When they are ready to make that next jump, you could make a case that the Portland Trail Blazers' young core is better equipped to succeed in the postseason than what Damian Lillard had to work with. They are establishing more of a defensive-minded team that is long and athletic, which should translate well to the playoffs when teams become more physical and intensity picks up.
Lillard was incredible in Portland and is arguably the best to ever put on a Blazers jersey, but the Blazers failed to put the necessary pieces around him. They continually added and kept players that helped maintain competitiveness but weren't going to be the needle movers to help put Portland into true contention.
In retrospect, the Blazers should have embraced a full-on teardown to rebuild around Lillard in 2015 following LaMarcus Aldridge's departure to San Antonio.
They were heading that way when they dealt Nicolas Batum to Charlotte for Noah Vonleh and Gerald Henderson (horrible trade, but the right idea). But then they contradicted their direction, trading first-round pick Rondae Hollis-Jefferson to Brooklyn for Mason Plumlee and Pat Connaughton. Those additions helped Portland finish with a 44-38 record the following year, where they exceeded expectations.
There's some terrifying overlap between that 2015-16 season and the surprising season the Blazers are finishing up.
Blazers must avoid long-term purgatory
Sean Highkin of Rose Garden Report covered Joe Cronin's recent extension, writing that the Blazers are committing to Cronin's vision with major franchise decisions looming. Highkin notes that Cronin's next challenge outside of determining who next year's head coach will be is overcoming a similar obstacle that hindered the Blazers throughout the Lillard era: long-term purgatory.
"Recognizing that tanking for another high lottery pick is no longer realistic with this group improving as much as it did this year, and making roster upgrades to further that growth and push towards the playoffs, but not going so far in that direction that it boxes them into the exact kind of long-term purgatory they were in for most of Lillard’s prime," wrote Highkin.
This season, the Blazers are in "no man's land" as a team that is out of play-in contention but has minimal odds of landing a top pick. They need to move on from their veterans, but even if they do, their young core has become too talented to land a top pick again. That forces the Blazers to start building their roster in the other direction as a team that wants to compete for a playoff spot sooner rather than later.
The fans deserve that after enduring years of tanking -- even during the final stretch of the Lillard era, when they shut him down only to draft his eventual successor in Scoot Henderson. But, as Highkin notes, it's a balancing act.
The Blazers' long-term goal isn't just to make the playoffs -- it's to win it all. With Lillard, they seem to have lost sight of that, making moves to keep them afloat but never to push them over the top. If there is overlap between 2015-16 and 2024-25, the Blazers need to learn from their mistakes.
The 2016 offseason was where things fell apart. Portland locked itself into long-term purgatory, matching a four-year, $75 million offer sheet to retain Allen Crabbe and signing Evan Turner to a four-year, $70 million deal. Those are the exact type of decisions the Blazers need to avoid this time around.
They hit on their trades for Toumani Camara and Deni Avdija, but Cronin's tendency to value players over draft picks is a risky proposition that might backfire down the road. The one thing he does well is make sure that these players fit into the timeline of their young core. That's exactly what the Blazers don't want to do -- acquire someone like 29-year-old Cam Johnson for valuable draft capital to make a win-now move with no realistic shot of winning it all.
But at some point, the Blazers will have to be more aggresive to get out of this "no man's land" they find themselves in. That's when we'll know whether Cronin's extension was truly in Portland's best interest.