He has spent time with the Seahawks (2000–2001), the Jaguars (2002), NY Giants (2003) and the Raiders (2004) where he did not make the final roster cut. Charlton was cut by the Raiders in September 2004, and joined the Patriots in February 2005 for the 2005 season.
Charlton signed with the Winnipeg Blue Bombers of the Canadian Football League on October 13, near the end of the 2005 CFL season and, besides a break in 2007, when he attended the Detroit Lions training camp, has remained with the Blue Bombers.[2] He re-signed as a free agent with Winnipeg on February 17, 2009, after receiving a matching offer from the Hamilton Tiger-Cats.[3]
On August 2, 2010, Charlton was released by the Blue Bombers.
On October 19, 2010, the Montreal Alouettes signed Charlton to the practice roster.
Coached for Freedom High School in Orlando, Florida.
After guest coaching with the Calgary Stampeders and Edmonton Eskimos in 2012 and 2013 respectively, Charlton was hired as the defensive backs coach for the Ottawa Redblacks on December 20, 2013.[5] He was a coach with Ottawa for four years and won his first Grey Cup championship in 2016.
On February 6, 2020, it was announced that Charlton was joining the Toronto Argonauts as the team's defensive backs coach.[6]