8. Brandon Roy
For most NBA fans, Brandon Roy is remembered as one of the biggest “what-if” stories in league history. Drafted by the Portland Trail Blazers in 2006, he quickly came on the scene as one of the most exciting young players in basketball, winning Rookie of the Year in 2006-07.
From there, Roy continued to elevate and earned his first All-Star selection in his second season, which was shortly followed by his first All-NBA nod the following season. He would go on to be named to All-NBA and All-Star teams in 2009-10 as well.
Unfortunately, Roy had a history of knee problems, and just as he was emerging as one of the best guards in the league, his knees began giving him trouble once again. Roy’s 2010-11 season was ended due to undergoing arthroscopic surgery on both of his knees. Before the following season began, Roy announced his retirement due to ongoing knee problems.
It was widely believed that he would never step foot on the court again, but in the summer of 2012, Roy announced he would attempt to make an NBA comeback. The Minnesota Timberwolves ended up signing him to a two-year, $10.4 million contract. Roy would appear in five regular season games for the Wolves, before once again needing knee surgery that would ultimately force him into retirement a second time.
It was a low-risk, high reward situation for the Timberwolves, which is why this signing ranks lower on our list. There is no doubt most NBA fans were rooting for Brandon Roy’s success after his unfortunate injury luck, but the Wolves’ reclamation project with him was ultimately a failure.