Sounds like he is trying to cover something up or hide something.
This is not something pilots need to be doing. It impacts the rest of us that are following the rules.
Bottom line is if he gets in an accident where he failed to mention something on his medical application that he thought would be kept a secret behind Medicare, guess what....Insurance won't pay a dime, he will lose his license, get a big fine, maybe even charged with fraud and the rest of us will have more rules to follow...
If he has something that he thinks might impact his medical, he needs to talk to one of the EAA's or AOPA's medical advisors to see if it will or won't (no risk associated with this) and if it will, go thru the special issuance process like many of us have to be legal.