@IMACOP He meant to lose from the start but its not the courtesan that is his deciding (to lose) factor. Its the poison.
Mao Mao "owned" him because of the mind games she played. She intended for him to forfeit the match from the start and set up a condition where he had no choice but to forfeit. Rakan had three choices.
1. Don't play.
2. Win
3. Lose
Regardless, he would never obtain Mao Mao.
The match ended before it began.
@Mivas The guy has a face recognition problem, not a smell recognition problem. He knows it is liqour and he is super lightweight. In other words, he knows he lost before the match even started.
@Luke_chase The reason why he even bothered going through with the first two matches is probably because he wants to "spend quality time with his daughter".
@Cidolfas I read the WN too. Iirc she never said it was liquor and even Jinshi did not pick up on the smell. So Rakan probably didn't know as well.
Hope one of these days, we can see a Mao Mao cameo in a final fantasy game. Even if it is just a corner nameless background NPC with no lines like one of the million "tourists" in FF15