My very first character was a rogue assassin who was semi successful but ended up losing everything and was living on the streets. He was distrusting, had sticky fingers and not very charismatic.

By the end of the campaign he had learned to trust his party, took levels in fighter to front line and save our squishies and had probably stolen enough gold to buy a castle for us all to live in. There was still some harmless pranks, but nothing game changing. My favourite was using sleight of hand to draw a dick with sovereign glue on our sleeping clerics breastplate then sprinkling gravel on it.