WESTLEY OH MY GOD LOOK HE IS DOING YOU A SOLID HE HASN'T EVEN ARRESTED YOU YET.

I am 1,000% down for this. Are you comfortable with James side-eying him pretty damn hard if he tries to infiltrate the crew in disguise? Westley already sent up some warning bells in their first conversation, and James has made sure to familiarize himself with the piratical population of Tu Vishan. Plus, he's served on two pirate ships recently, so he knows some of the trade.