Cooley was appointed as an appraiser of property and slaves for Union Bank of Florida. His ally, Richard Fitzpatrick, purchased his coontie and citrus plantation on the Miami River for $2,500. Subsequently, Fitzpatrick was elected as representative for Monroe County to the Territorial Legislative Council. The unanimous vote for Fitzpatrick in New River was questioned by the "Key West Inquirer". Cooley's conduct was implicitly questioned as well, since as Justice of the Peace, Cooley conducted the non-secret balloting. In Key West, Fitzpatrick lost to William Hackley.