Minister of National Revenue v. Sissons, 69 DTC 5152, [1969] S.C.R. 507, [1969] CTC 184 -- summary under Debt/ receivables

Following the purchase by the taxpayer of two companies on the verge of bankruptcy ("Sonograph" and "Semco"), the acquisition by him of debentures of Semco at a discount, the transfer by his company of its business to Sonograph, and the repayment by Sonograph of indebtedness owing by it to Semco after the realization by Sonograph of profits from the transferred business, the debentures owing by Semco to the taxpayer were repaid for their principal amount, giving rise to a profit to the taxpayer. This profit was found to be realized in connection with an adventure in the nature of trade given that those debentures could not be considered to have been acquired for income and given that the profit arose at least in part from his efforts as a businessman.