Sherwin is an elderly bellboy in Pierpont Inn., working there for almost his whole life.
When Sam and Dean arrive at the hotel, Sherwin leads them to their room and insists on carrying their things. He tells the brothers a bit about the Inn.'s past as once looking like a palace. His parents also used to work here.
Sherwin also works as a bartender downstairs. When Dean comes to the bar, he tells him more stories about the Inn's past.