From the loaded 2000 roster to Damian Lillard’s magical 2019 run, rediscover the legendary squads that dominated the court but fell just short of a championship series.
The Portland Trail Blazers have had multiple teams come painfully close to the NBA Finals without ever finishing the job, but two groups stand above the rest when this conversation comes up.
The 1999-2000 team and the 2018-19 team.
One came within minutes of reaching the Finals before collapsing against the Lakers in Game 7 of the Western Conference Finals. The other rode a magical playoff run behind Damian Lillard all the way to the Western Conference Finals before running into the dynasty-era Warriors.
Both are remembered fondly in Portland.
But which team was actually better?
The 2000 team probably has the stronger overall case.
That roster was loaded with experience, depth, and physicality. Portland won 59 games and had one of the deepest teams in the league with players like Scottie Pippen, Rasheed Wallace, Steve Smith, Arvydas Sabonis, and Detlef Schrempf. They were tough defensively, versatile offensively, and built specifically for playoff basketball.
And for most of Game 7 against the Lakers, they looked like the better team.
Portland famously held a double-digit fourth-quarter lead before everything unraveled late. The collapse remains one of the most painful moments in franchise history because the Finals felt within reach. Many Blazers fans still believe that team was talented enough to win a championship if it had closed that game out.
The 2019 team had a very different identity.
That group was built around Lillard and CJ McCollum, with role players stepping up during an emotional playoff run. Portland knocked off Oklahoma City in memorable fashion, including Lillard’s iconic series-ending shot, before beating Denver in a seven-game battle to reach the conference finals.
The run felt special because of the circumstances.
Few expected that roster to make it that far, especially with injuries limiting key contributors. The team played with confidence, toughness, and chemistry, and for many fans, that playoff run became one of the defining moments of the Lillard era.
But compared to the 2000 roster, the overall talent gap is hard to ignore.
The 2000 team had more depth, more size, more defensive versatility, and a more complete roster from top to bottom. The 2019 team had heart and momentum, but the 2000 group looked much closer to an actual championship-caliber team.
That is what makes the debate interesting.
One team may have been more beloved.
The other may have been the best team Portland never saw in the Finals.