhorn men strike out for the open range to participate in their first roundup. The weeks-long undertaking of sorting cattle is a chance for Roosevelt to prove himself a true cowboy. Unfortunately, the changing seasons bring back his asthma, and he is injured in a fall. Undeterred, Roosevelt rides alongside the rest of the cowboys as they drive and sort their herd across the Badlands. But the spirit of adventure quickly turns to fear when one of the cowboys turns up dead. Though it looks like an accident, some of the men aren't so sure, and the sudden appearance of the Marquis de Morés puts Roosevelt's mind ill at ease. With the cattle season coming to a close, Dow ponders if he should return to Maine as planned or stay in Medora to build a future with Rosie.
When a lightning strike spooks the herd, an injured Theodore Roosevelt acts quickly to stop a stampede during the fall roundup. Back in town, the annual roundup dance brings the community together, friend and foe alike. What should be a joyful celebration turns ugly when Paddock decides it's time to settle old scores with the Elkhorn crew. The dance is also Wilmot's best chance to propose marriage to Rosie, but her heart is torn between a simple life as Wilmot's wife and a more alluring future as Medora's protégée. With the Elkhorn ranch secured for the winter under the watchful eye of Merrifield, Roosevelt returns to New York to be reunited with his daughter.
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