Could a gift of shares qualify as a gift by will where the will directs that shares with an unrealized capital gain shall be donated to a registered charity in such numbers as to eliminate the taxes of the deceased, or to only eliminate the deceased's taxes on the capital gain on those shares? After noting that “the will must require the executor … to distribute the bequeathed property to the designated legatee,” CRA stated:
[A] gift the amount of which is left to the discretion of the executor or the deceased's legal representative is not a gift made by will. In addition, where the amount of the gift cannot be determined, no donation deduction will be allowed in respect of the gift.