A was one of eight individuals holding all of the shares (of a single class) of Opco. (Specifically, each of A, B, C and D held 18.75%, and each of E, F, G and H held 6.25%, of the Opco shares.) A, B and C) were the group with de facto control of Opco.. A, B and C formed a group of persons who had legal (de jure) control of Opco.
A sold all of A’s Opco shares to Holdco for non-share consideration equal to the fair market value of the shares disposed of. B, C, D, E, F, G and H held all the Holdco shares (with each of B and C holding 23%, D holding 22%, and each of E, F, G and H holding 8%).
CRA confirmed that s. 84.1(2)(b) did not apply to deem A to not deal at arm's length with Holdco, and went on to note that it was a question of fact whether A did not deal with Holdco as a general matter.