Williams graduated from Germantown Academy in 1993 where he was in the same graduating class as Bradley Cooper. He then went to Villanova as one of the most highly touted recruits sounding a charge led by head coach Steve Lappas to restart bringing homegrown talent from Philadelphia to the Wildcats, which had been dormant for years under head coach Rollie Massimino. During his senior season, Williams led Villanova in scoring and assists with 17 points and 4.5 assists per game. Along with Tim Thomas, Williams would take Villanova to a regular season Big East title and a berth in the 1997 NCAA tournament where they lost in the Second round to California featuring future NFL All-Pro Tony Gonzalez.
Williams was in the Raptors' rotation under head coach Butch Carter and greatly improved as the starting point guard under head coach Lenny Wilkens in 2001. He started all 82 games for two straight seasons in 2001–02 and 2002–03. During the 2002–03 season, which was his best statistical season as a professional, Williams averaged 13.2 points and 5.3 assists per game. After missing a third of the 2003–04 and the entire 2004–05 season with a knee injury, Williams rejoined the lineup at the start of the 2005–06 season and played one game before the injured knee put him back on the injured list.
On July 26, 2006, Williams was waived by the Raptors to make room for free agent guard Fred Jones. Reports said both the team and Williams had reached an agreement that resulted in the Raptors only having to pay half of Williams's remaining salary.[4][5]
Los Angeles Clippers
On January 20, 2007, Williams signed a 10-day contract with the Los Angeles Clippers.[6][7] He was not signed to a second contract after the first expired after appearing in two games in limited action.[8]
On July 1, 2009, the Raptors announced the hiring of Williams as an assistant coach for the team.[9] This would mark the return of Williams to the organization since being waived by the team less than three years earlier.
On September 24, 2010, the Raptors announced that Williams would become the team's Director of Player Development.[10]
In June 2013 he was let go from his position with the Raptors.[11][12]
In September 2021, Rogers Sportsnet and the Toronto Raptors announced that Williams would take over the colour commentary duties on all Rogers Sportsnet broadcasts of Raptors games, replacing Leo Rautins on that network.[14]
^Thompson, Art III (January 30, 2007). "Clippers let Williams go". Orange County Register. Archived from the original on February 2, 2007. Retrieved May 29, 2020.