Worst free agency signings in NBA history: 17. Brandon Roy, Portland Trail Blazers
Brandon Roy was one of the more well-known names back in the day for the Portland Trail Blazers. Before his arrival, the Trail Blazers went 21-61. With his arrival in a draft-day trade in 2006, things changed for the better. Roy went on to win NBA Rookie of the Year, averaging 16.8 points, 4.4 rebounds, 4.0 assists and 1.2 steals per game.
After the 2008-09 NBA season, it looked like Roy and the Trail Blazers were on their way to greener pastures. Roy had just led Portland to a 54-28 record and an appearance in the NBA Playoffs with LaMarcus Aldridge in tow. He was due for a contract extension.
In August 2009, the extension came in the form of a five-year, $82 million deal from the Trail Blazers front office. They were reluctant at first, but in the end, Roy got his wish and proved to come through on his end of the bargain during the 2009-10 NBA season.
Roy put up 21.5 points, 4.7 assists and 4.4 rebounds per game for Portland. In the 2010 NBA playoffs though, he went down with a knee injury that would haunt him for the next year and then some.
He attempted to return in 2010-11, appearing in 47 games but due to his failing knees, he was forced to retire early at the age of 27. He tried to make a comeback with the Minnesota Timberwolves during the 2012-13 NBA season but after five games, he called it quits once again.