[1] After the Cuban Revolution on 1 January 1959, he was confirmed as head of the new Revolutionary Air Force as well as Castro's personal pilot.
On 29 June 1959, Fidel Castro relieved him of his post, and he left immediately by boat for Florida with his second wife and 3 of his six children, and reportedly with Frank Sturgis, a fellow anti-communist.
[2] On 14 July 1959, Díaz was interviewed by the US Senate Internal Security subcommittee, where he gave out the first account of Fidel's planned move towards communism.
[2] On 21 October 1959 he carried out one of his most notorious acts, flying a twin-engined bomber (variously reported as a B-25 or B-26) over Havana while dropping anti-communist leaflets, along with his brother Marcos Diaz Lanz.
The unsuccessful gunfire from armed forces on the ground caused injuries and deaths, leading to unsubstantiated reports of bombs being dropped from the aircraft.