Giles Winslow Jr.

Giles Winslow Jr. is the main antagonist of the 2018 Disney film Christopher Robin. He is Christopher Robin's boss at Winslow Luggage who is planning to lay off many of the employees purely for profit.

Biography
At the start of the film, Winslow is Christopher Robin's boss at Winslow Luggage, which is run by his father Winslow Sr. With the company on hard times, Winslow Jr. tells Christopher to decrease the company's expenditures by 20%. Specifically, he wants Christopher to decide which employees to fire, which would be a lot, and to present the paperwork on Monday. This kickstarts the plot of the film, with Christopher being forced to forego his plans to holiday with his family. At the end of the day, Winslow leaves to play golf.

After visiting his childhood friend Winnie the Pooh, Christopher goes back to work to deliver the presentation. However, Pooh discovers that Tigger removed the paperwork from Christopher's briefcase because he didn't know it was important. Having heard Christopher say that Winslow will "eat him for breakfast" if he loses the paperwork, and thinking that Winslow is a Woozle, Pooh resolves to get the papers back to him. His friends agree to help.

At the end of the film, Pooh and his friends, along with Christopher's family, almost get the papers to him, only for them to blow away in the wind. However, Christopher gets an idea from the only document he was able to retrieve and gives the presentation in front of Winslow Jr. and Sr.. He has the idea of lowering the price of luggage and sending the employees on holiday, because when people take holidays they buy luggage. Winslow Jr. scoffs at the idea, but Winslow Sr. likes the idea and approves it, in spite of his son's objections. As Winslow protests, Christopher points out that he has been playing golf all weekend. Humiliated, Winslow Jr. gives up as Christopher takes time off. As he leaves, Winslow points out that Eeyore (a stuffed donkey who is one of Pooh's friends) is looking at him and Winslow Sr. scoffs at his son.