Chesseley was born in raised in Raleigh, NC and have been a part of this community for over 40 years, attending Washington Elementary School, Martin Middle School, and graduating from Athens Drive Senior High School in 1992. Chesseley attended North Carolina State University and graduated in 1997 with a B.A. in Political Science. In 1997, at 23 years of age, he was a candidate for Mayor of Raleigh. Currently he serves as Vice Chairman for the Raleigh Housing Appeals Board.
Chesseley graduated Cum Laude from the University of the District of Columbia – David A. Clarke School of Law and served as Executive Notes Editor for the David A. Clarke Law Review. He taught Criminal Law and Procedure and Legal Ethics at both Southeastern University (2003-2005) and Bowie State University (2004). Prior to attending Law School, Chesseley was a teacher and student mentor part time at Bonner Academy, a program for troubled and/or disadvantaged teens.
Chesseley is a barred attorney in the District of Columbia and has practiced educational law for the past 13 years. He has conducted in excess of 100 due-process hearings under IDEA 1997/IDEIA 2004 in the District of Columbia. He also worked as Defense Counsel for juvenile delinquents and status offenders in the District of Columbia from 2009 until 2014. Chesseley was a Hearing Officer for Guilford County Public Schools from 2006 until 2009, a Hearing Officer for the Employment Security Commission of North Carolina from 2005 until 2006, and served as a Legislative Intern for the Judiciary Committee in the Summer of 2002 under the supervision of Ted Calo in the Honorable John Conyer’s office.