The taxpayers, who were holding companies for partnerships that had recently agreed to sell their farmlands to third parties, were approached by an independent third party (WTC), who proposed that they transfer their partnership interests on a rollover basis to respective Newcos which, after the closing of the farmland sales and after WTC had taken brief de facto control of those subsidiaries and purported to generate “tax shelter” for them, would be sold by the taxpayers to WTC for cash sales prices that reflected a premium over the cash sales proceeds from the farmland sales. Such premium reflected a sharing (on a 46/54 basis) of the purported (but bogus) elimination by WTC of the Newco’s tax liability from the sale.
S. 160 clearly applied to the extraction of the cash by WTC from Newcos in order to fund its payment of the purchase price to the taxpayers. At issue was whether the payment of those cash proceeds by WTC, in turn, to the taxpayers also occurred pursuant to a transaction between persons not dealing at arm’s length, so that there could be a further s. 160 tax debt transfer to the taxpayers. In so finding, Noël C.J. stated (at paras. 81, 86):
[B]ecause they were splitting amounts earmarked to pay a tax liability that was bound to become a tax debt rather than their own money, the resulting split does not provide the assurance that it reflects an ordinary commercial dealing between parties acting in their separate interests. Specifically, the tension that provides that assurance did not exist to the extent that it would had the parties been dealing with their own money. …
Further, once the respondents were swayed to buy into WTC’s plan by the thought of turning an unexpected profit out of their crystallized tax liability through what they viewed as a risk-free exercise, they became the instruments through which WTC, acting as the sole mastermind, would lay its hands on the $1.3 million [equal to the tax liability], isolate it with the remaining cash in the subsidiaries and share it with the respondents in the proportion that it imposed.