RE: Share TransferI believe that the transfer would need to occur at cost and that any future capital gains would attribute back to McDonald anyways.
However if he transferred them at FMV then he would immediately recognize a capital gain and he can offset past capital losses, but his wife needs to pay for the shares with her own money or he can lend her the money at commercial rates. I believe this is the scenario that makes the most sense, he is trying to take advantage of past capital losses he had by selling the shares to his wife @ FMV.
The other transfer at cost would not be advantageous at all since the capital gains would attribute back to him anyways.
amartino85