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Like a dweeb, I went back and listened...Tom said "weeks ago." I'm not sure how time goes on this show, so not sure if Ivy Week was two days before the episode or two weeks.
I bet it doesn't have anything to do with Dartmouth--Daddy's in some sort of financial/legal trouble and needed the money. That's also why he's trying to get him to follow in his footsteps, since it would be easier/cheaper/etc to do so if the Captain gets into any real trouble.
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