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Otherwise someone like Eric Tan would have been in parliament as NCMP. Deserving though he was , it did not fit with ambitions of the party. Do not underestimate LTK.
Anyone who has met Eric Tan will know that once this guy opens his mouth, it is impossible to shut him up. At any dinner table of x people, he is the only one speaking and can go on for 3 hours.
That solves the mystery of why the party chose Gerald. Nothing to do with old or young, past or present.
Of course if you are the kind who like this types to take on the PAP, by all means.