What Is The Best Destination For Damian Lillard?

By Saransh Sharma, Rohan Krishnan, Pranav Thiriveedhi, Anish Dhondi, & Nikhil Pradeep

Damian Lillard is a superstar who has given everything to the Trail Blazers franchise and the city of Portland. Consistently playing like a top-10 NBA player for the last few seasons, being an incredible scorer, facilitator, and leader for this team, taking this team as far as the Western Conference Finals (2019), Lillard has done everything he possibly could in Portland. But like many superstars who have dedicated years to their franchises, like James Harden and Anthony Davis in recent memory, Lillard and the Blazers seem to fall short every single year. That leads to trade rumors, frustration, and more build-up, and eventually overtake a player, as the reality that their team cannot win a championship given the current state of the NBA, despite their incredible performances and leadership night-in and night-out, becomes a reality. While Damian Lillard denied that he requested a trade, to say he has not considered wanting out of Portland is ridiculous to say. Lillard, in his press conference addressing the trade request rumors, said that while he did not request it, he does not see Portland as a championship team with their current roster and coaching staff. Portland is going into a make-or-break season to get Lillard a championship, and the odds are very slim. This may be the last season for Lillard in Portland unless they win a ring or make serious championship moves, so if that is the case, here are our best-case scenarios and destinations for Lillard:

Saransh’s Best Destination For Dame: New York Knicks

There are only a few teams that have trade packages for Lillard: Philadelphia, Miami, Boston, New York, and maybe Toronto. However, the Knicks would have enough assets and also have the cap space to get a max-level player or multiple young players and role players alongside their core of Julius Randle, Mitchell Robinson, and Immanuel Quickley. Not to mention the possibility of keeping Derrick Rose around this season via free agency. Lillard not only gets a much better team around him than that in Portland, but he gets to be on a much younger team, be the leader, and also not just be ‘the guy’ on this team, but the true face of the franchise, something the Knicks have not had since their days with Carmelo Anthony. The fountain of youth that Lillard will be surrounded by will give the Knicks enough years for them as a franchise to build themselves into a championship team and prove to Lillard that his time leaving Portland would not go to waste. 

The fit with New York would also satisfy Portland best, giving them a solid player like RJ Barrett, who is very young and has star potential. They also would likely receive Kevin Knox, a former first-round pick for the Knicks who did not fit that team and their philosophy, but getting a fresh start in Portland will do wonders for him. On top of all that, the Knicks have a boatload of draft capital they can trade-off to Portland for Lillard for them to go all-in on contending for a championship, while Portland goes all-in on rebuilding.

Overall, a move to New York guarantees Lillard three things, the first being that he gets to extend his career with a fountain of youth around him, allowing him to play fewer minutes at times during the regular season to stay fresher in the Playoffs and compete for a championship. This move could help him even extend his prime years. Second, he will play in a defense-first system led by Head Coach Tom Thibodeau while still being around a good and balanced offense. Lillard will not need to drop as many 60-point efforts just to see his team lose, as he can rely on other guys, along with himself, to get stops as a unit. Third, he competes for a championship. Portland for years has been behind in the Western Conference, and while they have gotten to the Western Conference Finals in the past, they have never presented a threat to anyone in the West as championship contenders. New York, with an up-and-coming roster, one of the league’s best players in Lillard, and a strong presence already in the Eastern Conference, this team can be right up there with the best of them, year after year.

Rohan’s Best Destination For Dame: Philadelphia 76ers

The Philadelphia 76ers can make the most tempting offer thanks to one player: Ben Simmons. Yes, Simmons was lackluster in the 2021 postseason and was the biggest reason for Philadelphia not advancing to the Eastern Conference Finals. However, his trade value is still high around the league as he is an excellent defender and playmaker and only 25 years old. I feel like a package of Ben Simmons, Matisse Thybulle/Tyrese Maxey, and 1st round picks are more valuable than what any other team can offer. By pairing up Dame with Embiid, the Sixers would be in championship contention for years to come. Damian Lillard is just entering his 4-year contract, and Joel Embiid is locked up for the next 2 years. Lillard has shown he is not afraid to shoot from anywhere and would add a lot of spacing. Also, Dame is a solid playmaker, and working the pick and roll with Embiid would be a scary sight for opposing teams. The Sixers need to keep in mind that their window is now and they have to do whatever it takes to get a superstar like Lillard on the market.

Meanwhile, Portland would be getting an infusion of young talent to stay competitive in the West. Ben Simmons would immediately improve the Blazers’ poor defense, and CJ McCollum can blossom as the 1st option. McCollum has averaged 28.1 points, 6.2 assists, and 5.0 rebounds in 33 games without Damian Lillard in his career. Portland will also be getting Tyrese Maxey or Matisse Thybulle, who both have lots of potential, as Thybulle is one of the best defenders in the league, and Maxey provided a big spark for Philly in these playoffs. 

I would be shocked if Philadelphia is not at the top of Lillard’s list. He would get to play next to MVP runner-up Joel Embiid and automatically compete for a championship. Also, the Sixers have Seth Curry and Tobias Harris, who are both solid supporting options. Damian Lillard would have less pressure on him, and he would make Joel Embiid’s life easier as well, allowing him to play more minutes. With the addition of Dame, Philly would give nightmares to teams around the league and be at the top of the Eastern Conference for at least the next couple of years. 

Pranav’s Best Destination For Dame: Boston Celtics

Over the last few years, Boston has tried many ways to get back to the Finals with a few different point guards to note. A chance with Kyrie Irving for 2 seasons, and then Kemba Walker for the next 2 seasons, yet both failed, and the championship chase is back to square one. But Dame Lillard penciled into the starting lineup with Jayson Tatum and Jaylen Brown would provide that much-needed perimeter offense that the Celtics are in dire need of, immediately putting them with Milwaukee and Boston as East favorites.

The only problem is the offer. What would the Celtics hand over to the Trail Blazers to get the generational All-Star? If I was Brad Stevens, I would not want to break up the Tatum-Brown duo that Boston worked so hard to build around. A package of Marcus Smart, Tristian Thompson, Romeo Langford, Aaron Nesmith, or some combination of young players along with Smart and Thompson, along with first-round picks from 2022, 2024, and 2026 would do the job. A hefty price tag that undoubtedly puts Boston in championship contention. Marcus Smart and Tristan Thompson would be excellent additions defensively to the Trail Blazers, and the infusion of youth would put Portland in a great position to rebuild completely.

Anish’s Best Destination For Dame: Stay in Portland or Trade to New York Knicks

Now as a Portland Trail Blazers fan, the obvious choice would be for me to say that Dame stays with the Blazers. He is a franchise superstar like no other and is still under contract till 2025, meaning that if he traded, the return would be massive. However, the more realistic scenario I see is that CJ McCollum traded this upcoming season for someone who can fill his role not only offensively but defensively too. The Blazers have reportedly declined offers for CJ McCollum because it does not fit their timeline. The Blazers have no use for first-round picks right now if they want to keep Lillard, and their primary goal is to make the team as good as possible for next season. 

Damian Lillard is a humble guy who will speak his mind when he wants to say something rather than the entire world claiming he requested a trade. I will not believe Lillard requests a trade this season unless I hear it directly out of his mouth, but do not get me wrong, the situation in Portland right now is not pretty. The Portland Trail Blazers are the definition of being a mediocre team. They have consistently made the playoffs for the last 8 seasons, but in this time, they were only able to make it to the Western Conference Finals once (2019, swept by Golden State). That Warriors team was stacked, and Portland was not favored to win, but 2019 was the absolute breaking point. This season, Portland had no excuse for losing to a Nuggets team missing its 2nd best player, especially since that Nuggets team got swept by the Suns in the next round. Lillard gave it his all the entire series, even having a 55-point Herculean effort in a Game 5 loss, but his team absolutely sold that game, and Lillard finally decided it was time to challenge the front office and their sense of urgency. I believe he will force the front office this off-season to make a move and make this right, or he requests a trade.

Now, consider a scenario in which the front office does absolutely nothing this offseason like in previous seasons and Lillard requests a trade, only a few teams with enough assets to satisfy Lillard and Portland’s needs. These teams include the Knicks, Celtics, Sixers, Raptors, maybe Miami, and not the Lakers, despite the hype. Lillard on the Knicks seems most beneficial and appealing for him, and basketball fans like myself. This situation would fill all the holes of his past as Portland: a historically horrible defensive team, and being able to play in one of the biggest markets in the world. Now when it comes to what the Blazers get in return, a package revolving around RJ Barrett along with other assets and first-round picks could work out and make this all work. Other teams like the Celtics would not work as they have no good reason to trade Jaylen Brown as he will develop alongside Tatum and there is no reason to tinker that duo. The Sixers are also on the edge because we know Ben Simmons is on the table, but I believe McCollum is more likely to be traded for him. I would not be surprised if Dame gets traded to some team in a smaller market like Toronto or Utah, but in the end, he wants to compete and win a championship, and it is doubtful he cares about where. All I know is there is no chance Lillard forms a crazy superteam, as he has been against the idea his whole career. This would eliminate the already-unrealistic shot of the Lakers trading for him.

The ideal scenario is that the Blazers trade McCollum this offseason for Ben Simmons. Ben Simmons could fill the Draymond Green-type role, being the offense-leading point forward and being the defensive stopper Portland needs. The Blazers will re-sign Powell and run a Lillard, Powell, Covington, Simmons, and Nurkic starting 5 in this scenario. Another scenario I could see is McCollum to the Celtics for Marcus Smart and Robert Williams, which would fill Portland’s holes defensively. All I know is that the Blazers need to make a major trade if they want Lillard to stay, and there is no one besides McCollum with enough trade value.

Nikhil’s Best Destination For Dame: The Philadelphia 76ers

Objectively speaking, the Blazers and the Sixers have exactly what to offer for a perfect trade between the two teams, yet they both seem hesitant to take a risk and improve upon what they already have. From the Trail Blazers point of view, it is clear as day that their team is not going anywhere as far as young talent is concerned and if they want to rebound in the next few years without Damian Lillard, they need to either tank and draft accordingly (ex. Oklahoma City Thunder), or trade Dame for a good stash of young players and picks. An emphasis on defense and playmaking is a must this offseason and the future, and whichever route Portland chooses to go needs to revolve around this central notion. The 76ers on the other hand have an MVP candidate in Joel Embiid, and a rather perfect supporting cast containing the likes of Tobias Harris, Danny Green, Seth Curry, and the most pivotal of all, Ben Simmons. Philadelphia came off a strong but still underwhelming playoff performance this season and is obviously in win-now mode given the prime of Joel Embiid and the lack of a large number of young players. Simmons, as we all know, has been lackluster as of late and simply can not shoot the ball consistently to warrant his All-Star persona. Again, both teams have issues that both teams can solve using the tools each other possesses.

Simmons’ defense and his point-forward playstyle fit Portland beautifully and fix some of the problems this franchise has had for years on end now. Couple him with a few young players that the Sixers have to offer like Matisse Thybulle and Tyrese Maxey (Thybulle being an excellent defender & Maxey being a great scoring guard), this trade could do wonders for Portland. If Portland wants to fully immerse into rebuild mode, they can easily move CJ McCollum to get even more picks/talent and position themselves perfectly for the future. Given the caliber of Damian Lillard, picks can be added or swapped in place of players to sweeten the deal as well, and in my opinion, Philadelphia is willing to do anything to improve their team and offload Ben Simmons.

The Sixers receive quite possibly the best clutch player in our league today in Damian Lillard, and once paired with Joel Embiid, seems to form one of the deadliest duos this league would see today. Once placed into an already free-shooting offense containing Danny Green and Seth Curry, you inadvertently form an offense that rivals, and in my opinion beats that of Brooklyn when healthy. This trade, if successful, immediately propels Philadelphia into championship contention and solves a lot of their offensive production issues.

In many ways, Philadelphia seems like the best trade suitor for Damian Lillard, especially given the unwillingness of Boston to deal Jaylen Brown and Miami to deal anyone on their roster and the comparative lack of assets from New York and any other team in the league. If Dame truly wants out of Portland, Philadelphia looks to be the best possible place to win that elusive ring.

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