Harry knows it's a bad trade, he fully knows it, and even when being confronted by Cindy he can't refuse it because the offer takes advantage of 3 things. 1) His inability to refuse people well if at all 2) His automatic default to go for the thing that'll make people happy, namely both giving Saishu this victory and effectively causing him to lose even more, which will in the long run make the others happier when they place above him and 3) His flustered nervousness at Cindy cornering him on a subject he'd never been confronted on, thus making the likelihood of him refusing an offer, even lower.
Harry can't help but feel Cindy is right, as long as she knows he's not fully trying, he's ruining her enjoyment. But he didn't know how to play otherwise, and didn't have the ambitious streak needed for this sort of game. But he can't go on playing like this to make the others happy because it'd make Cindy unhappy. But he can't unpoison a game, it's too late to start playing for real, he'd already set up his downfall and even if he tried now it wouldn't tell Cindy that she'd fully earned her win over him.
He takes longer than it should to put the new popcorn in the bowl as he thinks of a way out of this. And when he returns to the table he's nervous and distracted, but quietly watching the game all the while. How was he supposed to play board games now?
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