BruinLVGA
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I doubt he goes to the Bruins. Their management are not very bright, I can't see a Harvard grad wanting to work for a bunch of knuckle draggers. I also think the Leafs are unlikely, you don't often see Americans willingly leave the country all else being equal. I think his #1 choice would be Washington, his degree is in government and lots of his Harvard connections would end up there. I think he just sees the NHL as a temporary gig for a decade or so, and has aspirations for his career afterwards that will factor into where he signs.
I love this narrative. À la Michael Crichton. I would buy your fiction book. Gotta put a couple unexpected plot twists though, otherwise it becomes too linear, too easy to forecast.