Memphis Grizzlies (2008–2009)
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. Though he worked out twice with the team and impressed with his health and attitude, he was waived on October 20, before the regular season started.
On December 13, 2008, Miles signed with the Memphis Grizzlies. 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. On January 7, after collecting only two rebounds and two blocks in nine minutes over two games, Miles was waived. On January 9, following a controversy over his re-signing, the Grizzlies signed Miles to a 10-day contract. The next game, against the Cavaliers on January 14, Miles played 14 minutes and exhibited some of the quickness and leaping ability he once possessed. He recorded 13 points on 4 of 6 shooting and making 5 of 7 free throws in a 102–87 loss. On January 30, 2009, the Grizzlies signed Miles for the rest of the 2008–09 season.
On July 9, 2009, the Grizzlies renounced their rights on Miles in order to save cap room.
Under NBA rules, if a team is granted salary-cap relief for a career-ending injury to a player who thereafter participates in at least ten games the next season, the salary cap relief is terminated, and the amount is added back to the team's salary cap ceiling.
On January 8, 2009, after Miles played six pre-season games with the Celtics and two before being released from a non-guaranteed contract by the Grizzlies, the Portland Trail Blazers threatened to sue any of the other 29 NBA teams that picked up Miles and played him specifically to adversely impact their salary cap and tax positions. In response, the NBA Players Association threatened to file a grievance against the Trail Blazers. After a directive from the NBA Commissioner's office the next day declaring that any team could sign Miles and the League would approve the contract, the Memphis Grizzlies re-signed Miles on January 10, 2009, to a 10-day non-guaranteed contract. Miles then played the two games necessary to trigger re-addition of the $18 million to Portland's cap amount. Miles then re-signed two more 10-day contracts with the Grizzlies before being signed for the rest of the 2008–09 season on January 30, 2009.
Miles' final NBA game was played on April 13, 2009, in a 110–119 loss to the Phoenix Suns in which he recorded two points, two rebounds and an assist in six and one-half minutes of playing time.
