Damian Lillard's future does not appear to be with the Portland Trail Blazers. Despite spending the last 11 years as the face of the franchise, remaining loyal to them through thick and thin, Lillard is wanting more as he nears the back half of his illustrious career.
The Trail Blazers have slowly been declining in the Western Conference and they have been going through a soft rebuild over the last couple of years. When they traded Lillard's right-hand man, CJ McCollum, it just seemed like a matter of time before the superstar point guard would want to find a new team. This summer, he made the request to the Blazers front office and the waiting game has been going on ever since.
Unlike James Harden's situation with the Philadelphia 76ers, Lillard still has a solid relationship with Portland and is not going to create a toxic environment. Even though he wants to be traded, the seven-time All-Star and All-NBA guard is being patient, allowing the Blazers to evaluate all of their options.
At the same time, Lillard has made it clear that he wants to join the Miami Heat and compete for a championship in South Beach. This has put his organization in a tough spot, especially with the Heat not willing to budge on their offer for Dame seeing as he only wants to play for them.
Portland is said to be taking their time involving Lillard and general manager Joe Cronin is evaluating all of his team's options. Even though he may want to go to the Heat, that does not necessarily mean the Blazers need to trade Lillard there. This franchise is going to take the best deal that they can get, which could result in another team coming in and convincing the star to play for them instead.
Overall, this is highly unlikely to happen. Dame's mind is made up and it is just a matter of time before the Trail Blazers cave on their intentions. The Heat do have some valuable assets to offer up and if Lillard refuses to play for another team, then Portland's options are severely limited.
As far as Lillard possibly going to another team, it is never a bad time to speculate what potential deals could look like. Even with a lot of false narratives being created, it is at least worthwhile to consider and evaluate what the Toronto Raptors and Oklahoma City Thunder could offer for the superstar.
Damian Lillard to Toronto?
Out of all the teams in the NBA, the Toronto Raptors are in one of the most unique spots because of what has transpired the last handful of seasons. Following their miraculous run to a championship in 2019, the Raptors have missed the playoffs in two of the last three seasons. Nick Nurse is no longer the head coach after being fired at the conclusion of the 2022-23 season and Fred VanVleet is no longer with the team either.
Nurse joined the 76ers to take over for Doc Rivers and VanVleet signed a three-year, $130 million contract with the Houston Rockets in free agency, becoming the highest paid undrafted player in NBA history.
Nobody can really fault VanVleet for making this decision, as there are very few opportunities for players to see this kind of money over the course of their career. From Toronto's point of view though, this decision has put the organization directly in the middle of a crossroads with the path to a rebuild inching ever so closer.
However, executive Masai Ujiri and this front office have never seemed to give up and go through a full rebuild. Much like how they did with Kawhi Leonard ahead of the 2018-19 season, the Raptors could be willing to move a lot to bring in Lillard, a player who could immediately put them back on the championship path.
Pascal Siakam and Scottie Barnes would be the “untouchables” in this trade scenario, making OG Anunoby, Gary Trent Jr., Precious Achiuwa and rookie Gradey Dick the team's best assets. Trent is an interesting name to discuss not just pertaining to this hypothetical scenario for Lillard, but in general.
Early on in free agency, TNT and Bleacher Report's Chris Haynes reported that Trent and the Raptors were nearing an agreement on a new long-term extension. Well, months have gone by and the 24-year-old has yet to sign any new deal with the team. This could be nothing, but it is at least notable because why wouldn't the two sides finalize the terms of their deal?
It is possible that Trent had second thoughts about remaining in Toronto after seeing VanVleet depart in free agency. Another possibility is that he does not want to commit to the team and lock himself in on a new multi-year deal if Siakam is going to be traded.
There are so many question marks surrounding what the Raptors future looks like and it's not hard to believe that their own players are having doubts about the state of the organization.
Pertaining to Lillard, Anunoby would be the headliner in any potential deal with the Blazers. His two-way prowess is something a lot of teams have been intrigued by through the years and the former first-round pick is still just 26 years old. On a new team where he can be a featured star instead of a secondary talent, Anunoby could blossom into one of the best two-way players in the league.
The idea of forming a package around Anunoby, Trent and draft picks for Lillard would certainly be an appealing situation for the Raptors, but it is hard to see the Blazers finding value here unless they were to get other teams involved. They already traded Trent once before and while Anunoby is a really solid player, can he really become more than he currently is? Portland needs to consider all scenarios and this one with Toronto does not seem worthwhile.
Damian Lillard to Oklahoma City?
Compared to the Raptors, the Oklahoma City Thunder have a plethora of assets that they could potentially offer up not just for Lillard and any other superstar they want to target. General manager Sam Presti has done a fantastic job of assembling draft picks and high-potential talents through the draft over the years, leading the Thunder to a point where they are about to take a massive step forward.
Shai Gilgeous-Alexander emerged as one of the best scorers in the league a season ago and he is preparing to enter the 2023-24 season as a potential MVP candidate. There is no better time for the Thunder to pull off a trade for a player like Lillard than right now, especially since he would pair with Gilgeous-Alexander to form the best backcourt duo in the league.
Oklahoma City has a wide array of assets to offer as well, especially since only SGA and Chet Holmgren would be their only true “untouchables.” While it is unlikely that they would be willing to trade Josh Giddey, the Thunder would probably part ways with him if they truly wanted Lillard.
Luguentz Dort, Aleksej Pokusevski, Jalen Williams, Ousmane Dieng, rookie Cason Wallace and various first-round picks over the next several years round out the list of assets Portland could potentially bring back in a trade for the Blazers guard.
The problem here revolves around the Trail Blazers and their willingness to not only deal Lillard, but trade him to another Western Conference team. When a trade does occur, it is very likely that Cronin and the Blazers will want to relocate Dame to a team in the Eastern Conference, that way they do not have to compete against him.
Not only would trading Dame to the Thunder keep him in the West, but he would remain in the same division as the Blazers. As much as this scenario would work wonders for Oklahoma City as they quickly rise, it is just very hard to imagine Portland showing a level of willingness to trade him to another Western Conference team.