Jack Likes His Drink
Our next customer, Jack Adams, won't be the pushover that Harry was. He spends all day drinking with his friends, tough pirates all of them. Let's not use force this time, could get ugly.
See if you can use his drinking habit to your advantage. There's only so much alcohol someone can handle before passing out.
Maybe one of the bar wenches will be of assistance. Once he's out, see if you can slip your hand into his pocket and get what's mine.