Winston was the Croft family butler during Lara's childhood.
Winston was fond of Lara, the two often played chess together, and Winston constantly hid sweets for Lara to find.
Though he was of mild temperament, he did have limits and had no qualms about reporting Lara's misbehavior to her father, including an incident where the young Lara locked him in the walk in freezer.
At some point after Amelia's death, Winston refused Atlas entry into the manor to speak to Richard, claiming that Richard was heartbroken and not yet ready to see visitors, as he was blaming himself for her Amelia's loss.
It is unknown where Winston went after Lord Croft died, but he later returned to work for Lara after the events of Shadow of the Tomb Raider.
Winston was devoted to his service to the Croft family, caring deeply for both Richard and Lara.
- Lara locking Winston in the freezer is a reference to a game players would play in Croft Manor in Tomb Raider II and III, wherein players could lock the butler in the freezer, by waiting inside, and then rushing out and locking the door afterwards.