The taxpayer planned to move to the U.S.. Although the capital gain on the shares of his wholly owned corporation ("PC") that would have arisen (under s. 128.1(4)(b)) on his emigration would have been sheltered for Canadian purposes by unutilized capital losses, there would have been no corresponding step up in the tax basis of his shares of PC for US tax purposes. In light of this issue, he sold his shares of PC (which held liquid assets) to his brother-in-law ("J.C.") in exchange for a promissory note, which was satisfied (within the following serveral months) with funds that J.C. extracted from PC (by first transferring his high-basis shares of PC to a "Newco" in consideration inter alia for a promissory note, which was repaid by Newco with funds which it, in turn, extracted from PC).
After finding that s. 84(2) did not apply to deem any portion of the sale proceeds to be a dividend, Hershfield J. found that s. 245(2) did not apply to produce the same result. The alleged abuse was that the capital gains, which enabled the use of the taxpayer's losses, arose from payments that, being funds from the taxpayer's own corporation, would normally be treated as dividend income. Hershfield J. stated (at para. 116):
Indeed, triggering capital gains to utilize capital losses is not discouraged by the Act in any way. Transfers to a corporation without a section 85 election can be used to realize capital gains as can transfers between spouses. There is nothing abusive about realizing capital gains for no other purpose than to utilize available net capital losses.
Furthermore, allowing capital gains treatment of the sale produced a "fair result" (para. 139), whereas "to deny a tax benefit to which he was entitled by an express provision of the Act [i.e., s. 128.1(4)(b)] because he achieved it by a different legally effectively means is, frankly, bizarre" (para. 121). Although the transactions entailed surplus stripping, "it is doubtful whether in an integrated corporate/shareholder tax system, a surplus strip per se can be said to abuse the spirit and object of the Act" (para. 101).