change of directors interest notice, page-24

Regarding the "crazy not to" the obvious point is that he could've sold the heads to pay for the options without having to put new money into the company (other directors may still have done this).

Half the thread is discussing what didn't happen (failed to convert) or what might happen in the future (sell the new shares) rather than what did happen, he put a quarter of a million dollars in this market into the company.