Giles Winslow Jr.

Giles Winslow Jr. is the main/sole antagonist of the 2018 film Christopher Robin which is based on the Winnie the Pooh franchise. He is Christopher Robin's boss at Winslow Luggages.

Film role
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, Tigger, Piglet 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, giving employees paid leave, and selling their luggage to everyday people to increase demand, instead of laying off employees. 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.