The Democrats won the 2000 4A Oregon state championship, beating Tualatin 58–44, and capping a 28–0 season.

4 national ranking and several other players went on to play in college, such as Michael Lee (Kansas), Thomas Gardner (Missouri), and Brandon Brooks (USC).

After being named the Oregon 4A High School basketball player of the year as well as McDonald's Morgan Wooten National Player of the Year, Miles attended the University of Kansas, where he starred at the point guard position for the Kansas Jayhawks men's basketball team.

Miles signed in September 2005, as an undrafted rookie free agent with the NBA's Golden State Warriors for the 2005–06 season,[3] but was released in January 2006, before his contract became guaranteed.

In August 2008, Miles joined one of the three Euroleague teams from the Greek League for the 2008–09 season, Panionios.

[10] Following his career as a player, Miles was hired at the University of Kansas as assistant director of student-athlete development for the 2015–16 season.