Lara's butler who is often seen at Croft Manor. He rarely plays any role in the game's plot, usually only seen in Lara's Mansion, in the 2nd and 3rd games he follows Lara around the mansion, carrying a tray with what seems to be blue mugs on it and often farts and groans. One of the secrets in the 2nd and 3rd game was the ability to lock Winston in a large freezer.
In Tomb Raider Chronicles, he sits around a table with various other friends of Lara as they recall Lara's past adventures. He tells the story of how Lara finds the Philosopher's Stone in Rome, while being stalked by Larson Conway and Pierre Dupont. He also tells how Lara stole the "Iris" artefact from Von Croy's company building.
In Tomb Raider: Legend he stands beside the fire place in Croft Manor and offers advice to Lara in cutscenes. He also appears in the manor level of Tomb Raider: Anniversary. He is voiced by Alan Shearman.
He appears during the Prologue level and the Croft Manor level of Tomb Raider: Underworld. When Lara finds that one of Thor's Gauntlets may be in her grandfathers grave, Winston reveals a secret passage in the "Tech Room" that leads to the Croft family Crypt. He, Lara, Zip and Alister investigate the crypt and find that below Lara's grandfather's coffin is a secret passage, which Lara then goes into to find the Gauntlet. Meanwhile Winston and Zip are attacked by a Lara doppelgänger sent by Natla and Amanda Evert to retrieve the "Wraith Stone" and Croft Manor is then set on fire. Winston and Zip then try to escape through the main door, when Lara appears. Winston stops Zip from shooting her after he mistakes her for the doppelgänger. Lara then tells the two to get out of the Mansion. Winston waits with Zip for the authorities when Lara emerges with Alister's dead body, who had been shot by the doppelgänger. Lara announces to the two she is leaving for Mexico to find Thor's belt and kill Natla. Winston is not seen again for the rest of the game.