John likely hasn't had health insurance since The Tonight Show fired him.

Just speaking as someone who's had to navigate the 'marketplace' in recent years and the prices he's throwing around for the surgery.

Let's start with the 30k. There's no insurance on earth that has a 30k out of pocket maximum, or even something close to that. Most out of pocket maximums for the year are like 6-10k. Meaning once you hit that, your copays are done.

Secondly, once he was fired he probably was given the option to get insurance through COBRA for a bit, but even that costs money - it's not free. Same with the marketplace. You have to sign up yourself every year during open enrollment and then pay your monthly bill.

Do you guys think John has been keeping up with health insurance when that $300-500~ a month could go to Coors?

And he's too young for Medicare. Maybe he's on medicaid because of low income status? But that would again have taken effort to sign up for. None of these things magically happen.