 In October 1996, while serving as President of the Puerto Rican Bar Association, Ocasio published a letter in the Chicago Tribune criticizing journalist Georgie Anne Geyer for anti-immigrant and anti-Hispanic rhetoric.In 2006, Ocasio entered the race for Judge of the 6th Judicial Subcircuit.Although he was rated qualified to highly qualified by all 10 bar associations in Cook County, the Democratic Committeeman chose to slate Ed Lechowicz, son of former State Senator and Cook County Commissioner, Ted Lechowicz.