[30] In 1866, he successfully defended some participants in the Fenian raid, working on a pro bono basis (free of charge).[31] In 1868, Cleveland attracted professional attention for his winning defense of a libel suit against the editor of Buffalo's Commercial Advertiser.[32] During this time, Cleveland assumed a lifestyle of simplicity, taking residence in a plain boarding house. He devoted his growing income instead to the support of his mother and younger sisters.[33] While his personal quarters were austere, Cleveland enjoyed an active social life and "the easy-going sociability of hotel-lobbies and saloons."[34] He shunned the circles of higher society of Buffalo in which his uncle-in-law's family traveled.[35]

Political career in New York
Sheriff of Erie County
Statue of Grover Cleveland outside City Hall in Buffalo, New York
From his earliest involvement in politics, Cleveland aligned with the Democratic Party.[36] He had a decided aversion to Republicans John Fremont and Abraham Lincoln, and the heads of the Rogers law firm were solid Democrats.[37] In 1865, he ran for District Attorney, losing narrowly to his friend and roommate, Lyman K. Bass, the Republican nominee.