Giles Winslow Jr. is the main antagonist of the 2018 film, Christopher Robin. He is Christopher Robin's ex-boss at Winslow Luggages.
Role in the film
With Christopher Robin's company hitting hard times, Giles Winslow Jr. tells him to decrease expenditures by 20%, largely by choosing which employees to lay off, and to present the necessary paperwork on Monday. This forces Christopher to forego his plan of traveling with his family to his countryside cottage in Sussex for the weekend before the summer ends. Christopher finds Pooh in London and brings him back and finds the rest of his friends.
One morning, Christopher, who realizes that he fell asleep, leaves the Hundred Acre Wood so he won't miss his presentation. Pooh realizes that Tigger has removed Christopher's paperwork in drying his briefcase, so Pooh, Piglet, Tigger, and Eeyore decide to travel to London to give it back. Christopher is about to present his plan, but realizes that his briefcase is filled with items given by Tigger, so he left. After he reunites with his wife and daughter, he comes back and improvises a new plan involving reducing the prices of luggage to sell to everyday people to increase demand and giving employees paid leave, instead of laying them off. Winslow Jr. dismisses the idea, but his father Winslow Sr. warms up to it. Christopher points out Winslow Jr. hasn't been doing his part in helping with the plan, having been golfing all weekend, and Winslow Jr. is humiliated. Winslow Sr. agrees to the plan, and Christopher decides to spend time off with his family.
Winslow is the first real character in a Winnie the Pooh film to be a genuine antagonist; other films featured either characters that were imaginary, characters that were initially believed to be antagonistic, or did not feature an antagonist at all.