John Dean Caton had been in Chicago for two weeks, and the $14 he brought with him was nearly gone. Caton left New York in June 1833, gambling on making a living as a lawyer in a most unfamiliar place. Three years earlier, Chicago — not even an official city yet — had a total of about 30 residents. The year Caton arrived, it finally reached the 150-person threshold required to incorporate as a city. The Army’s Fort Dearborn was the main attraction, located south of the Chicago River. The land …