Quote:
Originally Posted by BigNumbers
You cannot sell to a spouse or family member as that is not at arms length. Selling and buying a different class of share is likely not kosher under GAAR. Not likely to get caught, but if you did something to avoid tax you are a target for GAAR.
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This would be an interesting case. My initial thought was that this shouldn't be GAAR-able because it would amount to CRA pointing to an alternative purchase you would've made that would have resulted in tax, which is a non-starter for a court. However, upon further thought, there's clearly a tax benefit (the loss) and the sale was primarily motivated to realize the loss rather than to dispose of the security, so it does sound kinda like a win for the minister.