Tony Allen (2004-10)
As a late first-round pick during the 2004 NBA Draft, Tony Allen became a contributing part of the Boston Celtics’ success during the 2000s. He also played a role for the team during the C’s Big 3 championship in 2008. Allen statistically had his best season in 2006-07. He only played 33 games that year but would go on to average 12 points and four rebounds on 51 percent shooting from the field.
However, after that 2007 season, Allen would continue to struggle with consistency and injuries with the Celtics. Still a strong defender, he’s probably a player that the Celtics could’ve decided to move on from sooner. After winning the championship in 2008, the Celtics re-signed Allen to a two-year deal. Though, he would miss roughly 30 games in each of the next two seasons.
Boston would go on to lose in the second round of the playoffs to the Orlando Magic in 2009 and then in the NBA Finals to the Los Angeles Lakers in 2010.
Looking back, you could make the argument that the Celtics and Allen should’ve parted ways after winning the championship. Allen would play out the next two seasons with the Celtics and then signed with the Memphis Grizzlies via free agency during the summer of 2010.