On one hand raised in a household where English and Malay were spoken, English educated Lee struggled as head of the People's Action Party to learn Chinese--a dialect Hokkien and Mandarin. For him, learning them as an adult, no matter how fluent he became, psychologically it challenged a man of strong ego like him that he never was complete master of his Han ancestors' languages.
On the other hand, in 2009, he openly admitted that he was wrong to impose mastery of English as a common language for the plain and simple truth the Chinese young had become alienated from their language. Before imposing English as a common language which eminently made good common sense since not all Singaporeans are of Chinese origin. To create a new nation and a national identity, the PAP had to consider the Malays and Tamil speaking Indians who also are Singaporeans.
Lee's apology shrouds even more the hidden history of early Singapore. One to break the hold of the Chinese left wing and cultural nationalists, he suppressed the use of dialects in favour of Mandarin as a second language for Chinese. By doing this, he broke with his allies in his own party and adopted the recommendations of the British colonial authorities faced with a growing militancy among the Chinese educated who had funded and supported the Chinese language Nanyang University which Lee as prime minister emasculated and turned it into another university following the paradigm of bilingualism.
Now Singapore is beset by a falling birthrate among its own, reliance on infusions of Chinese from Communist China is a major source of keeping the dominance of the Chinese in Singapore. From here to there, it is not surprising to hear Lee crow eloquent about bilingualism and embrace of Mandarin. It has to be a crushing blow to his ego that as his 10 decade of life looms large, he has to made a volte face on Mandarin and encouraging a better Chinese educated Singapore--a goal he forcefully fought against to attain and maintain PAP dominance of Singapore's power elite.