Richard Fitzpatrick, by that time the owner of a successful plantation with coconut and lime trees, plantains, and sugarcane, pressed for the appointment of Cooley as Justice of the Peace in 1831, making Cooley responsible for adjudicating disputes of persons and property, punishment of minor offenders by fines and whippings, and oversight of the activities of wreckers. Serious offenders were jailed in Key West. By that time, Cooley owned a schooner and took trips not only to take prisoners but to trade coontie, sugarcane, and tropical fruit with Cape Florida, Indian Key, Key West and Havana.