The Portland Trail Blazers are eager to contend with Damian Lillard, but should the team think about hitting the reset button sooner than later?

The Portland Trail Blazers entered last season with a healthy Damian Lillard and title aspirations. Lillard did his part: 32.2 points, 4.8 rebounds, and 7.3 assists per game on .463/.371/.914 splits. By all measures a career year for one of the best point guards of his generation.

The result? 33-49, 13th place in the West, and the No. 3 overall pick in the 2023 NBA Draft. The Blazers have tried for 11 years now to build a contender around Dame. They've made it to the conference finals once in that span, which resulted in a four-game sweep at the hands of Golden State in 2019.

Lillard is 32 years old. His competitive window, his basketball prime, will not last forever. He has already dealt with the consequences of a severe, years-long core injury. Can the Blazers justify running it back?

That's the question the team will have to answer this summer. Lillard doesn't appear ready to demand a trade, but the front office is more than capable of making an executive decision and giving Lillard a hero's sendoff. Plenty of eager contenders will pay top dollar for a star of Lillard's caliber. Meanwhile, the Blazers have multiple young pieces to start their rebuild with — primarily Anfernee Simons, Shaedon Sharpe, and the upcoming No. 3 pick.

If Portland decides to keep Lillard and make one more stab at glory, how exactly does that happen? Are any free agents of note interested in joining the Blazers' perennial parade of disappointment? Can the Blazers swing a needle-moving trade without completely gutting their future?

Regardless of which direction the franchise takes, the road ahead is long and difficult. Rebuilds aren't easy. Neither is pulling a team out of the NBA basement and putting it on the mountaintop. This summer will be pivotal to determining the legacy of this Blazers team and the direction of the franchise moving forward.

Portland Trail Blazers outgoing free agents

No matter which direction the Blazers go, their free agency decisions will be of paramount importance. Here are the team's current outgoing free agents:

• Jerami Grant, 29, F
• Cam Reddish, 23, F (RFA)
• Justise Winslow, 27, F
• Matisse Thybulle, 26, F (RFA)
• Kevin Knox, 23, F (Club Option)
• Drew Eubanks, 26, C
• John Butler, 20, C (RFA)
• Ibou Badji, 20, C (RFA)

The biggest name here is Jerami Grant, who has emerged as one of the NBA's best tertiary stars. He covers a ton of ground defensively and is one of the best answers to elite wing scorers in the NBA. On the offensive end, Grant is a reliable spot-up shooter and dynamic slasher who thrived attacking the seams in the defense created by Lillard's shooting gravity last season.

Grant will demand a significant contract on the open market. Most of the teams with cap space are rebuilding, but teams like Houston or San Antonio could be willing to overpay for veterans in order to take the next step. This will be a potential inflection point for Portland. If the team re-signs Grant, that probably means at least one more year with Lillard helming a theoretical contender. If Grant walks, then maybe the reset button has already been pushed.

The restricted free agents will also be interesting to watch. Portland traded for Cam Reddish and Matisse Thybulle at the deadline and immediately handed them big roles. Reddish is 23 and still has room to grow. Thybulle is more or less a known quantity — gobsmacking on defense, but a major thorn in the offense's side.

How much money do they fetch on the open market? What is Portland's competition like? The Blazers can match any offer, and likely will within reason, but overpaying for Reddish or Thybulle wouldn't do them any favors in the short or long term.

Drew Eubanks was the best center on the roster last season. The Blazers could look to address that problem in free agency or the draft, but Eubanks shouldn't be particularly expensive to keep around.

Portland Trail Blazers trade targets

The Blazers will absolutely scour the market for foundation-shifting trades. Whether any such move is possible or practical is another matter entirely.

There has been a lot of buzz around dangling the No. 3 pick in trade conversations. If Scoot Henderson does eventually fall into Portland's lap, there should be a line of interested suitors around the block. That being said, how many 'star' players are available for the No. 3 pick that are actually worth it? Henderson is a potential bridge to the future for Portland; swapping him for, like, OG Anunoby would be a crippling example of shortsightedness.

Pascal Siakam and Jaylen Brown are the potential heavy-hitters to watch. Either would elevate Portland's standing in the West enough to justify a move, especially Brown, who's only 26 years old. But neither feels particularly likely, and even then the Blazers should still strongly consider just riding with Scoot.

If the offseason veers in the opposite direction, Portland could consider trading Lillard. That would net them a significant stash of young talent and draft capital to further their rebuild. The Knicks, Heat, Nets, and Celtics feel like the primary candidates there. The Celtics are more likely to listen to Jaylen Brown trade offers if Lillard is involved.

Other possibilities to consider: a Jerami Grant sign-and-trade. If Grant wants to join a winner, he probably won't find one with enough money to sign him outright. The best bet would be to orchestrate a sign-and-trade with Portland, which could net the Blazers another asset or two.

Also, Anferee Simons is a sneaky trade candidate if Scoot Henderson is the pick at No. 3. Both Henderson and Lillard are 6-foot-2, traditionally ball-dominant point guards. Simons would feel like the odd man out as a 6-foot-3 guard who deserves the ball too. He's young and quite good — the Blazers could get a lot for him.

Portland Trail Blazers free agent targets

The Blazers will not have much cap space this summer. The primary focus will be on outgoing free agents (yay or nay on Grant, keeping the young wings). Portland could chase mid-level free agents like Dillon Brooks or Malik Beasley, but even that gets tricky.

Portland should, however, search the bargain bin for quality center options. Jusuf Nurkic has lost more than a step and while there are minutes to be shared between Drew Eubanks and Trendon Watford, Portland would be wise to target more experienced rim protectors if the goal is to build a winner around Lillard.

Portland Trail Blazers NBA Draft targets

The Blazers own the No. 3, No. 23, and No. 43 picks in the NBA Draft. The options at No. 3 appear simple on the surface: either Scoot Henderson or Brandon Miller, depending on who Charlotte lets slide past No. 2. That said, Portland is also expected to consider Amen and Ausar Thompson, who recently worked out for the team. Both are much cleaner positional fits on defense than Henderson if the goal is to build around Lillard.

At No. 23, Portland would be wise to hammer the center market: Duke's Dereck Lively II if he's there, Barcelona's James Nnaji or Alabama's Noah Clowney if he's not.

For more information on this year's NBA Draft class, check out our latest Mock Draft and Big Board.

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