In 2004 Dentmon led his Carbondale Community High School team to a fourth place state finish, during his senior season. He was the top scorer in the 2004 state tournament in Peoria scoring 78 points in only three games. Dentmon led his team in points with 22.1 points per game accumulating 773 points over his senior season. In that same year, he was named to the Illinois Basketball Coaches Association All-State 1st team, the class AA All-Star 1st team and named the South Seven Conference MVP. \n', '

After originally committing to play basketball at Illinois State University in Normal, Illinois Dentmon decided to play another year of prep basketball at The Winchendon School in Winchendon, Massachusetts. The NCAA men\'s basketball academic qualifier rules would have sidelined him for one whole season in Normal, which influenced his decision to continue his prep career. Dentmon\'s efforts on the court and the classroom at The Winchendon School help him secure a scholarship with the University of Washington.\n', '

In his rookie year at the University of Washington, Dentmon started in 32 out of 33 games and was named to the All-Pac-10 freshmen team by the league\'s coaches. Dentmon had one of the most productive freshman seasons in University of Washington basketball history. He led the Huskies in both steals with 52, and free throw percentage (81.4%). He was also second on the team in assists with 3.7 per game. Dentmon helped the Huskies to a 26-7 record and their second consecutive NCAA tournament Sweet Sixteen appearance.\n', '

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