- "--I can't. Because I didn't see it. Neither did anyone else. So, when you fight bad guys, like today, people don't see the fight or what led up to it, they see what politicians tell them to see. They see destruction and they see you."
- —Winston about why supers are illegal.[src]
His role in the film is as as leader of DevTech, and is interested in the legalization of supers, and wishes for them to return to the spotlight.
In this film, he hires Elastigirl to show that Supers are beneficial for society since she does less collateral damage than Mr Incredible and Frozone. Bob is surprised and a bit saddened that he was not considered. Deavor senses Bob's dismay to some degree, and promises that should Elastigirl succeed, this will pave the way for his and Frozone's return.
Behind his back however, his sister Evelyn intends to ruin his plans by ruining the reputation of Supers with the Screenslaver and by hypnotising supers with hypno-goggles so that they can ruin their own reputation. Winston hosts a party on the Everjust where an accord supporting the legalisation of supers is signed by several international ambassadors including Ambassador Selick. Evelyn hypnotises everyone there so that her plan can succeed. However, Violet, Dash and Jack-Jack arrive to free the supers, foiling her plans. Winston is freed from his hypnosis and meets up with Evelyn, but figures out she has done something bad and decided to help everyone else on the superyacht, freeing them by smashing the screen with a chair. After the supers save the yacht from crashing onshore, he thanks them for saving everyone on board and his sister.
- In an early script of Incredibles 2, Winston was a greedy villain beside his cut brother, Nelson Deavor. He was motivated mainly by financial gain for his media company. But Odenkirk's performance was so genuine that Winston was turned into a good guy who wanted Supers to return because he thought the world would be better that way, regardless of his own gain.
- He bears a slight resemblance to his voice actor, Bob Odenkirk, specifically his character Saul Goodman from the television series Breaking Bad, as well as its spin off, Better Call Saul.
- He bears a strong resemblance to his late father when his father was young man.