A graduate of Georgetown University, Cherwin is the current Executive Director of the New York State Democratic Campaign Committee. Cherwin got his start in politics on Al Gore's 2000 presidential campaign serving as finance director. Cherwin went on to assist Gore in his post-political life, including "An Inconvenient Truth". In December of 2009, Democratic Conference leader John Sampson tapped Cherwin to replace Malcolm Smith appointed director Rob Calentine.