Wynter was a kind of pacifist, fighting only if he really had no other options. He preferred to avoid confrontations by using words. This was also because he was very confident about his fighting skills. Wynter greatly disliked the Red Wizards of Thay.
Wynter was born in Thay. His father treated his slaves very harshly, and Wynter grew disgusted by this practice and abandoned his home. After some outlaws robbed him, he met Galvin, who helped him to recover his goods and afterward inducted him into the Harpers.
In 1362 DR, he and Galvin were instructed by Brenna Graycloak to infiltrate Thay to uncover some plots. During the mission, Wynter posed as a buyer and managed to free a group of slaves. They discovered the evil plans of the Zulkir Maligor and, thanks also to the help of the lich Zulkir Szass Tam, defeated him.