Winston comes to Liberty High to get the answer to who actually killed Bryce so he can get justice for Monty. He inserts himself into the core friend group by first befriending Tyler and then falling for Alex, but he never quite makes it into the group.
He decides that Jessica is the one who killed Bryce and tries to get someone to admit to him that he's right, but everyone keeps telling him he's wrong. He even threatens them with Bryce's tape, claiming that Jessica had to have done it. Alex finally admits to him that he did it and Winston is welcome to do whatever he wants with that information.
In the end, Winston gives Bryce's tape to Alex, admitting that he loves Alex and is giving up on revealing the details of Monty's death.