From what I can tell, Medicare doesn't run out, and its benefits are not contingent on employment history.
It doesn't sound like he's hospitalized right now. (Medicare covers 90 days of hospitalization per benefit period, with a lifetime reserve of 60 days that does run out.)
The hospitalization part of Medicare has no cost -- all you have to do is be in the right age group and sign on the dotted line. The cost segment of Medicare deals with medical procedures other than a hospital visit.
As far as I understand it, the present campaign is described as being for his after-hospitalization expenses.
It doesn't sound like he's hospitalized right now. (Medicare covers 90 days of hospitalization per benefit period, with a lifetime reserve of 60 days that does run out.)