In 1883, Theodore had traveled to the Badlands of Montana to hunt bighorn buffalo, and found his experiences there exhilarating. In the great outdoors, Roosevelt pushed himself to the extreme and had the most fun doing it. His experiences in the West significantly shaped many of his attitudes on life, hard work, and manliness. Within two days of roughing it out, he decided to become a cattle rancher. When his wife Alice Lee Roosevelt died and his third term in the New York State Assembly ended, he returned West to escape tragic memories and begin a new life as a cattle rancher. He spent nearly $40,000 on cattle and on his new home, Elkhorn Ranch, which was situated on the Little Missouri River in Dakota Territory, twelve miles away from the nearest house.

With the exception of a few trips to New York to visit his sister and baby Alice and to help several of his former New York Assemblymen in their political campaigns, Roosevelt spent most of the time between 1884 and the beginning of 1887 at Elkhorn. He lived quietly and arduously. During the day he tended the cattle, sometimes spending sixteen hours a day in the saddle; at night he worked on his literary career. By this time his A History of the Naval War of 1812 had been published, and it had instantly received high praise. Many considered it the finest work on the subject even decades after its completion; Roosevelt, however, thought the writing style too dull and dry. He also worked on other writings while in the Dakotas, publishing several articles for Eastern magazines about the rugged and glamorous life in the West. In 1885, he published an entire book on the subject, entitled Hunting Trips of a Ranchman, an essentially autobiographical work of his experiences in the Dakotas and Badlands of Montana. The style of this writing was much different from his Naval History, and he was able to write several chapters in as many days. In the next several years he published a couple of biographies of two New York politicians as well. He also began writing more serious pieces, such as a A History of the City of New York and his multi-volume work The Winning of the West.

Yet, as usual, Roosevelt's life was not without adventure and excitement. Besides tending the cattle and participating in the roundups he found so exciting, Theodore also spent many hours hunting buffalo, antelope, and grizzly bears. Although a city boy at heart, he loved playing cowboy, and his spectacles contrasted sharply with his sombrero, fringed buckskin shirt and trousers, spurs, and six-shooter. During his stay in 1883, he nearly became involved in a duel over a territory dispute with the Marquis de Mores, a Frenchmen who had come to Montana in search of adventure. Roosevelt also earned a reputation as a fighter. After a gun-wielding cowboy called him a "four eyes", Roosevelt punched him three times in quick succession, knocking the man unconscious. Along with his ranch hands, he also captured a band of three outlaws in 1886 when they stole his boat.

Theodore did not remain on the frontier for long, however. While visiting his sister and baby Alice on Christmas, he was reintroduced to an old friend, Edith Carrow. During his childhood years, Theodore and Edith had been sweethearts of sorts. While away in Europe for the first time, Teddy had written Edith all about his adventures. As a young girl and teenager, Edith had always assumed the two would someday eventually marry. For some unknown reason, however, the two stopped talking suddenly, soon after Teddy left for college but before he met Alice Lee. Edith later claimed that Teddy had proposed to her and that she declined at the time, saying she was not yet ready. In a letter to his sister, Theodore simply writes that he and Edith had a disagreement, but neglects to mention why. Edith congratulated Teddy at the announcement of his engagement to Alice, but truly felt crushed. When the two met again in 1885, Edith's hopes of marrying Teddy were renewed. Roosevelt, however, was more reluctant to marry again. He had always regarded marriage as sacred and had believed that marrying twice for any reason either showed a flaw in character or, in the case of the death of a spouse, unfaithfulness. It had also been less than two years since Alice had died, and Theodore felt extremely guilty for having even thought of loving Edith. But, after months of deep thinking and with the encouragement of his friends and remaining family, Theodore proposed to Edith in 1886. The two married in December of the same year.

When the couple returned from an extended honeymoon in Europe, they settled down to start a family in Roosevelt's recently completed twenty-three room mansion on Sagamore Hill in Oyster Bay, New York. In 1887 Theodore's first son was born. Roosevelt of course, named him Theodore Roosevelt III. Including baby Alice, who came to live with them after her third birthday, Theodore and Edith would eventually have six children: Alice, Theodore III or "Ted", Kermit, Ethel, Archibald, and Quentin. Roosevelt loved playing with his children, especially the boys, whom he understood better than he could Ethel or Alice. As Alice grew older she became indignant and rebellious, never quite feeling herself a true member of the family. Even when the younger Alice asked, her father refused to speak of the elder Alice, and her journals revealed that she felt he loved her less than he loved his other children. Until the day she married, she also constantly battled with her stepmother, Edith, who, for her part, considered Alice to be her own child.

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