The NBA is built on the legends who sustain greatness over decades, but just as often, players exit the league long before fans are ready to let go.

Injuries, personal battles, shifting priorities, or tragedies have cut short careers that once seemed destined for historic heights.

With Ben Simmons reportedly questioning whether he wants to continue playing, it's worth revisiting some notable cases of players who left the game too early

22. Brandon Roy

Brandon Roy's story is one of the most painful “what ifs” in recent NBA memory. Drafted sixth overall in 2006 and quickly earning Rookie of the Year, Roy was everything Portland needed to rebuild its image after the ‘Jail Blazers' era. Nicknamed “The Natural,” he was a fan favourite in Portland and earned three All-Star selections within his first four seasons.

But beneath the highlights, his knees were deteriorating. Roy had no cartilage left between the bones, and despite surgeries and countless rehabs, the pain never went away. By 2011, at just 27 years old, he announced his retirement. This decision stunned teammates and fans alike. It was heartbreaking not only because Roy still had the talent to carry Portland, but because he embodied the franchise's return to credibility and competitiveness.

In his short career, Roy averaged nearly 20 points per game and gave fans unforgettable moments, like his 18-point fourth quarter to lead a 23-point playoff comeback against Dallas in 2011. Roy's career ended far too soon, but the impact he had on Portland and the respect he earned around the league remain untouchable.