Sometimes executive bonus programs include funds for them to buy underwater options. This can be in the form a of a loan or as a grant for the explicite purpose of stock purchase. It is done as form of comp or bonus but is rare. So what you say? Well if he wants to own stock for some reason (say he expects it to go a lot higher) then this is his chance to get in at a lower level...poof. The obvious other option is to to let it go higher then exercise options as it goes by. Anyways, it is not a bad thing as a stock holder I say, go for it.