While he was in Anglo-Chinese School, 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.
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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.
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Choo was given the name "Winston" by his grandfather, who named him after Winston Churchill.
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