I wish he'd share that loophole then. CRA won't even let you move shares between you and your spouse.
http://www.taxtips.ca/personaltax/investing/taxtreatment/shares.htm
If shares (or other capital properties) are disposed of at a loss, this is considered a superficial loss, and may not be deducted as a capital loss if:
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the shares (or identical shares) are repurchased within 30 calendar days (before or after the disposal) by you, your spouse, or certain other persons affiliated with you, and
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you, or a person affiliated with you, still own or have a right to buy the shares 30 calendar days after the sale.
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A person affiliated with you includes, but is not limited to:
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your spouse or common-law partner
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a corporation controlled by you or your spouse or common-law partner
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after March 22, 2004, a trust, including an RRSP, TFSA or RRIF, of which you or a person affiliated with you is a beneficiary
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