Kammala wannan magana: An haifi Osborne a Orange, New South Wales, kuma ya yi karatu a Makarantar Sakandaren Arewacin Sydney da kuma Sydney Church of England Grammar School. Ya kammala karatunsa a fannin shari'a daga Jami'ar Sydney. Ya shiga Royal Australian Naval Volunteer Reserve a 1938, kuma tare da barkewar Yaƙin Duniya na Biyu, an tura shi zuwa Royal Navy a 1940. An ba shi lambar yabo ta Musamman a shekarar 1940 don "jaruntaka da sadaukar da kai ga aiki" yayin taimaka wa...
kwashe dakarun daga Norway a matsayin mataimakin laftanan a kan "St Loman", wani jirgin ruwa mai dauke da makamai. Daga nan sai ya yi umurni, kuma, ya bi jirgi tsakanin Amurka da Kanada da Ingila a cikin Yaƙin Atlantic. Ya haye Atlantic sau 22 kuma shine kawai Royal Australian Naval Volunteer Reserve jami'in da ya tashi zuwa umurnin wani jirgin ruwa na Royal Navy a lokacin yakin. A cikin 1945 an ƙara Bar zuwa DSC don nutsewar jirgin ruwan Jamus.