From infamous draft blunders to heartbreaking playoff collapses, revisit the defining "what if" moments and missed opportunities that altered the course of this storied NBA franchise forever.
Every franchise has moments that change its future.
For the Trail Blazers, some of those moments became part of NBA history for the wrong reasons. Whether it was draft decisions, missed opportunities, or situations that completely altered the direction of the team, Portland has had several “what if” moments that still follow the franchise decades later.
Here are the five biggest mistakes in Blazers history.
Passing on Kevin Durant for Greg Oden
This one hurts for one reason.
Portland was not criticized heavily at the time for drafting Oden first overall in 2007. Many teams would have made the same choice because Oden looked like a franchise-changing center prospect.
The problem was health.
Oden’s career was devastated by injuries, while Durant became one of the greatest scorers in league history. What makes this especially painful for Portland fans is that the franchise already had another promising young core with Brandon Roy and LaMarcus Aldridge waiting to break through.
The Collapse Against the Lakers in 2000
The Blazers were minutes away from the NBA Finals.
Portland held a 15-point fourth-quarter lead over the Los Angeles Lakers in Game 7 of the Western Conference Finals before everything unraveled. The Lakers stormed back behind Shaquille O'Neal and Kobe Bryant, ending one of the most talented eras in Blazers history without a Finals appearance.
Many fans still believe that was Portland’s best chance at another championship.
Failing to Maximize the Brandon Roy Era
This one is complicated because injuries played a major role, but Portland never fully capitalized on the window it had.
Roy looked like a future superstar before knee injuries changed the trajectory of his career. Combined with Oden’s health issues, one of the league’s most promising young cores disappeared before it truly had a chance to peak.
For Blazers fans, it remains one of the biggest “what could have been” eras in NBA history.
The End of the Damian Lillard Era
The breakup between Portland and Damian Lillard will always be painful because of how much he meant to the franchise.
Lillard stayed loyal to Portland through multiple roster changes and playoff disappointments, but the organization never fully built a championship-level team around him. There were strong teams and memorable runs, but the Blazers never truly broke into contender status during his prime.
Watching one of the greatest players in franchise history leave without reaching the Finals felt like a missed opportunity for everyone involved.
Passing on Michael Jordan in 1984
This will always be the one people remember first.
Portland selected Sam Bowie with the No. 2 pick in the 1984 NBA Draft, one spot ahead of Jordan. At the time, the Blazers believed they needed a center more than another guard because they already had Clyde Drexler on the roster.
The logic may have made sense then, but the result became one of the most infamous draft decisions in sports history.
Jordan went on to become the greatest player ever, while injuries heavily impacted Bowie’s career. It is impossible not to wonder how different NBA history would look if Portland had paired Jordan with Drexler.