> I'm surprised at the general tone of response here towards the subject of poker overall [...] regarded as living a degenerate lifestyle

Maybe the people who are negative have read to the end of the article where we are let into the not-so-hidden agenda of the parent: Teach the kids to hustle their way through college so they can become a market speculator.

Matt Levine is “known for his humorous, witty, deadpan writing style” - I’m pretty sure that’s a joke.

I think it was at least partially joke. The author writes a popular newsletter called "Money Stuff", which is about weird things in the finance world.