Today, he is set to make a comeback.
As one of the premier shooting guards in the league, the former Rookie of the Year and three time All-Star is an unrestricted free agent after missing the entire 2011-12 season.
Five teams have already expressed interest in signing the 27-year-old and his addition to any team would be a welcome one.
Chicago, Golden State, Minnesota, Indiana and Dallas are all reportedly in pursuit of Roy, a player that has continued to exceed expectations throughout his career.
Health concerns as he was coming out of Washington led to him slipping in to sixth overall in the 2006 NBA Draft.
Portland acquired Roy during a draft day deal that sent Randy Foye to Minnesota and saw him become a star.
As a rookie he averaged 16.8 points, 4.4 rebounds and four assists per game, the point and assist totals were the highest averages of any player in his class, as he secured 127 of 128 first place votes for Rookie of the Year.
The next season he was selected as an All-Star for the first time in his career and he scored 18 points on 8-of-10 shooting along with nine rebounds, a block and a steal.
Although he is listed as a shooting guard, Roy was essentially the point guard for Portland, leading the team in total assists for consecutive seasons while serving as the primary ball-handler.
Equally adept at setting up teammates or creating his own jump shot, Roy’s breakout season came in 2008-09 as Portland won 54 games.
Roy averaged 22.6 points and 5.1 assists per game even though the Trail Blazers played at the slowest pace in the NBA and the team pushed LaMarcus Aldridge into a primary offensive role.
The transition towards Aldridge becoming the franchise player was a necessity, after doctors declared Roy had no meniscus left in his knees.
In his final season with Portland, Roy was only able to appear in 47 games, starting just 23 and averaging a career-low 27.9 minutes per game as continual knee problems forced him to the sideline.
During his final season in Portland, surgery was required for Roy as 2010 the playoffs were about to begin.
Eight days after undergoing the procedure, Roy returned to the court for Game 4 against Dallas as the theme to Rocky blared from the Rose Garden sound system.
The comeback was just starting on that Saturday afternoon.
Roy scored 18 fourth quarter points, leading the Trail Blazers back from an 18-point deficit in the quarter to tie the series.
Although Portland fell to the eventual champion Mavericks, Roy once again displayed his ability to take over when necessary.
Three of the teams interested in Roy are hoping he can provide some offensive contributions as their stars recover from injury.
After dealing him away six years ago, Minnesota is set to offer Roy a two-year contract, even with his knees still in question.
The addition of Roy would be a perfect filler for the Timberwolves, as he can temporarily play point guard as Ricky Rubio recovers from his own knee surgery.
The combination of Roy and Kevin Love would give the team two dynamic scorers and may be enough to lead Minnesota into the post season for the first time since 2004.
Chicago has finished with the top record in the Eastern Conference each of the past two seasons but will be without Derrick Rose as he recovers from a torn ACL injury suffered against Philadelphia in the playoffs.
The Bulls selected Marquis Teague with their first round pick but the addition of Roy would provide much needed upgrade at shooting guard.
Golden State is hoping Stephen Curry can fully recover from his series of ankle injuries that limited him to just 26 games last season.
Sunday marked the first day teams could pursue free agents and following a year away from the game, Roy would be a welcome addition to any NBA franchise.
Roy could provide some guidance for the sharpshooting Klay Thompson.