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Which Team Should Trade for Damian Lillard?

The six-time All-Star has not requested a trade, but his future in Portland is up in the air.
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There has not been an official trade request to date by Portland star Damian Lillard. That hasn’t stopped speculation about his future with the franchise who drafted him nine years ago.

Lillard, a six-time All-Star, denied a report that a trade request was imminent, but he made it clear he wants to see upgrades around him. Portland is in the bottom third of the league in projected cap space. The biggest moves it can make are moving on from Lillard or his running mate, C.J. McCollum, long the subject of hypothetical trade packages.

Currently, Lillard is in Tokyo with Team USA while his future with the Trailblazers is being toiled over stateside. He recently said, “The conversations that need to be had are being had.”

It’s reasonable to assume some of those conversations could end with Lillard playing next season in a different jersey. He would command a high asking price if put up for trade. Below are four potential trade packages that Portland could field for its franchise player.

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1. Miami Heat

Heat acquire: Damian Lillard

Trailblazers acquire: Tyler Herro, Kendrick Nunn (sign and trade), Goran Dragic (sign and trade), Precious Achiuwa, 2024 first-round pick (via Heat), 2026 first-round pick (via Heat)

Bringing Lillard to Miami would create a truly menacing Big 3 alongside Jimmy Butler and Bam Adebayo. And Lillard is an instant offensive upgrade for a team that was near the bottom of the league in points per game a year ago and hasn’t had a 25-points-per-game scorer since LeBron James in the 2013–14 season. Tyler Herro was said to be the crux of a potential James Harden trade a season ago. His value has diminished since then, but he could still headline an offer for Portland’s star.

None of the players the Trailblazers would acquire in this trade push the needle toward a championship. This is about getting assets and youth. Dealing Lillard is a sign that the current roster, with one of the best players in basketball, is not enough to compete in the West. Getting three players in Herro, Nunn and Achiuwa who are 25 or younger pushes back the timeline for first-year coach Chauncey Billups.

2. Philadelphia 76ers

76ers acquire: Damian Lillard

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Trailblazers acquire: Ben Simmons, Tyrese Maxey, 2023 first-round pick (via 76ers), 2023 second-round pick (most favorable via Atlanta, Charlotte or Brooklyn), 2026 first-round pick (via 76ers)

Lillard is the opposite of Ben Simmons. He’s a volume shooter who lives in the fourth quarter and doesn’t earn his money on defense. Simmons is allergic to jumpshots, has shown a tendency to defer in big moments and has two All-Defense nods in four seasons in the NBA. The marriage of Simmons and Joel Embiid has been a nightmare for spacing in Philadelphia, where the backcourt of Lillard and McCollum has been a turnstile defensively. This deal improves both teams’ biggest weaknesses or concerns.

Simmons’ value sunk after his flameout in the postseason, which is why 76ers general manager Daryl Morey would need to sweeten this deal with draft capital and a capable young guard in Maxey. Lillard, on the other hand, is at the peak of his powers and value. He lit up the Denver Nuggets for 55 points during his team’s first-round playoff exit and was named to his fourth consecutive All-NBA team. Trading for Lillard could vault Philadelphia forward after its recent playoff disappointments, while Simmons could keep Portland in the playoff picture out West.

3. New York Knicks

Knicks acquire: Damian Lillard

Trailblazers acquire: RJ Barrett, Immanuel Quickley, Obi Toppin, Kevin Knox, 2022 first-round pick (via Knicks), 2024 first-round pick (via Knicks)

This is a true haul of players and assets for Lillard. The oldest player the Trailblazers would be getting back is Toppin, who’s just 23 heading into his second year in the NBA. Barrett and Quickley both flashed their upside during the Knicks playoff run while Toppin and Knox are both low-risk acquisitions and recent first-round picks who could benefit from a team change.

Though New York really put things together this season behind Julius Randle’s All-Star campaign, this trade leaves the Knicks with a one-two punch of Lillard and Randle and no third star on the roster. That’s a strong duo and their games complement each other, but it doesn’t hold up against Brooklyn’s Big 3 or Golden State’s. New York is expected to have the most cap space in the NBA this offseason, though. So there is room for the front office to bring another dominant trio to New York City. Teaming up with Lillard and Randle in Madison Square Garden is a rather attractive proposition to free agents.

4. New Orleans Pelicans

Pelicans acquire: Damian Lillard

Trailblazers acquire: Lonzo Ball (sign and trade), Brandon Ingram, 2022 first-round pick (via Lakers), 2024 first-round pick (via Pelicans)

Acquiring Ball and Ingram keeps the Trailblazers competitive. Ball would start immediately in the backcourt alongside McCollum, and he’s a defensive upgrade from Lillard. Ingram would also satisfy Portland’s long standing need for an offensive-minded forward. And rather than just trading for youth and picks, the Trailblazers get a pair of 23-year old stars and draft compensation.

Pairing Lillard with franchise cornerstone Zion Williamson could quell the concern of those in Williamson’s circle about the team’s direction. New Orleans has missed the playoffs the past three seasons and are on their third coach in as many years. The team keeps running it back with the same set of guys and winning 30ish games—not enough to make the playoffs in the West and too many to get back in the range of lucking into a generational talent like Williamson at the top of the draft. This move makes a perennial near playoff team look much more like a contender.

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