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 surogate 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").
- 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.