Now it looks like one of the once-promising rising stars will see his career come to an unfortunate end.
On Friday, the Minnesota Timberwolves waived Roy after one season. The former three-time All-Star played just five games for the Timberwolves, missing significant time due to severe knee injuries that forced the Blazers to amnesty him before the 2011-12 season.
Roy may not have helped the Blazers to a playoff series victory. You won't see his name among the all-time statistical leaders in franchise history. But the memories he provided fans have become legendary for those who witnessed his time in Portland.
Roy, who was the 2007 Rookie of the Year, meant much more to Blazers fans than simply as a player.
The Seattle native and University of Washington product represented the transition from the forgettable Jail Blazer era during the mid-2000s to a revival of Rip City. Roy's clutch plays to finish ballgames became a norm at the Rose Garden. With the ball in his hands, you were confident in his ability to do the right thing and will the Blazers to victory.
In 2009, the Blazers at last made the playoffs in Roy's third season for the first time since 2003.
Roy had the best season of his career, finishing ninth in the NBA MVP voting, was voted an NBA All-Star for the second time and was named to the All-NBA second team—the first Blazer to make an All-NBA team since Clyde Drexler in 1992.
With a core of Roy, LaMarcus Aldridge and former No. 1 pick Greg Oden, the question was not if Portland was going to win an NBA championship, but when and how many?
The Blazers went 54-28 in 2008-09 with Roy, Aldridge and Oden in their early 20s. They were considered the future of the NBA—what the Oklahoma City Thunder have become today.
While Oden received much of the fanfare as a potential once-in-a-generation center, the Blazers were unquestionably Roy's team. He was their go-to guy down the stretch.
Roy holds the Rose Garden record for most points in a game with 52 on Dec. 18, 2008 in a nationally televised game against the Phoenix Suns. TNT analyst Mike Fratello said during the telecast that Roy took "his game to new level" that night as fans serenaded him with "MVP" chants late in the game.
"This is the best game I've played," Roy told The Oregonian. "I've never scored (that many), even in little league."
Let's also not forget the biggest dunk by far of his career when he posterized the Los Angeles Clippers' Chiekh Samb at Staples Center.
Fans were ready to hoist Roy's No. 7 jersey up in the rafters. He was on his way to displacing Drexler and Bill Walton as the best player to ever wear a Blazer uniform.
Entering the 2010-11 season, however, it was apparent after countless knee surgeries that Roy was not going to be the same player. His degenerative knees that had no cartilage had a huge impact on his game, which suddenly was missing the explosiveness and athleticism that made him such a special player.
He started the final game of his career in a Blazer uniform on Dec. 15, 2010 where he totaled four points, two rebounds and five assists in a 103-98 loss to Dallas.
He did not return to the lineup until Feb. 23, 2011, where he turned into a permanent reserve. His final lasting memory among Blazers fans became a truly remarkable performance in Game 4 against the Dallas Mavericks in the first round of the 2011 NBA playoffs.
He helped engineer a 23-point second-half rally by scoring a game-high 24 points in one of the greatest comebacks in NBA history. The Blazers won, 84-82.
Portland eventually lost the series 4-2 to the Mavs, who went on to win the NBA title. But that Game 4 was etched into the minds of Blazers fans as one of the most memorable in franchise history. It seemed fitting that Roy would give one last Roy-like performance to remind the home crowd of the player he was.
Portland decided to amnesty him in the ensuing offseason just one year into a five-year, $82 million contract, which led to his unexpected retirement (h/t Joe Freeman of The Oregonian). It was a big blow to not only Portland, but around the NBA as players reacted on Twitter at the time.
LeBron James @KingJames
Please say it ain't so. Brandon Roy retiring. Losing one of the best 2 guards in the league before he's ready to go. So unfortunate man! SMH12/9/2011, 4:25:33 PM
Carmelo Anthony @carmeloanthony
Not Brandon Roy!!!!!!!! The #NBA is losing a great one. Damn!!!!!!!!!12/9/2011, 4:47:15 PM
Jason Richardson @jrich23
Man hate to see a player like Brandon Roy retiring. Was such a great player wish him nothing but the best.12/9/2011, 6:13:48 PM
Mario Chalmers @mchalmers15
Crazy to hear bout B Roy. One of my good friends and somebody I always looked up too and respected. The game will miss u bra12/9/2011, 4:36:33 PM
Then-Blazers coach Nate McMillan said it was a tough time to release a player who had been the face of the franchise's turnaround (via Jason Quick of The Oregonian):
The Closer has closed. He was a guy who in the last few years was one of the best closers in the league. When Brandon had the ball in his hands late in ball games, I was really comfortable. You knew something good was going to happen. He was either going to create a shot for himself, or a shot for his teammate. He had some big moments in a short career.
Roy had two opportunities to make his comeback to the RG this past season as a member of the Wolves, but his knees forced him to sit both times. He addressed his return to Portland in March when Minnesota visited and said, "It would have been special for me to come back and play here in this building."
After the Blazers used their amnesty clause, they left the door open for Roy to return in some way down the road should he desire to come back.
Jason Quick @jwquick
Blazers owner Paul Allen met with Brandon Roy yesterday and gave open invitation for Roy to join the org. in some capacity down the road12/16/2011, 12:20:19 AM
His nickname was "The Natural," given to him by radio play-by-play announcer Brian Wheeler. No nickname better suited his game. If healthy, Roy would just be entering his prime today at 28 years old.
His departure from Portland not only was a punch to the gut to fans, but Roy admitted it was difficult for himself (h/t Jason Quick of The Oregonian).
You can walk away from someone who doesn't love you. And you can walk away from someone you don't love. But when the love is mutual, the hardest thing is to walk away.
It's a shame to see a career likely end too early, but Blazers fans who saw Roy play from 2006 to 2011 will no doubt look back on the memories and say, "I was definitely privileged to have witnessed Brandon Roy play."