This is the sharpest mechanic on today’s page and it is almost perfectly non-transferable to Canada. It needs two American things at once: a grantor trust whose settlor can swap assets in and out without tax consequence, and a basis step-up at death that makes it worth doing. Canada has neither. The rule here is the opposite — a deemed disposition at fair market value immediately before death under s.70(5) of the Income Tax Act, plus the 21-year deemed disposition that most family trusts face. Pulling appreciated assets back into a Canadian estate makes the tax worse, not better.

The Canadian analogue to the goal — keeping future growth out of your own hands — is the estate freeze: exchange your common shares of the operating company for fixed-value preferred shares and let new common shares be issued to a family trust, so growth from that date accrues outside your estate. The freeze is a structure to put in place before value accumulates, not after a liquidity event, which makes the timing question the live one rather than the mechanic itself.