The Portland Trail Blazers should be considered the wild card team to watch this offseason. They could follow up their successful 42-40 win season by taking this roster in a variety of different directions under Tom Dundon. Portland's new owner has a hands-on approach and will have his first summer to evaluate this organization from top to bottom.
However, this season has proven that Portland's roster doesn't need a significant shake-up. In many ways, they simply need to stay the course. Despite their series loss to the San Antonio Spurs, this was the first winning season in five years; that trajectory should only improve as their youth continues to develop, aligning with the anticipated return of their franchise icon, Damian Lillard.
1. Robert Williams III
Time Lord has proven his value in Portland, becoming fully healthy and arguably the best backup big man in the entire association. That's a double-edged sword, as now the risk of losing Williams in free agency is increased. Bill Simmons even predicted that Portland could lose Williams to a surprisingly lucrative deal, suggesting a team could sign him to a three-year, $50 million contract.
As good as Williams has been in Portland, they can't afford to keep an injury-prone center for that amount. Not when they recently invested consecutive first-round picks at the center position, especially seeing as none of the bigs on their roster can slide down to the power forward position.
The Blazers should explore options to keep Williams around, as he adds another dimension with his defensive versatility. But ultimately, it may not be up to them. This productive season has actually come at a bad time, as his value is the highest it's been in years.
2. Matisse Thybulle
The Blazers are in a similar situation with Thybulle. While Williams is labeled the injury-prone player, Thybulle has quietly struggled to see the court during his tenure with the Blazers as well. Thybulle has totaled 45 games played over the last two seasons, with one unfortunate injury after another.
Although Thybulle largely fell out of Tiago Splitter's rotation in their series with San Antonio, he was valuable for Portland down the stretch of the regular season, returning in time to contribute to their end-of-season playoff push. He provides that defensive versatility on the wing, similar to a Kris Murray or Sidy Cissoko, but has emerged as a much more reliable floor-spacing option.
Thybulle has transformed his career into that of a 3-and-D specialist, an invaluable player archetype in the modern NBA. Teams around the league have to be noticing the two-way impact he's had in Portland, which could also prove to be bad timing as he hits free agency.
Williams and Thybulle are the ideal veterans to keep around to align with Lillard's timeline and the closing window of their aging stars. Then again, just about every contender in the league should want these players' services.
If Thybulle ultimately walks, hopefully the Blazers can replace him with Murray and Cissoko. But that's easier said than done, with the Australian wing becoming an integral piece to this roster now that he's healthy.
3. Blake Wesley
This one stings, as Blake Wesley has become a fan favorite in Rip City. He immediately fit into general manager Joe Cronin's vision, picking up players the length of the court and absolutely hounding ballhandlers. Wesley's speed, defensive pressure, and unselfishness are exactly what the Blazers should be looking for in a role player.
Unfortunately, his foot fracture derailed some of that momentum. Portland's backcourt of Scoot Henderson, Shaedon Sharpe, and Jrue Holiday finally got healthy, making Wesley the odd man out. It's only going to get harder to crack that rotation with Lillard back in the picture next season.
As great a fit as Wesley is defensively, he's equally a liability on offense. Portland finished the season tied for third-worst in three-point efficiency, and keeping around a point guard shooting 27.8 percent isn't going to help address that glaring issue.
The Blazers must find a better balance at the end of their bench, as Murray, Cissoko, and Wesley all shrink the floor. Wesley may be the odd man out, considering the other two are under contract for next season. Not to mention, wings are far more valuable to keep around than guards, especially in a Blazers backcourt that suddenly has an ideal blend of youth and veteran stars.
Wesley was serviceable in Portland and even exceeded expectations at times, filling the void when their backcourt was depleted. That won't be the case next year, and it's become harder to justify keeping him around.
Hopefully, he's able to stick around in the league as Wesley is just 23 years old and a former first-round pick. But if the Blazers want to clear a spot this summer, his expiring contract should be the first to go.
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