|Intimacy Level||Former Rivals; Acquaintances|
|Conflict Started||Black Or White (1315)|
|Conflict Status||Ex-Rivals, Good Terms|
In Black Or White, their conflict started after Winston publicly announced his belief that Drew was a bad 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.
- 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.