> He probably married within his social circle of the Singapore intellectual elite whose members certainly have a much higher chance to reach such a position than the average joe in the country.

Probably irrelevant, but I wanted to add that Ho Ching is his second wife. The first Mrs Lee died three weeks after giving birth to his first son [1].

[1] https://wiki.sg/index.php?title=Death_of_Wong_Ming_Yang_(198...