In Black Or White, their conflict started after Winston publicly announced his belief that Drew was a bad school president. Later that episode, Winston confronted Drew, and Drew lost his temper, pushing Winston to the ground. By the end of the episode, they resolved their differences after Drew agreed to listen to what the students wanted before deciding on school events.
- They both had crushes on Clare Edwards.
- Drew had a conflict with Winston's best friend Miles Hollingsworth III.
- This conflict shares similarities to the conflict between Spinner and J.T.