Sears v. Coolidge 329 Mass. 340, 108 N.E.2d 563 (1952) Coolidge made an irrevocable inter vivos trust that gave one-thirds of its income to the children of his deceased sons, and split the other two thirds of its income into four parts giving one each to Marian, Sargent, and Sarah (presumably his living children), or their children after they died, and one to the children of the deceased Elenora. The trust would terminate and trust assets distributed in equal shares to all of Coolidge's descendents at either: The death of Coolidge's last child, grandchild, and great-grandchild who was alive at the time of his death, or The youngest of Coolidge's grandchildren living at the time of his death turned 50. The first termination clause might have violated the Rule Against Perpetuities. Since it was an inter vivos trust, it was executed immediately. It was theoretically possible for Coolidge to have had another grandchild after the trust was executed. If that grandchild has survived everybody else by more than 21 years, there would be a violation. This didn't actually happen, but the Rule Against Perpetuities, is only concerned with what might have happened. If this had been a testamentary trust, there would not have been a problem since the creation of that interest is the settlor's death. Coolidge also reserved the power to change the beneficiaries up until the time of his death. That didn't make the trust revocable, but it sort of gave himself a special power of appointment. That made him both the donor and the donee. When the youngest of Coolidge's grandchildren living at the time of his death turned 50, the trustee went to Court to determine the validity of the trust. The Probate Court found that the life income gifts were valid, but the gift of the remainder was invalid because had been a possibility that it would have violated the Rule Against Perpetuities. The trustees appealed. The Massachusetts Supreme Court found that the entire trust was valid. The Massachusetts Supreme Court found that where a trust contains two alternate conditions, of which the first might violate the Rule Against Perpetuities and the second which actually occurred, does not violate the Rule Against Perpetuities, the rule is not violated. The Massachusetts Supreme Court found that since Coolidge retained a special power of appointment, he could have changed the trust at any time up until his death. While it could not be known if the trust would violate the Rule Against Perpetuities when it was executed, Coolidge had the power to monitor the situation and edit the terms of the trust if another grandchild had been born. It was only at the time of Coolidge's death could it be definitively known whether the trust would violate the Rule Against Perpetuities. Coincidentally, Coolidge's death was also the time when his power of appointment ceased to be exerciseable. Therefore, the facts used to determine whether the trust would violate the Rule Against Perpetuities, should be determined at the time the power of appointment ceased to be exerciseable, not the time when the trust was executed. This is known as the Second Look Doctrine. Coolidge could have avoided this by having the trust vest at the death of the last survivor living "at the creation of this instrument," as opposed to "at the time of my death."