We have many restrictive laws here but they are very selectively enforced. As long as you stay away from "hot" topics such as direct criticism of the ruling party and sensitive issues such as immigration, you are ok. But if you make too many waves, there are many ways in which such selective enforcement can come back to bite you.
On an individual level, you will get much more attention on things like your tax returns. Your Provident Fund usage can be limited in many ways(It is a opaque system and they don't need to give you any justifications)
If you own a company, it will also be subject to a much higher tax scrutiny. They can choke your company by limiting the number of foreign talent that you can hire( again an opaque process). They can reject your applications without any reasons and simply say better luck next year.
Even with all these pressures, Singapore is a great place to do business and just enjoy a generally high quality of life as long as you don't do anything foolhardy or get really unlucky with the cards that you get dealt.
On a side note, if the person in question above was involved in some tricky business, then I would not put it past this government to take drastic measures