[2] Isola had an early political success in an election to the Gibraltar Legislative Council in 1956, when ten candidates contested seven seats.
The winners were Joshua Hassan, Abraham Serfaty, J. E. Alcantara, and Albert Risso, all of the Association for the Advancement of Civil Rights, one Commonwealth Party candidate, Joseph Triay, and two Independents, Isola and Solomon Seruya.
In 1963 and 1964, he went to the United Nations together with Chief Minister Sir Joshua Hassan to oppose Spain's attempt to obtain sovereignty over Gibraltar using decolonisation as an argument to achieve its ends.
In 1964 Isola defended free association with the UK, which had been unanimously endorsed by the whole legislature as the constitutional formula for decolonisation, which was expected to be achieved by no later than 1969.
[5] Isola's Triumphant Return to Gibraltar in 1963 when he and Joshua Hassan were cheered by crowds in John Mackintosh Square has been recorded in a commissioned painting by Ambrose Avellano.