During his junior year at Harvard, Teddy met and fell in love with Alice Hathaway Lee. The daughter of a prominent Bostonian and the cousin of one of Teddy's classmates, Alice quickly captured his heart. With golden curly hair, blue eyes, cute face, and charming wit, many young men fell for her, and it took Teddy a considerable amount of time and energy to win her heart. Rather than study, he spent many afternoons riding his horse or even walking the six miles from Harvard to her house on Chestnut Hill. They often took lengthy walks and carriage rides together, read poetry to each other, and played board games. At the end of his junior year, he proposed marriage, but she neglected to answer. Nevertheless, Teddy continued to pursue Alice; in fact, he spent so much time with her that his grades dropped considerably during his senior year. Finally, after eight months he proposed again. This time she gladly accepted. On October 27, 1880, Teddy's twenty-second birthday, the two were married. Deeply in love, the couple moved to New York City to live on the third floor of the Roosevelt family residence.
Unsure what career to pursue upon graduation and unwilling to take over the family business, Teddy decided to study law, a subject that had always intrigued him. He also continued working on his first book, A History of the Naval War of 1812, which he had begun while still at Harvard. He enrolled at Columbia Law School in 1880, but within two years became disillusioned with the drudgery of the work. Although he continued to live blissfully with Alice, he desired something more and, against the wishes of his family and friends, entered politics. During this period in New York City, local politics was a rough profession. Powerful politicians known as "bosses" ran political machines and controlled the majority of local elections, winning votes from New Yorkers via coercion, extortion, and the threat of violence. One of the most notorious of these machines was Tammany Hall. The conservative, young Roosevelt began frequenting the headquarters of the local Republican machine, Morton Hall. He made friends quickly and soon found himself running for a seat representing the twenty-first district in the New York State Assembly. He beat the opposing Tammany candidate easily. At this point Roosevelt was only twenty-three years old.
Roosevelt's first term as an assemblyman began in January 1882, and he immediately distinguished himself from the other representatives. With his Harvard upbringing, dress, confidence, and especially his young age, many of the older lawmakers quickly branded him a "dude." At the same time, however, he also demonstrated an unexpected earnestness and competency. Within just a few weeks of his first term, Roosevelt denounced New York Supreme Court Judge Theodore Westbrook as a co-conspirator in a recent railroad investment scandal that had destroyed the livelihood of many legitimate investors. The shocked assembly tried to sidestep Roosevelt's request for an investigation, but he outmaneuvered them and won the right to investigate. No charges were brought against the judge, but Roosevelt won fame as an unconventional politician willing to defy the powerful in the pursuit of justice. Later in the year, he also challenged the excessive power of the political machines and introduced a bill in the assembly that would alter the way local elections were conducted. For this reason, conservative Republicans shunned Roosevelt, but he received wide approval from the press and became famous throughout New York.
Within a year of entering public life Roosevelt had established a style of his own that he retained throughout his life. He was a reformer. He challenged convention to achieve what he believed to be morally right. He handled controversy well, a trait essential for someone with his thirst for quick action. His second year in the legislature brought even more success. Although the Democrats held a majority of the membership, the Republicans nominated Roosevelt for the assembly speakership, which instantly elevated him to the position of Republican minority leader within the assembly. He continued to seek reforms that would improve the lives of average New Yorkers. He sought legislation to establish a park in the city and to toughen penalties for men who abused women and children. He also continued to strive towards machine-election reform. He earned a reputation as a bipartisan cooperator when he worked with Democratic New York Governor Grover Cleveland to reform the spoils system within the state civil service commission.
Riding on his success, Roosevelt was elected to a third term. During this election year, the Republicans had done well at the polls and became the majority party in the New York State Assembly. Roosevelt expected to be named Speaker; however, his hopes were unexpectedly dashed by a coalition of conservative Republicans and lobbyists who united to select a more conservative Speaker.
By this time Alice was very pregnant and about to deliver their first child. On February 12, 1884, while Theodore was away at the assembly in Albany, Alice delivered a baby girl. A telegram was sent to Albany, and congratulatory cheers filled the assembly hall. Within hours, however, a second telegram arrived, this time instructing Roosevelt to return home immediately to tend to Alice, who had suddenly become very ill. Theodore rushed home and arrived in time to find Alice dying from kidney failure, an unforeseen complication of the pregnancy. She died the morning of February 14, 1884. Tragically, Theodore's mother had died just hours before, on the same day and in the same house. Theodore was with both of them during their last hours.