- “I LOVE SUPERHEROES! The powers, the costumes, the mythic struggles!”
- ―Winston expressing his love for superheroes
Winston's parents were big supporters of superheroes. His father, the CEO of a small electronics company called DevTech, was good friends with the heroes Gazerbeam and Fironic, and possessed special phones that acted as direct lines to them in case of emergency, which he loved showing off to the family's friends and associates during parties. Not long after Supers were banned, a pair of robbers broke into the Deavor mansion. Winston, his sister Evelyn, and their mother hurried to the safe room while their father headed to his direct lines to call for help, but received no answer. The robbers discovered the Deavor patriarch and shot him. Winston's mother died a few months later from a broken heart.
Winston always believed that if the Supers had been allowed to continue to help people, his father would still be alive. When they grew up, Winston and his sister inherited the company, and built it into one of the largest telecommunications corporations in the world. They also continued their father's support and decided to take it to the next level, kicking off a campaign to help the Supers' cause. Since the government shut down the program that helps supers, the time was right for the Deavors to step in.
Ultra-wealthy, savvy and suave, Winston goes big in everything he does, including his plan to bring back superheroes. All he needs is a hero (or three) to help him change public perception and eventually make them legal again. His reason for choosing Elastigirl to lead the campaign was because she tends to solve crimes with far less damage than Frozone or her husband, based on cost-benefit analysis by his sister.
Winston believes that the super banned law is what kept supers from coming to his parents' aid, and from stopping the robbers that had broken into their home and killed his father, if they were allowed to go on patrol, answer calls of help and to do their job. Not long afterwards, his mother would die of heartbreak as a result. Which is why he set himself the task to make them legal again, so no one else would go through what he and his sister have.
Winston is determined and confident in what he does. He is a brilliant businessman, and his suavity and charm makes him brilliant at connecting with people. He also seems to be very cosmopolitan, seeing that he convinced Supers from all over the world to leave their old life and join him in his cause. He truly believes that he can use his wealth and power to make the world a better place for everyone.
Despite his enormous amounts of wealth and business connections, Winston seems to be down-to-earth and is able to sympathize with the Supers. Although at first, it seemed that he had some other nefarious — and hidden agenda that is secretly motivating him — this was proven not the case. His sister, Evelyn, revealed that she kept her "Screenslaver" identity a secret because she knew that Winston's strong morals would never permit him to go along with her unscrupulous ways. He later demonstrates this morality when, upon realizing his sister's true intentions, he refuses to escape with her, despite her being the only family left for him. Deciding to reboard the ship that will crash into the city, he risks his life to try and free all the Supers and ambassadors from Evelyn's technological hypnosis, all by himself, and get them to safety, greatly showing a selfless side to his personality. Presumably, Winston also later explains his sister's activities regarding this crisis to the authorities to ensure her arrest and that the Supers are properly credited for their resolution.
- “If we want to change people's perceptions about superheroes, we need you to share your perceptions with the world.”
- ―Winston to Frozone, Elastigirl and Mr. Incredible
Winston first appears during the beginning of the film where he notices the Parr family and Frozone preparing to stop the Underminer's machine from reaching the Town Hall in which the superheroes were unable to stop the out-of-control machine and causing damage towards the Town Hall. After the Superhero Relocation Program is shut down, Frozone, Elastigirl, and Mr. Incredible encounter Winston at DevTech. Meeting him, Winston then explains that after the city of Municiberg has no superheroes for years, he plans to bring back the superheroes to Municiberg so that they can regain their legal status. When Winston plans to do so, he brings Elastigirl to the city of New Urbem where she stops a newly-opened train being controlled by the Screenslaver. He is later seen along with the Ambassador and her daughter Evelyn during the scene where Elastigirl is ready to be interviewed about rescuing the passengers from the train, in which the interview is suddenly taken over by the fake Screenslaver.
Elastigirl then meets Winston in his office where he tells her that the Ambassador made a big speech about superheroes which should be kept legal after saving her from the out-of-control helicopter she is at. Winston then tells her that DevTech will have a conference at sea where she is happy that Winston's plan will make Supers around the world legal again. Elastigirl then explains that she had not caught the fake Screenslaver yet even though she saved the Ambassador. Winston's sister Evelyn tells her brother to show her the other Supers in Winston's office where Winston and his sister watch Elastigirl mingle with the Supers.
Later when Elastigirl captures the fake Screenslaver, Winston then celebrates Elastigirl's capture and plans to bring DevTech on a luxurious ship where the supers would regain their legal status. When Elastigirl, Frozone, and Mr. Incredible are brainwashed with Hypno-goggles along with the other superheroes and after Dash, Violet, and Jack-Jack get rid of the Hypno-goggles, Winston suddenly confronts his sister Evelyn for betraying him about making superheroes legal. Later after Elastigirl captures Evelyn when she escapes and when Evelyn gets arrested for her crimes, Winston makes all the Supers legal once more, making the superheroes regain their legal statuses.
- 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.
- Winston is basically a good version of Syndrome a.k.a. Buddy Pine from the first film for different reasons:
- They're both wealthy people, though they obtained and used their wealth differently (Buddy obtained his wealth through more shady means by selling his technology to oversea terrorists and he used his money to own a private island and make gadgets that hurt people and supers while Winston obtained his wealth more honestly through his father and inherited his company, which was more well-know and he used his wealth to benefit people and supers.)
- They're both fans of supers but they handle their fandom differently (Buddy was obnoxious to supers (more specifically Mr. Incredible) as he did not honor Mr. Incredible's wish to leave him alone and this immaturity soon led him down the path of villainy where he killed off the supers while Winston was more mature and respectful to supers and genuinely wanted to help them.)
- This may have to do with the fact that Buddy was younger and lacking in mature functions while Winston is an adult and fully capable of being mature.
- They were both betrayed by a female companion they had for alternate reasons (Mirage betrayed Buddy out of a good conscience and Evelyn betrayed Winston out of a spiteful dislike to supers.)