Either a curse from a demon, a lost bet or their own volition, Gamblers love the thrill of taking and losing gold.
Bet: starting at level 1 you can pick a die (d4-d20), if you get a roll of 11-20 you get a bonus on your roll and gain 1 gold per level of die (11=1 gold, 12=2 gold ect), but if you get a roll of 1-10 you get disadvantage and lose 2 gold for each level of die (10= -2, 9= -4, ect) Bribe: While in battle you can Persuade enemies to forfit by paying them in ritches, the higher the roll the less gold needs to be given make them forfit (1=20 gold, 2= 19 gold, ect)
(a) 20 Darts or (b) a Sickle (a) a Deck of Cards or (b) 6 Dice (a) a Burglar's Pack or (b) a Dungeoneer's Pack Leather Armor and Thieves' Tools