Ready and Set.
*******
When Tommi got out of jail, the guard said "See you soon."
Within an hour, he was visiting his mom, arriving with a bag of groceries, but he soon popped off for an afternoon at the pub. He never unpacked the groceries, and his mom ended up eating alone that night, and so it was that by midnight Tommi was on the far side of town, playing cards.
He wouldn't win a lot at first: small bets, appear to drink more than he did, friendly and easy and folding often. That was enough to get Stumpy to trust him. The dwarf's name wasn't stumpy, but Tommi couldn't pronounce Stompi correctly, or he chose not to be able to. Stumpy was the fish, and by dawn he was hooked; and by the end of the week, he had sold his amor and his axe, and left Daggerford in shame. The only question was whether Tommi had been able to keep any of his winnings.
(1) Wisdom (Insight): [roll0] vs. DC [roll1]
to spot the mark, and determine the right way to waylay him in the coming days.
(2) Charisma (Deception): [roll2] vs. DC [roll3] (includes proficiency in cards)
to win the card games when the evening stretches on.
(3) Charisma (Persuasion): [roll4] vs. DC [roll5]
to convince players to drop their guard, and make it all seem friendly.
(Gambling requires Intimidation, which would be two less than the roll in (3); I don't have the stake though, so I think I'm technically doing something else; since both Pit Fighting and Gambling have the rolling target, I've adopted that. I've only added cards to one roll).
EDIT: Three failures. Looks like Tommi is back in jail.