"[Sam is one of] high-school boyfriend[s], and the first in a long line of men to do Taylor wrong: He allegedly cheated on her shortly before her first album came out. (Thus making him the only one of these dudes who can claim he didn’t know what he was getting into.)" Theres no knowing of where Sam is in life right now, however, "His Twitter is locked, which means he’s probably tired of being asked to comment for stories like this one." -vulture.com
Although a stretch, Taylor could've written Picture To Burn about Sam because of her anger towards him and him cheating
Alluding to the speculated cheating, Sam is likely the cause and inspiration for Should've Said No, since it's a song straight up about a boy cheating on Taylor