9. Brandon Roy stays healthy?
The Trail Blazers pulled off a clever move to get Roy to Portland in the 2006 draft, and he quickly took a star turn. The 6’6 wing won Rookie of the Year in 2007 before making three straight All-Star appearances. Roy should have just been entering his prime in 2011, but that turned into his last real season in the league.
He dealt with knee injuries throughout his early years, and the degenerative condition forced him to retire at 26. Roy came back for five games with the Timberwolves in 2012 before hanging up the sneakers for good. The 6’6 wing was an elite scorer and one of the best guards in the league, but he just could not stay healthy.
Portland won 11 more games in Roy’s rookie year before a nine-victory improvement in year two and adding 13 more wins in his third season. If he kept ascending, the sky was the limit. Brandon Roy could have been the best player on a title-contending team, but it was not meant to be.
He was an elite athlete with a strong jumper and the ability to get the rim at any moment. This is a heartbreaker for Portland Trail Blazers fans because the franchise never advanced beyond the first round of the playoffs with Roy, and there will always be wonder about what could have been.