The age requirement at that period of time was 11. His younger brother certainly qualified for eventual NS exemption. Press reports state that he was 12 when he left, so he did not make the cut. All young male Singapore passports at that time expired when your DOB at age 11 even if applied for one a few month before 11 years of age.
The age was upgraded later to 13 and no longer tied to the renewal of Singapore passport.
The age was upgraded later to 13 and no longer tied to the renewal of Singapore passport.
I am basing the age he emigrated based on reports that he is 28 now and emigrated 18 years ago in Dec 2000. This means he would have emigrated when he was about 10/11. We won't know exactly as his month of birth has not been reported. It should be in Jun/July though as his first "Registration for NS" letter (sent by CMPB within 2 weeks after one reaches 16.5) was in Dec 2005. This would mean he emigrated when he was about 11.5 years (again assuming he was a Jun/Jul baby).
But that's not crucial. What is important is that he passed that magical age of 10 when he emigrated. It is an arbitrary age that the Singapore Government deems one to have "enjoyed substantial socio-economic benefits" which then requires these kids to serve NS. The age may have changed to 8 but I don't want to pull stories out of my ass to claim that this 8 is gospel truth without being able to source it or provide evidence. So, that age of 8 is strictly speculative.
I can't believe he thought he could get away. Either that or he was blissfully ignorant of the rules which is equally shocking considering his "status". If not, it would mean he is hopelessly lacking in foresight and failed to realise that come one day, his sons would in all likelihood, have to return to Singapore for one reason or another before their deaths.