I te tau 1954 i whakawhiwhia a Oliva ki te tūranga tuarua i te ope taua o Cuba i muri i tana tohu mai i te Whare Wānanga o Cuba, "te Kura Cadet". Whai muri i te tohu tohu mai i te Whare Wananga o Artillery i te tau 1955 ka tohua ia hei kaiwhakaako mo te Artillery i te Kura Cadet tae noa ki te 1958. Mai i te 1958 ki te 1959 he akonga ia, i puta ano ia me te honore, me te kaiwhakaako i te US Army Caribbean School i te Canal Zone, Panama
He aha? I te mutunga o te tau 1959 i muri i te hurihanga o Castro i te General Batista, i "whakakorehia" te ope ope Cuban, engari i tohua a Oliva hei Kaitirotiro Matua i te INRA. I te Haratua 1960 ko ia tetahi o te roopu o nga rangatira o mua o Cuba e whakamahere ana i tetahi pakanga ki te kawanatanga o Castro. He paetahi katoa rātau i te whare wānanga hōia o Cuba. I mahue ia i te ope taua i te tīmatanga o Akuhata 1960 ka rere ki Miami. I te Akuhata 29, 1960, ko Oliva me te 40 nga taiohi o Cuba i whakaraua, i whakauruhia e te Central Intelligence Agency, i kawea e CIA C-54 rererangi ki San José, Guatemala ki te whakahaere i te whakangungu guerilla i muri mai ka waiho hei tikanga.