Crowle "Smiles" Strathmill was born in Crow's Foot, the son of working girl and a member of the Crows while Madrin was still in charge of it. Dark-haired, handsome, if a bit dirty and wordy, Crowle was raised amongst the Crows all his life. The life of the scoundrel was the life he was most accustomed to and when he was sixteen years old, he joined the Crows as an official member. It was the proudest he had ever seen his father been.
Life had always been up and down for Crowle but unlike his father, who just accepted things as they were and worked to make them better, Crowle wanted to learn why things were the way they were. He wanted to see how a favor owed could damn a gang to die while another word might be able to save them. He studied carefully, learned what he could, and began to follow the trade of the Spiders. What good was it to spill blood if you didn't know why you were doing it?
His father was killed by the Billhooks a few years after that in retaliation against the Crews taking more territory from them and it was during the massacre afterwards that he was given the nickname "Smiles". Crowle was usually a cheery, friendly man but when he learned his father was murderd and made an example of, the smile wouldn't leave his face. When he lured those responsible into the clutches of the Crows, his smile didn't disappear as he cut the man's eyes out and left them as a warning to know their place. The rumor had it then that if you see Crowle smiling, it either means you're in for a party or someone is going to die.
After his betrayal at the hands of Salia and his time locked away within Ironhook Prison, Smiles came out to see how the world had changed. His mother, despite the care that the Crows formerly gave her, passed away without medicine after there was the sudden change in leadership. Lyssa approached him with an offer to rejoin the gang but he was disgusted with her betrayal and refused, especially hearing how she had help broker peace between them and the Billhooks and how they had forgotten to take care of his ailing mother while he was serving his time.
Without a crew to call his own, Smiles has relied upon Jeren and the few contacts he has left to keep an ear out for any up and comers. Maybe it was time he stopped being the loyal follower, the gifted helper, and started calling the shots himself? All he needed was a crew to get behind him and he'd lead them to bloody glory through Duskwall.