Is There Any Possible Way to Make this Work?

I think this guy is screwed, but he said one of his friends was able to make it work without a gap so I am second guessing myself (I have a suspicion he is mistaken, but at the rate they change things on healthcare.gov, maybe he is right?)

18 months ago he retired, his large-group employer coverage ended the last day of employment, not the last day of the last month of employment. So March 12. April 12th, whichever..

Takes COBRA. Good thing he did because he had two heart attacks during the last 18 months.

Now he has his notice that COBRA is running out October 12th. If we apply
Source of insurance-forums.net

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