He fell madly in love with, and they married on October 27, 1880. After moving to New York, Teddy decided to go into the field of politics. With the help of Jack Hess and Joe Murray, Roosevelt was elected to his first political office in 1881 as a representative for the New York Assembly. At the age of 23, he was the youngest man on the floor. He would not be bound by the political machine and would fight for what he believed in. He was soon appointed as a member of the Committee of the City. .
Soon afterwards, his reputation as a reformer began to build. He introduced four reform bills immediately after entering office. Because of his strong personality Roosevelt was elected for two more terms. He introduced a bill that became known as the Roosevelt Bill which wanted to pass more power to the elected officials such as the mayor. Then on February 12 his first child, Alice was born. But with the happiness, tragedy was not far behind. On February 14, Roosevelt lost his mother to typhoid, and within hours, his wife died of Bright's disease. This completely destroyed Roosevelt. He never spoke of Alice again, and decided to move to the Badlands of North Dakota. He left the care of his newborn Alice, under the supervision of Theodore's sister Bamie. .
In North Dakota, Theodore would rebuild himself from his losses, and sort out his emotions. Because he was able to carry his own weight, Roosevelt won the respect of many cowboys, that would help him in his future career. He started two cattle ranches, and became a man of the West. But because he was losing money in the cattle business, Roosevelt returned back East in October of 1886. When he returned to New York, Roosevelt was offered, the Republican nomination for Mayor of New York. He accepted although he knew that there was not much chance in him winning. But through his speeches, he was able to receive much attention. Yet despite all his work, he did not win.