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I don't think he can qualify for GI because he is coming off a group health plan which pays secondary to Medicare but it is not a Medigap plan.
If understand correctly, what you just described is guaranteed issue right situation 2.
https://www.medicare.gov/find-a-pla...staticpages/learn/rights-and-protections.aspx
The real issue is what you stated in your first post, the timing.
Have You considered Newby's suggestion above?