Faithful butler, 37 years old, to the Griplings and sidekick to Blake, Winston (voiced by John Kassir) is more of a fatherly figure to Courtney and Blake than Prescott ever was. He has never married and has no children and sees the Griplings as his surrogate family rather than just his employers. He is often involved in Blake's latest schemes to ruin/befriend Carl Foutley (who he called "Master Carl").
Winston is a devoted butler and he cares about the Griplings' well being. In Season of Caprice, he tried to talk Courtney out of going to Camp Caprice for the summer but to no avail. In Dare I, Darren?, he had to be by Blake's side when he got his tonsils removed. In Hello Stranger, he assisted Courtney as she was displaying her talent in the school auditorium. He also appeared at Courtney's graduation in Butterflies Are Free. This shows that, to some degree, he does care for Courtney and Blake like they were his own children. Winston does good a job in assisting the Griplings and the family is appreciative of his work.
Winston is a calm person and does his best to do a good job. He loves being a butler for the Griplings.
He is generally seen wearing an all black suit along with his hat and belt buckle. He also wears a red bow tie. The shoes he wears are also black.
Claire Gripling: He gets along with her very well. In Trouble in Gal Pal Land, he helped her make Hoodsey into a street urchin so she could become president of her country club. He helps her out when he's needed.
Blake Gripling: He looks after Blake more than he looks after Courtney. This is possibly because Blake is younger while Courtney has a social life and hangs out with Miranda. Whenever Blake needs assistance, Winston is always there to help him out.
Courtney Gripling: He looks out her best interest. As Ginger was giving her graduation speech in Buttetflies Are Free, he can be seen crying tears of joy. This shows how happy he is for Courtney as she graduates from middle school.
Carl and Hoodsey: He is shown be nice and respectful to them. He will occasionally address them as Master Carl and mispronounce Hoodsey as Master Woodsey.
- In Detention, according to Blake, Winston attended Harvard law school.
- He fills the role as the unofficial male figure in Courtney and Blake's life due to Prescott's absence.