The 6 ft 9 in (2.06 m), 235 lb (107 kg) forward was selected directly out of high school by the Los Angeles Clippers with the third overall pick in the 2000 NBA draft.

Miles' playing career nearly came to an end when he was released by the Portland Trail Blazers in April 2008 after two years away from the court following microfracture surgery on his right knee.

Before declaring to enter the 2000 NBA draft, Miles had signed a National Letter of Intent to play for the St. John's Red Storm men's basketball team, alongside fellow top recruit Omar Cook.

Mike Jarvis, the head coach for the Red Storm at the time, has stated that Miles' commitment significantly helped obtain Cook and the other incoming freshmen from the recruiting class.

His debut game was played on October 31, 2000, in a 94–107 loss to the Utah Jazz where he recorded eight points, seven rebounds, two assists and two blocks.

[1] For the next two seasons Miles, Quentin Richardson, Corey Maggette, Lamar Odom and Elton Brand entertained fans with their exciting, high flying style of play.

When Cheeks left the room to see Blazers' general manager John Nash, Miles ran behind him shouting, "That's right, run to your daddy.

[8] The examination determined that Miles' knee injury was severe enough to be career-ending, prompting the Blazers to request waivers for his release on April 14, 2008.

[7] On August 22, 2008, the Celtics signed Miles to a non-guaranteed contract offering him a chance to earn a roster spot at training camp.

[13] After sitting out his ten-game suspension, Miles made his season debut with the team on January 4, 2009, playing the last 1:46 in a 102–82 win against the Dallas Mavericks.