Character Analysis
Winston (or Winnie as his enemies call him) is an old man who hasn't really learned much. Unlike Robert (who used to be good at poetry) or Xiu Xiang (who is good with technology), Winston doesn't really have much in the way of skills. And now that he's back in the game (like Robert and Xiu, thanks to medical technology), Winston wants to rocket back up to his former position as Dean at UC San Diego.
Robert hates Winston at the beginning and, as much as we hate to agree with Robert, we kind of have to here. Winston wants to regain power in the school—but why? It's not like he has any huge projects or goals besides getting his power back. Even when Blount joins the anti-Librareome Project group, he joins because it looks to him like "a magnificent shortcut" (12.3).
So Winston is another of the old people who we can see as a contrast to Robert: Robert wants his poetry back and then for people to respect him—Winston just wants respect and power for its own sake. (There's something pure about that. Purely self-centered, but pure.)
And like Robert, when Winston fails to get what he wants, he seems to make some peace with it—and with Robert. When Winston goes to see the high school composition demos, he even congratulates Robert on the poetry (34.7). So when we hear in the epilogue that Winston has taken an entry-level job at the university, we shouldn't feel bad for him (Epilogue.52). We should feel hopeful that he's willing to try something new.