It can definitely be legal as a gift. One problem is he gave them to a person to hand out as seen fit. Transfer does have to be documented. Unless of course he was taking the bearer shares route which is a whole different gamut than gift.I highly doubt this stock will be trading when the restriction on these gift (or other) shares end.
'Giving' shares, and your I R S. In Canada our tax rules are firm. If I 'give' shares to my family they carry my cost base for tax purposes. I don't get any tax liability. BBBBBUUUUUTTTTT .. if I 'give' YOU any shares, they take on the fair market value at the time I gave them to you. That becomes your cost base. It also gives me [Urban] tax liability. NOBODY beats the tax man. I wonder if Urban thinks that he can.