The Top Stupid Things the Characters Do
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COTBP
Will: Hitting Jack with the oar, screwed up the whole thing.
DMC
Will: Agreeing to go out and get the compass in the first place. Even if he got it, who's to say he wouldn't find Elizabeth hanging from a noose anyway? You're looking for a pirate who has his own ship and can travel the world, so it could take months, years even, to find Jack. Not only that, but starting in Tortuga? The Caribbean's most "wretched hive of scum and villainy," to quote Star Wars? They'll just lie to you and steal the buckles off your shoes!
AWE:
Will: I don't know...trying to outwit about 3 pirate lords at the same time? Yeah, Will goes all piratey and it's great, especially with Beckett and Davy, but you don't trust Sao Feng to make a deal with you and you don't expect Jack or Barbossa to welcome you back with open arms. Thank goodness you're a blacksmith and you knew how to get out of the brig on your own or you might have been stuck waiting outside during the Brethren Court meeting playing with your Tomagachi.