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The Biggest Trail Blazers “What If’s” Ranked

A reader wants to know what team losses were the toughest in Blazers franchise history.

1990 NBA Finals Game 4: Detroit Pistons vs. Portland Trail Blazers Photo by Andrew D. Bernstein/NBAE via Getty Images

It’s Christmas weekend, Portland Trail Blazers fans! Amid our other posts, we’re going to throw in some free stocking stuffers: mini-Mailbags with questions that require only a short response! Think of them as snack-sized versions of your usual Blazer’s Edge Mailbag.

Since I love the history questions, I’m happy Bryan wrote in with a question about “What Ifs”!


I’m curious what you think about ranking the Blazers biggest what if moments. I don’t mean players like Bowie instead of MJ. With teams, one of my personal what ifs is the 2014-15 team when Wes Matthews ruptured his achilles tendon. If that didn’t happen they were contenders for sure. That might be my biggest one but where does it rank for you?


It makes the list, but it’s farther down for me. Even with Matthews, I’m not sure that team makes a serious title run. The playoffs kerthunk against Memphis made it feel way worse, but I don’t think it was even close to the most agonizing. Here’s my list.

1990-91 Western Conference Finals Loss to the Lakers

Objectively this should be in a tie with, or maybe below, the next event on the list, but it’s my personal hell. The Blazers had a franchise-record 63 wins in ‘90-’91. They had just gotten Cliff Robinson and Danny Ainge acclimated off the bench, adding serious depth to the familiar starting five of Drexler, Porter, Kersey, Williams, and Duckworth. They were coming off an NBA Finals appearance, firing on all cylinders, with a single goal: the championship.

They cruised through the regular season, meeting an aging Lakers team in the Conference Finals. They were expected to win, but they dropped Game 1, then had to scramble back in a decisive Game 6 in which they almost took L.A., but fell one shot short. I sat after the game in stunned disbelief. If that shot had fallen. If they had been able to force Game 7. The Lakers put up no fight against the eventual champion Chicago Bulls, who also had 63 wins. That was Michael Jordan’s first ring. It could have been Clyde’s. Arrrrgh.

1978 Second Round Loss to the Sonics

Portland famously won the 1977 NBA Title and, with a 58-24 record, were well on their way to repeating the feat when Bill Walton went down. The NBA playoffs were structured to give the first seed in each conference a bye into the second round in those days. Portland’s dethroning was staved off for a week, but they ultimately fell to the Seattle Supersonics, who would advance to the NBA Finals themselves against the Washington Bullets, then win it all a year later. If Walton had stayed healthy, neither might have happened. Portland could have repeated or three-peated in an era where that just didn’t happen.

1992 NBA Finals Loss to the Bulls

The Blazers would get another crack at the Bulls in 1992, riding the back of Clyde Drexler, who personally willed his team to another successful run. It fell short 4-2 in the ultimate series, but the Blazers coughed up a big lead in the final game. What if they had held it and forced a Game 7? They had not been so close to a Finals victory since ‘77 and they’ve never been that close again.

1990 NBA Finals Loss to the Pistons

The painful 1-4 loss to the Detroit Pistons in the 1990 NBA Finals gets pushed down the list because this was Portland’s first trip to the big show in this incarnation and they were still finding their way. They stole homecourt advantage in Detroit, but couldn’t back it up, losing three straight at home. But who could forget the marvelous feeling after the Game 2 win, or Danny Young’s halfcourt buzzer-beater at the close of Game 4 that was waved off as slightly too late? (sigh) What if that shot had counted?

2000 Conference Finals Loss to the Lakers

This was the famous Fourth Quarter Collapse that needs no rehearsal for anyone who lived through it. Many Blazers fans would rank this higher, some even highest, on the list. I don’t because the team got down huge in the series to begin with and was lucky to make it to Game 7. Also that incarnation of the Blazers was only semi-likeable. Plus the league had kind of a fix in during these years, allowing Shaquille O’Neal to do whatever he wanted, and no amount of “What If”-ing could overcome Papa Stern and the marquee-obsessed NBA. Still, had the Blazers finished out the final minutes of Game 7, the Indiana Pacers were ripe for the picking and Portland probably would have won their second title.

Nurkic Breaks His Leg in 2019

The Blazers were playing their prettiest basketball since 2000 during the 2018-19 season. Jusuf Nurkic was a key part of their scheme, playing the best basketball of his career on both ends. You know the story. He fractured his leg coming down from a rebound against the Brooklyn Nets and spent the next year and a half on the shelf. Portland still made it to the Conference Finals before getting ousted by a wounded Golden State Warriors team. Nurkic probably wouldn’t have saved that series, but it would have been far more fun to see the team at full strength through the end of the season.

Wes Matthews Drops in 2015

So here’s your Wesley Matthews moment. The Blazers were cruising, looking for a deep playoffs run behind Damian Lillard, Matthews, Nicolas Batum, LaMarcus Aldridge, and Robin Lopez. One blown tendon later and Matthews was out, leaving a huge void in the backcourt. Portland traded away Will Barton and a first-round pick for Arron Afflalo, but they were out of the playoffs after five games and Afflalo didn’t stick around.

Maybe you all disagree with my ordering? Or did I leave out one of your moments? If so, fill in below! And don’t forget you can send your own questions to