A.P. Toldo Holding Corporation v. The Queen, 2014 DTC 1042 [at at 2787], 2013 TCC 416 -- summary under Paragraph 20(1)(c)

By services, 28 November, 2015

The taxpayer was a holding company for various direct and indirect subsidiaries which carried on an operating business. To resolve a shareholder dispute, it purchased for cancellation the shares of a corporate shareholder holding 12.5% of its shares in 10 tranches, each occurring on the same day. The consideration for the first five tranches was paid in cash, and for the last five tranches was paid by the issuance of an interest-bearing $20 million promissory note. The promissory note was repaid on its maturity, one year later, in cash, some of which was borrowed money.

D'Arcy J found that the taxpayer had not established that the interest on the promissory note was "paid in respect of money borrowed in the course of a money-lending business" (para. 58). Accordingly, the interest was not deductible under s. 9.

Nor could the taxpayer deduct the interest under s. 20(1)(c)(ii). This was not "an exceptional fact situation" such as in Penn Ventilator, which justified a finding of a qualifying indirect use of the shares purchased for cancellation (para. 71). Instead, the taxpayer's stated capital and retained earnings were nominal, and there was no evidence that the settled dispute had threatened its sources of income.

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no retained earnings or stated capital
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