Bogans attended DeMatha Catholic High School in Hyattsville, Maryland, and was a First-Team All American in his senior year. He was coached by Morgan Wootten, leading DeMatha to a 34-1 record and a number three national ranking in 1999. He was recruited by the University of Kentucky, and was a four-year starter for the Wildcats under coach Tubby Smith. In his senior year at UK, he led the 2002-2003 Wildcats to a 16-0 sweep of the Southeastern Conference and the SEC Tournament title, finishing with an elite eight run in the NCAA Tournament.
Bogans was chosen with the 43rd pick in the 2003 NBA Draft by the Milwaukee Bucks, but was traded to the Orlando Magic on Draft Day. Bogans started in half of the games he played in his rookie season, averaging 6.8 points, 4.3 rebounds and 2.9 assists per game. Despite his rookie success, the Magic elected to trade Bogans to the Charlotte Bobcats in exchange for Brandon Hunter on November 1, 2004.
Bogans continued his development as a player for the Bobcats in the 2004-05 season, starting in 42 of his 76 games and averaging 9.6 points per game.
On February 9, 2006, Bogans was traded to the Rockets for Lonny Baxter. Interestingly, Chuck Hayes and Gerald Fitch, Bogans' former teammates at the University of Kentucky, along with himself, were all at one point members of the Rockets (Fitch has since been released).