A year 2000 graduate of the University of Wisconsin-Milwaukee, Sherwin began his professional career as a community organizer with the YMCA Community Development Corporation. In 2002, Hughes was offered a position as field representative for Congressman Tom Barrett (WI-5) In 2004 Hughes was hired as a statewide constituency director for the Kerry/Edwards campaign. After the presidential race of ’04, Hughes was brought on as a business analyst in Milwaukee mayor Tom Barrett’s department of administration—where he certified minority businesses for participation on city contracts.
In 2005, Hughes was appointed as Governor James Doyle’s sole designee on the Wisconsin State Elections Board. In 2007, he would become chair of that nine person, bi-partisan body. Sherwin was the only African American in state history to serve in the administrations of both an incumbent mayor and governor simultaneously In 2006 Hughes incorporated STH & Associates, LLC a political consulting firm. In 2008 Hughes became communications director for Wisconsin state senator Lena C. Taylor. In 2010, Hughes became Wisconsin state field director for Democrats for Education Reform. July 2012, Hughes became the host of “The Forum” a political talk show on WNOV in Milwaukee.