The problem with asking for tax advice is that if you happen to get a very clear answer (Slam-Click's link above) but claim anyway then you go from a good bloke who's made a genuine mistake to someone who has intentionally defrauded the ATO.
The answer to the OP's question is very clear, NO, neither of the hypothetical pilots may claim the endorsement. If you wish to go down the road of claiming anyway then it would be a lot better if you never asked the question and were therefore genuinely mistaken about the rules.