Jrue Holiday has had a resurgent season in Portland, justifying the Trail Blazers' offseason trade that took many by surprise. The talent was never in question. It had more to do with how Holiday fit Portland's rebuilding timeline.
Many expected Anfernee Simons to be moved as the Blazers double down on their defensive identity and proactively get ahead of his expiring contract. However, it was thought that they'd trade Simons for future assets, clearing the path for Scoot Henderson to take over the keys to the backcourt. General manager Joe Cronin had other plans, acquiring an aging and expensive star in Holiday.
Blazers' Jrue Holiday has worked out perfectly up until this point
Everything has gone to plan in terms of Cronin's vision for bringing Holiday into the equation. The Blazers' veteran guard has served as a bridge for their two-timeline approach, boosting their playoff chances in the short term while also improving their long-term outlook thanks to his veteran presence.
But what exactly is the next step in that plan?
The Blazers have made some contradictory moves when it comes to their timeline. They bring in Holiday as a win-now move while drafting a multi-year project in Yang Hansen the same summer. Eventually, Portland will be better off picking a lane, as it's difficult to straddle two timelines effectively. Just ask the Golden State Warriors how that's been going as of late.
Blazers need to commit to a timeline this summer
Damian Lillard's return adds another layer of complexity to Portland's decision-making. The front office could decide to accelerate the timeline around Holiday and Lillard's closing windows. However, the Blazers' roster still has quite a way to go before being considered a genuine contender and making that approach worthwhile.
They could simply stay the course and add Lillard to this roster, continuing their gradual improvement as a team destined for the playoffs next season. That's still likely a first-round exit in the stacked Western Conference.
The harsh reality is, Portland doesn't have quite enough pieces to show for its long rebuilding process. They haven't quite nailed the draft, as question marks surround Shaedon Sharpe, Scoot Henderson, and rookie Yang Hansen.
The Blazers have done a good job of compensating for that by winning their trades, stealing building blocks Deni Avdija and Toumani Camara. The downside is that it puts Portland in a strange position, as it is essentially in no-man's land. Too talented to join the long list of tanking teams this season, not talented enough to make a playoff run.
That's the worst position for a team to be in, and this offseason, they'd be wise to lean fully into one timeline or the other. What the Blazers decide to do with Holiday this summer will tell a lot about which lane they decide to pick. At this point, it could go either way.