Anyone who knows Gary knows he’s a (relatively) gentle human being. I can’t imagine him hurting a fly.
His tweets seem totally out of character compared to the Gary Tan I personally knew. Maybe he has changed?
I’m inclined to give him the benefit of the doubt.
This is the kind of shitpost most people would be able to get away with, but Tan is now too important -- and will have to curate his communications more. Especially if he's going to take such a strong position against incumbent politicians cautious of their own images.
It also feels like a smart political play by his targets to discredit him. They were probably waiting for him to slip up and say something like this.
Anyways, his position is a sympathetic one - the city is not well managed. I say this as someone who frequently disagrees with Tan.
The fact it’s a Tupac lyric is not like common knowledge. I doubt a random poll of Twitter users would show most people would know the reference immediately.
I'm vaguely aware of him, and his name and how he died are fairly well known, but I couldn't name a single track if my life dependent on it.
But even with artists "everyone" listens to, most people's listening is limited enough that assuming people know their lyrics would be stupid.