You know him as Squints from “The Sandlot,” but he was also Dean’s roommate in Gilmore Girls, Chauncey Leopardi recaps Season 3 E14 “Swan Song” with Scott. 

Chauncey shares a theory on Jess’ punk behavior in this episode. Is he really self sabotaging things with Rory, or is there more going on beneath the surface?

Plus, find out his surprising close connection to Milo Ventimiglia!