The Portland Trail Blazers are expected to pursue a star-level return for Damain Lillard — perhaps with the goal of staying in contention. Who can they realistically acquire?

Damian Lillard's trade request was awkwardly timed, if not particularly surprising. The Blazers have plenty of young players to anchor their rebuild, starting with No. 3 pick Scoot Henderson. But, Portland also agreed to terms with Jerami Grant on a new five-year, $160 million contract.

So, what is the path forward? Is it a simple rebuild with Grant putting up numbers and chaperoning the locker room, or does Portland want to keep their hat in the ring post-Lillard?

Joe Cronin and the Blazers' front office are expected to scour the league for the best available return. There could be mild trepidation tied to Lillard's age, injury history, and contract length, but he's a top-15 player who should return a significant asset haul.

If Portland wants to keep winning games — and frankly, Henderson will probably be good enough to lead a winning team sooner than later — here are five players the Blazers could realistically target in a Lillard deal.

No. 5 player Blazers could acquire in Lillard trade: Tobias Harris

Not the most exciting name, but Tobias Harris is a productive complementary "star" who can scale up to fill a bigger scoring role when asked to. He was once the best player on a Clippers team that made the playoffs, and Portland probably wouldn't complain about 20 points per game with Harris' trademark efficiency.

The fit between Harris and Grant in the frontcourt is slightly unbalanced, but Harris has made significant strides on the defensive end in recent years. He's comfortable checking volume scorers on the wing and Grant is more than capable of locking up smaller players, so the defense shouldn't end up being too grave a concern.

On the offensive end, Harris is at his best when empowered to shoot spot-up 3s and make quick decisions with the ball. He has a bad tendency to record-scratch on the catch and he can over-dribble when asked to create, but the Blazers would surround him with multiple high-level playmakers and another self-creating forward in Grant. Ideally, Harris wouldn't be burdened with too much responsibility.

He would be part of a much larger package, of course, and Harris is only on the books for one more season. The lack of long-term commitment (at least at his current price point) should be viewed favorably by the Blazers, who will want the flexibility to pivot elsewhere post-Lillard.

No. 4 player Blazers acquire in Lillard trade: Walker Kessler

The Jazz would surely prefer to keep Walker Kessler, but we're talking about Damian Lillard. If Utah really wants to make a push for Lillard, it could come at the cost of Utah's best young player. And yes, even though Kessler is fresh off his rookie season, he would absolutely help the Blazers win games next year.

Kessler finished third in Rookie of the Year voting, which honestly doesn't reflect how impressive he was as the heir to Rudy Gobert in Utah. Kessler's defensive analytics were off the charts and he averaged 2.3 blocks in only 23.0 minutes per game. He's already one of the most prolific rim protectors in the NBA.

The Blazers' defense was in a world of hurt last season as Jusuf Nurkic's sharp decline infected the frontcourt. Replacing the aging Nurkic with Kessler — not to mention Grant's length and versatility on the wing and Scoot Henderson's ferocious on-ball guard defense — could transform Portland very quickly into an above-average defense.

Kessler doesn't just block shots either. He shot 72 percent from the field and dominated on finishes at the rim. His size, vertical threat, and soft touch make him a deadly scorer in the restricted area. He doesn't stretch the floor yet, but Kessler is a paragon of two-way efficiency and he's a good passer for his position too, so there's untapped offensive upside in a bigger role.

No. 3 player Blazers could acquire in Lillard trade: Jalen Brunson

The Knicks are well-documented star hunters. Damian Lillard has been front of mind for New York fans for years now, and here's their chance to finally get in on the action. Much has been made of Lillard's wonky fit next to Jalen Brunson in a hypothetical backcourt, but what if Brunson is the foundation of the trade package?

New York fans very quickly learned to love Brunson, so this move would come with understandable backlash. Brunson is six years younger than Lillard and he's primed for multiple All-Star appearances before his Knicks tenure is over. But, as good as Brunson was during the playoffs, there's an oceanic gap between Brunson and Lillard on the star spectrum. If the Knicks truly want to make the best pitch for Lillard, it might have to involve Brunson.

The Blazers would obviously have their own concerns about Brunson's fit in a backcourt that already includes Scoot Henderson and Anfernee Simons, but Portland would be wise to bet on talent over fit at this stage. Brunson was the best player on a second-round team last season, he's worth the investment.

Brunson and Henderson should be able to share the floor. Simons too, for that matter. Portland might have to swing a separate trade involving Simons to balance the roster at some point, but Brunson's unique pace and playmaking eye would be a fascinating counterweight to Henderson's explosive downhill slashing. Portland would be able to mix and match speeds and styles offensively while possessing multiple advantage-creators in the backcourt — it's a fun concept.

No. 2 player Blazers could acquire in Lillard trade: Jaylen Brown

Jaylen Brown's reputation took a definite hit in the Eastern Conference Finals — especially in Game 7, the game in which Brown committed eight turnovers and five fouls while scoring 19 points on 8-of-23 shooting. The game and the broader overall series led many to question the long-term viability of Brown as Jayson Tatum's co-star in Boston.

The Celtics are predictably not overreacting. Brown made second-team All-NBA last season and he remains an undeniably good player. He averaged 26.9 points and 6.9 rebounds on .491/.335/.765 splits for the second-best team in the NBA record-wise. He is flawed, yes, but there is absolutely a path to Brown as a cornerstone piece on a winning team.

Boston has not been mentioned in the early flurry of reporting around Lillard, but the Celtics have been unafraid to get involved in splashy trades before. Lillard is a short-term upgrade over Brown and a better fit for what Boston requires offensively. His pull-up shooting and playmaking ability would mesh beautifully with Tatum as the Celtics' one-two punch.

If the Celtics decide to push all their chips in, the Blazers would be happy to build the next chapter of Portland basketball around Brown. He'd be well-positioned next to Scoot Henderson, a high-volume playmaker who can put pressure on the rim and empower Brown to focus on his strengths: catch-and-shoot 3s, vicious downhill attacks, and secondary actions. Boston always ran into trouble when Brown was asked to self-create on a regular basis. With Henderson and Simons in the Portland backcourt, that wouldn't be as much of an issue.

No. 1 player Blazers could acquire in Lillard trade: Paul George

The Clippers are trying to pair James Harden with Kawhi Leonard and Paul George to form the league's next high-profile 'Big 3.' If Los Angeles were to pivot toward Lillard, however, it may be harder to formulate a respectable package without sacrificing one of the franchise's two cornerstones.

George is the obvious trade candidate in that event, even if he's slightly more dependable on the health and availability front than Leonard. The Clippers would hope to blend Leonard's deadly isolation scoring with Lillard's prominent pick-and-roll game and, of course, his lofty volume of 3-point attempts.

As for George, he would immediately provide Portland with another top-20 player to potentially build a postseason team around. The defensive range between George and Grant on the wing is considerable and Scoot Henderson would have no problem slicing down the middle of defenses before kicking out to George on the wing.

Nurkic/Grant/George/Simons/Henderson is a very talented, very explosive, and very balanced starting five. Portland would be the real deal.

Paul George is one year older than Lillard (33) and he's on a shorter-term contract that gives him the option to hit free agency next summer (with a player option for $48.5 million in 2024-25). The Blazers would presumably want to work toward an extension of some kind. George might also want long-term financial commitment out of Portland, but there are natural concerns tied to paying max money to an aging, oft-hurt star like George. Concerns the Blazers are very familiar with having dealt with Lillard.