Mr. X holds 100 Class A voting participating shares of Opco with a fair market value of $5M and nominal adjusted cost base and paid-up capital. He incorporates Holdco whose shares have nominal fair market value, adjusted cost base and paid-up capital and exchanges his Class A shares of Opco for preferred shares of Opco with the same FMV, ACB and PUC as the exchanged Class A shares. Opco issues Mr. X 100 Class A shares for nominal consideration and also issues 100 discretionary dividend shares to Holdco. In order to limit the net asset value of Opco to $5M (i.e., for creditor-proofing purposes), Opco annually pays dividends of $500K on the discretionary shares held by Holdco.
CRA stated (TaxInterpretations translation):
Mr. X may not be entitled to the capital gains deduction provided in subsection 110.6(2.1) in computing his taxable income for a taxation year by virtue of paragraph 110.6(7)(b), if the gain from a disposition by Mr. X of the new Class A shares of the capital stock of Opco was part of a series of transactions or events under which Holdco acquired discretionary dividend shares of capital stock of OPCO for consideration well below their FMV at the time of acquisition.