The fact is that
1. Jolovan Wham did organise a physical gathering of people 2. The gathering/assembly meets the definition as in the Public Order Act[1] 3. The venue, The Agora, meets the definition of a public place as in the Public Order Act
[1]: https://sso.agc.gov.sg/Act/POA2009
They could have been watching a recorded video and it would have been the same.
> The Singapore Police Force in an earlier statement, said that Wham had organised an indoor public assembly featuring a foreign speaker, which required a Police permit.
Although given that political films are also banned, maybe a prerecorded video would have been illegal under a different law.
This is basically the difference between East Asian cultures and Western/American culture. We value a balance of order and individual rights, you guys value individual rights over all.
I know this is controversial, because the current rule is that you are not supposed to say that your moral system is right and the other guys system is wrong, but A is A and Freedom is not slavery, no matter how much that is yelled from the tops of mountains.