Bro... Kane and Olivia aren't competing... Kane cannot 'win' the Gambit.That doesn’t explain why Callista wants Olivia to win the gambit instead of her own son. She only says that it will help Kane. The only two people who have told him he can’t take the company are Alessandra and Kitty, but I think Kitty has her own agenda for him to take the company. I believe she is still loyal to Alexander, even after his death, and wants him to be the next Alessandra.
Olivia, Juliette, and Dominique are competing to 'win'... Kane is not.
Kane's testing has nothing to do with him winning the Gambit or not. Only what happens after the Gambit is successful (if it is).