May 25, 2026 12:00 PM
From Clyde Drexler’s 1992 finals run to the star-studded 2000 roster’s heartbreaking collapse, relive the legendary seasons that defined Rip City basketball despite missing the ultimate prize.
The Portland Trail Blazers have only won one NBA title in franchise history, but several teams came close to adding another banner. Some made the Finals, others fell just short, and a few still live in the minds of fans because of what could have been.
When the discussion turns to the greatest Portland team that never won a championship, two teams separate themselves from the rest.
The first are the 1991-92 Blazers and are followed by the 1999-2000 Blazers.
Both had championship-level talent. Both reached the edge of the NBA Finals stage. And both left fans wondering what could have happened if a few moments had gone differently.
So which team gets the top spot?
The case for the 1992 team starts with their accomplishments.
Led by Clyde Drexler, Portland finished the regular season with 57 wins and reached the NBA Finals after winning the Western Conference. That roster had depth, experience, and balance with players like Terry Porter, Jerome Kersey, and Kevin Duckworth playing major roles.
The Blazers were not simply good, they were one of the league's elite teams.
Drexler finished second in MVP voting and looked like one of the best players in basketball that season. Portland played with pace, toughness, and confidence, and they eventually reached the Finals before running into Michael Jordan and the Chicago Bulls.
Unfortunately for Portland, many teams from that era had the same problem.
Then there is the 2000 team.
For many fans, this remains the most talented Blazers roster ever assembled.
Portland won 59 games and was loaded with experience and depth. Scottie Pippen, Rasheed Wallace, Steve Smith, Arvydas Sabonis, and Detlef Schrempf gave Portland one of the deepest teams in the league.
And unlike the 1992 team, many still believe the 2000 team was minutes away from winning it all.
The Blazers famously held a 15-point fourth-quarter lead against the Los Angeles Lakers in Game 7 of the Western Conference Finals before the collapse that still hurts Portland fans today.
That is what makes this difficult.
The 1992 team accomplished more by reaching the Finals.
But the 2000 team may have been better.
The roster was deeper, more versatile, and arguably more complete from top to bottom.
If the question is greatest season, 1992 has a strong case.
If the question is greatest team, the answer may be 2000.
And that debate probably is not ending anytime soon.
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