Trade conversations centered around Portland Trail Blazers superstar Damian Lillard have existed for quite some time now. While they were on the doorstep of the NBA Finals in 2019 by making the Western Conference Finals, the Blazers have not gotten past the first round since. This franchise desperately needs to begin planning for the future, and Lillard's situation remains at the forefront of everyone's minds.

Despite remaining loyal all of these years to the franchise that drafted him sixth overall in 2012, Lillard is turning 33 years old in July and is not getting any younger. While still playing the best basketball of his career, the superstar guard has a massive decision to make regarding if he wants to stay with the Blazers or not, because his legacy may very well be on the line.

Leaving the Trail Blazers and possibly winning a title with a true, contending team could solidify Lillard's place as one of the best guards of his generation, as well as a potential spot in the Hall of Fame. Then again, staying with Portland and attempting to build this team back into a contending threat could unquestionably make him the greatest player in team history over Clyde Drexler.

With the NBA Draft taking place this past Thursday and free agency right around the corner, a decision on Lillard's future is expected very soon. So, here are three trade scenarios that we could see should the Blazers star request a trade after the franchise didn't trade the No. 3 pick for win-now help, instead snagging Scoot Henderson.

Miami finally lands Lillard

Miami Heat, Damian Lillard

Miami Heat Receive: G Damian Lillard, C Jusuf Nurkic

Portland Trail Blazers Receive: G Tyler Herro, G Kyle Lowry, F Nikola Jovic, MIA 2026 1st-Round Pick (Swap, More Favorable to POR), MIA 2027 1st-Round Pick (Unprotected), MIA 2028 1st-Round Pick (Swap, More Favorable to POR), MIA 2029 1st-Round Pick (Unprotected)

The one team that has been at the center of all Damian Lillard trade speculation has been the Miami Heat. Fresh off their run to the 2023 NBA Finals, the Heat have once again proven that they deserve to be in the championship conversation as long as their star duo of Jimmy Butler and Bam Adebayo is healthy and on the floor.

Miami is very high on Tyler Herro and has made it clear that they wish to keep him, but he would have to be the focal point of any trade package the Heat offer for Lillard. Not only would Portland want him in return, but Herro is the best player on this roster outside of Butler and Adebayo. They may not want to give the young guard up, but everyone within the Heat's organization would probably agree that getting Lillard makes them a much better championship contender.

As for the other parts of this deal from Miami, Kyle Lowry is nothing more than a salary filler who is in the final year of his contract, while Nikola Jovic is just 20 years old. Still growing and still a very raw prospect, the Blazers would be able to add a recent first-round pick with potential out on the perimeter.

Offering four total first-round picks (when including swaps) for Dame may seem like a lot, especially after Bradley Beal was just dealt to the Phoenix Suns for a plethora of second-round picks. The reason a package for Lillard would look different than that of Beal's trade package is because Lillard has proven to be a top-10 talent in this league and doesn't have a no-trade clause, though Dame can still effectively steer where he wants to go.

Devoting over $210 million to him over the next several years may not be advantageous with the new CBA rules and financial guidelines coming into play soon, but a trio of Lillard, Butler and Adebayo immediately has a chance to win a title in South Beach. Pat Riley has never been afraid to lay his rings down on the table to land a star, so as long as Miami's ownership is in, the Heat can pull the trigger on a deal like this.

The interesting aspect of this trade is getting back Jusuf Nurkic, a player Lillard is fond of and close friends with given all the years they have spent in Portland together. How he would fit in alongside Adebayo in the frontcourt is definitely worth questioning, but if the Blazers are to lose Lillard, they will want to cut back on overall costs. Trading Nurkic makes sense, and maybe they could squeeze another draft pick out of the Heat as a result.

Knicks enter Damian Lillard Sweepstakes

New York Knicks Receive: G Damian Lillard, G Keon Johnson

Portland Trail Blazers Receive: G/F RJ Barrett, G Immanuel Quickley, G/F Evan Fournier, NYK 2024 1st-Round Pick (Unprotected), NYK 2025 1st-Round Pick (Swap, More Favorable to POR), NYK 2026 1st-Round Pick (Unprotected)

While they have not been a topic of discussion in trade talks surrounding Lillard, keep an eye on the New York Knicks this summer. Something is brewing with this organization, because while it always seems like they are in a position to land a star, they always seem to lay low and add future value.

Owning the rights to 11 first-round picks through 2030, as well as valuable players such as Immanuel Quickley and Obi Toppin on rookie deals, the Knicks could easily get involved in trade chatter for any superstar that becomes available. After taking a step forward this year with Jalen Brunson and Julius Randle both having All-Star-like seasons, why not go after a star like Lillard?

Dame would be the missing piece for this team offensively, the Knicks would still be able to ink Josh Hart to a long-term deal and looking at their roster from a big picture standpoint, New York really wouldn't loose much if they were to go after the Blazers star.

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The Houston Rockets invested heavily into Fred VanVleet during the 2023 offseason. Houston gave the point guard a three-year, $128 million deal in a move that was meant to turn the Rockets from a rebuilding team into a championship contending one. The signing did just that, as the Rockets finished the 2024-25 regular season as the two-seed in a stacked Western Conference. VanVleet was the veteran presence and 3-point shooter that the team desperately needed, and he still might have a role with the Rockets going forward. Houston has a team option on his contract for next year, and they very well may pick it up. The Wichita State product reportedly wants to stay in Houston, but the point guard would be set to make over $44 million next season under his current contract. The Rockets and their guard recently pushed back the deadline on Houston's decision with VanVleet, and although reports suggest that they are interested in writing up a new, long-term deal, it isn't necessarily a guarantee that VanVleet will be playing for Houston next year. The Rockets blew him away with an offer he couldn't refuse back in 2023, and another team could so the same when/if he hits the open market this offseason. If VanVleet does become an unrestricted free agent, which teams outside of Houston would make the most sense for him to sign with? 1. Orlando Magic Jalen Suggs and Franz Wagner recently signed big deals with the Orlando Magic, and Paolo Banchero will be getting a mega contract extension here soon. Because of that, the Magic no longer have money to blow like they have had in recent years. That will make a deal for another big ticket free agent hard to pull off, especially considering the team signed Kentavious Caldwell-Pope last year. If Orlando can make the money work, though, then Fred VanVleet would be a great fit with the Magic. The Magic finished dead last in 3-point shooting this season, and VanVleet has made at least 2.5 deep balls per game in every season since 2018-19. VanVleet can hit shots form behind the arc off of the bounce or in catch-and-shoot situations. The Rockets were heavily reliant on his shooting expertise, so the guard would have plenty of familiarity getting up deep shots with high volume if he signed with the Magic. While undersized, VanVleet is a pesky defender, so he'd fit right in with a Magic team that has one of the best defensive units in the league. VanVleet could play alongside Suggs and give opposing teams fits. Ultimately, though, the Magic just need more shooting to get to the next level, and VanVleet is arguably the best shooter who could be available on the open market this offseason. 2. Brooklyn Nets A more realistic option for a VanVleet destination would be the Brooklyn Nets. The Nets are set up to have the most cap space this offseason, and they have a major need at point guard. With D'Angelo Russell and De'Anthony Melton hitting free agency this offseason, the Nets don't have a true point guard under contract for next season. Brooklyn needs to spend big this offseason, and they'd be smart to offer VanVleet a contract big enough that he'd have no choice but to leave Houston. VanVleet averaged 14.1 points per game last season, which was his lowest mark since 2018-19. He is trending the wrong way, but he still has enough left in the tank to give the Nets a few good seasons. 3. Portland Trail Blazers In the same way that the Rockets were looking to take the next step in 2023, the Portland Trail Blazers could use VanVleet's presence to get over the hump. The Trail Blazers have plenty of big man depth, as centers Deandre Ayton, Donovan Clingan, Robert Williams, and Duop Death are all under contract next season. Portland also has a lot of wing depth. Deni Advija started to look like a star late this past season, Toumani Camara is an elite defender, Shaedon Sharpe is a freakish athlete, and Jerami Grant is a proven scorer. The team is thinner in the backcourt, though. Anfernee Simons is a solid scorer, but Scoot Henderson has looked like a fringe draft bust since being drafted third overall. Portland shouldn't give up on Henderson completely, but there wouldn't be any harm in signing another guard. Like the Magic, the Blazers were one of the worst 3-point shooting teams in the NBA. VanVleet would improve that weakness, and in a stacked Western Conference, Portland needs all of the help they can get if they are to compete for a playoff spot.
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Lillard's production would be more than that of RJ Barrett's and Quickley's combined, plus he would help create one of the better scoring backcourts in the league alongside Brunson. As for Evan Fournier, he is a player the Knicks are going to be looking to move on from this offseason. Portland should be willing to take on his contract in order to dump him next offseason for cap relief.

In doing so, they would be rewarded with two immediate unprotected first-round picks and a 2025 first-round swap. Compared to the Heat's package, Portland would be receiving less value in terms of draft assets, but two young players in Quickley and Barrett to immediately give them building blocks for a rebuilding core.

The fact of the matter is that this is just the framework of a potential deal the Knicks and Blazers could explore, as New York has a lot more assets that they can offer up should they want to pursue Dame and should Portland want more value.

Keep an eye on the Knicks because if they do not go all out this offseason for a superstar, they definitely have the ability to do so at the trade deadline or next summer.

Lillard becomes Brooklyn's latest superstar

Damian Lillard, Mikal Bridges, Brooklyn Nets

Brooklyn Nets Receive: G Damian Lillard, F Kevin Knox II, G Keon Johnson

Portland Trail Blazers Receive: G Spencer Dinwiddie, G Joe Harris, G Cam Thomas, C Day'Ron Sharpe, MIA 2025 2nd-Round Pick (Top-37 Protected, via BKN), BKN 2026 2nd-Round Pick, PHX 2027 1st-Round Pick (Unprotected, via BKN), BKN/PHX 2028 1st-Round Pick (Swap, More Favorable to BKN, now POR)

Outside of the Heat, the Brooklyn Nets seems like the other top landing spot for Lillard if he asks out of Portland. After moving on from Kevin Durant, Kyrie Irving and James Harden within a year, some may think the Nets would not want to deal with the drama of housing another superstar player. However, they are in an intriguing position where one superstar talent like Damian Lillard could make them real threats in the Eastern Conference.

If this past NBA season has taught us anything, it is that the East is wide open despite the Milwaukee Bucks, Philadelphia 76ers and Boston Celtics being in firm control of the top spots in the conference. In the playoffs, anyone can make the Finals, which the Heat proved that this year. Adding Lillard to this younger, dynamic team that has the pieces to be an elite-level defensive team is absolutely something Nets ownership and the front office should want to explore.

Not only are Mikal Bridges and Lillard close friends, but the Blazers guard is the missing piece on a Nets team that struggled to score outside of Bridges late in the season. Seeing as they don't have much draft capital, the Nets are going to have to be willing to give up a lot.

Cam Thomas and Day'Ron Sharpe are both young, recent first-round picks the Blazers could add for future value, and taking on the contracts of both Spencer Dinwiddie and Joe Harris is advantageous. Dinwiddie and Harris are entering the final year of their respective contracts, meaning the Blazers would be able to free up nearly $40 million in cap room heading into next offseason.

As for the picks they would receive from Brooklyn, Portland would get two second-round picks in 2025 and 2026, as well as an unprotected 2027 first-round pick from Phoenix and a swap in 2028. The Nets are set to receive the more favorable of their own and the Suns pick in 2028, which would now go to Portland. The Blazers would have the option to take the most favorable pick that year.

Maybe the Heat and Knicks can offer better overall packages for Lillard, but the Blazers would be able to get nearly $40 million off their books right away while adding valuable, unprotected draft picks in future years that could end up being lottery selections.