Winston Choo Winston Choo Wee Leong ( born 18 July 1941 ) is a retired Singaporean military officer . He was the first Chief of Defence Force of the Singapore Armed Forces from 1974 to 1992 , holding the rank of Lieutenant - General . Early life and education . Choo was given the English name " Winston " by his grandfather , who named him after Winston Churchill . He grew up in Makepeace Road ( in the Newton area ) and received his education in Monk ' s Hill School ( 1947 – 1952 ) and Anglo - Chinese School ( ACS ) ( 1953 – 1957 ) . While he was in ACS , he captained the school ' s football team , played hockey , and won the Queen ' s Badge ( now the Founder ' s Badge ) for his activities in the Boys ' Brigade . Military career . Choo enlisted in the Singapore Military Forces ( later renamed to Singapore Armed Forces ( SAF ) in 1961 ) in December 1959 and was commissioned as a Second Lieutenant in December 1961 after completing his officer cadet training in Port Dickson , Malaysia . Following that , he served as a platoon commander in the 1st Battalion Singapore Infantry Regiment ( 1 SIR ) and was involved in two major operations : being deployed to Sebatik Island , Borneo between 1963 and 1964 during the Konfrontasi ; patrolling the streets during the 1964 race riots in Singapore . When Singapore became independent on 9 August 1965 , Choo , who was then the battalion signals officer , was appointed the first military aide - de - camp to Singapore ' s first President , Yusof bin Ishak . He was recalled to the SAF in 1966 and served as the first Commanding Officer ( CO ) of the 1st Signal Battalion from 1967 to 1968 . Between 1968 and 1969 , Choo attended the Long Telecommunications Course at the School of Signals in the U . K . , returning to Singapore to serve as the Second - in - Command ( 2IC ) of the 1st Signal Battalion . In 1970 , he was appointed as the Chief of Communications and Electronics ( now the Chief of Signals ) . In 1971 , Choo served briefly as the CO of the 4th Battalion Singapore Infantry Regiment ( 4 SIR ) before attending the Command and General Staff College at Fort Canning . In the following year , he attended the US Army Command and General Staff course at Fort Leavenworth in Kansas , U . S . , and graduated with distinctions in all his subjects . Upon his return to Singapore in September 1972 , Choo assumed command of 1 SIR . In the same year , he was named an honorary aide - de - camp to Singapore ' s second President , Benjamin Sheares , and took up command of the 2nd Singapore Infantry Brigade ( 2 SIB ) . He was also promoted to the rank of Colonel . He was later posted to the Defence Ministry ( MINDEF ) ' s headquarters , where he was appointed the Head of Training and Head of Organisation and Plans in 1973 . In 1974 , he succeeded Kirpa Ram Vij as Director of General Staff ( renamed to " Chief of General Staff " in 1976 ) . Choo was promoted to Brigadier ( now replaced by Brigadier - General ) in 1976 and to Major - General two years later . Between 1978 and 1981 , Choo attended a preparatory course in military history at the Department of History of the National University of Singapore ( NUS ) . In 1982 , he went to the U . S . to study for a Master ' s Degree in military history at Duke University and returned to Singapore later that year to resume his post as Chief of General Staff . Choo was promoted to Lieutenant - General in 1988 and became the first Chief of Defence Force ( CDF ) in May 1990 after " Chief of General Staff " was renamed . He also completed an Advanced Management Program at Harvard University in 1992 . He retired from the SAF on 30 June 1992 . Diplomatic career . After retiring from military service , Choo pursued a career in the Ministry of Foreign Affairs ( MFA ) . He was Singapore ' s High Commissioner to Australia and Fiji from 1994 – 1997 and to South Africa from 2001 – 2005 . He was also a non - resident Ambassador to Papua New Guinea from 2000 – 2006 and to Israel since 2005 . Other work . Apart from his military and diplomatic careers , Choo also took on important roles in various organisations ( both government and non - government ) , including : deputy chairman of the Central Provident Fund ( 1992 – 1994 ) ; chairman of Chartered Industries ( 1992 – 1994 ) ; board member of Singapore Technologies ( 1984 – 1992 ) ; board member of Keppel - Tat Lee Bank ( 1992 – 2001 ) ; chairman of the board of Metro Holdings ( 2007 – present ) ; chairman of the Singapore Red Cross Society ( 1996 – 2008 ) ; member of the Singapore Sports Council ( late 1970s ) ; member of the National Youth Achievement Award Council ( current ) ; third honorary president of the Boys ' Brigade ( 2011 – present ) . Choo has contributed to several publications , including his recollections of Goh Keng Swee , and of his time in the Singapore diplomatic corps . He also supported the Dads for Life movement in Singapore by contributing to the book " Letters from Grandpa and Grandma " ( pub . 2008 ) . Personal life . Choo has two sisters . He is married to Katherine Seow Guat Lee since 1966 . They have two children and four grandchildren . Awards . Throughout his career , Choo obtained many medals , some of which were on display at a National Library Board exhibition in 2006 . What follows is a partial list of his medals :