How do you know?
This happened in New Jersey, right? In NJ health insurance companies could only not cover preexisting conditions for up to 12 months. The man could have bit the bullet and bought health insurance years ago.
Yes, you're absolutely right that if he literally waited until the very last minute to get health insurance to cover his health problems then in most states it probably would have been too late.
I guess this is the way things are going to be in the future; fuck paying for health insurance, just wait until you need it then pay 20 bucks for it. What could possibly go wrong with this plan?