Despite a promising career in the New York State Assembly, Theodore Roosevelt left Albany and sought refuge on the banks of the Little Missouri in Dakota after suffering a personal tragedy and political disappointment. He announced his engagement to Alice Hathaway Lee on February 14, 1880, and voted against labor union-supported bills to increase the pay of policemen and firefighters in New York City in March 1882. Theodore's first child, a girl, was born on February 13, 1884 while the legislature was hours away from approving his bill that would strip the New York City aldermen of their power to confirm the mayor's appointments. The measure was his most promising bid to promote good government in New York. The following day, his mother, Martha Bulloch Roosevelt, and wife died. This chapter examines Roosevelt's conception of public virtue as private morality, his understanding of urban politics, and his view of race. It also looks at Roosevelt's romantic warrior mentality and how he folded it into neo-Lamarckian evolutionary theory to create a personal code of conduct.