Damian Lillard's time as the face of the Portland Trail Blazers is coming to an end. Through thick and thin, he has remained with and given the Blazers multiple chances to improve their championship outlook, yet both sides appear to be ready to move on after the seven-time All-Star requested a trade this offseason.

Then again, Portland is not going to just trade Lillard for the sake of trading him. In order to deal a generational talent like him, the Trail Blazers are going to need to get back a substantial amount of value and this is exactly the thinking of GM Joe Cronin and everyone inside the walls of this organization. The only problem, though, is that Lillard and his agent, Aaron Goodwin of Goodwin Sports Management, have made it very clear that the Blazers star wants to play for and only play for the Miami Heat.

Fresh off their run to the NBA Finals as the 8-seed in the Eastern Conference, Miami is ready to form a new “Big 3” by adding another All-Star talent next to Jimmy Butler and Bam Adebayo. Lillard seems like the obvious choice for this franchise not only due to his interest in going to South Beach, but due to their lack of backcourt production.

The Heat have been in contact with the Blazers regarding their star player, yet trade talks have not escalated in any fashion and no real deal has materialized, league sources told ClutchPoints. Not much progression has been made on any trade talks involving Lillard league-wide simply because of his unwillingness to accept a trade anywhere but Miami. This has drawn the attention of Adam Silver and the NBA, resulting in them having to step in to warn Lillard and Goodwin about what is being said.

Consequences of the NBA's Lillard memo

Miami Heat, Portland Trail Blazers, Damian Lillard, Adam Silver

In a memo sent to all 30 franchises on Friday, the league stated that they had interviewed Dame and his agent, as well as teams Goodwin had spoken with in recent weeks regarding the comments that his client would only welcome a trade to the Heat. With this situation turning out to be a game of “he said, she said,” the NBA warned both Goodwin and Lillard, stating that they will “subject Lillard to discipline” should he not fully perform the services outlined in his contract in the event of a trade.

Basically, the NBA made it clear that any team in the league can make a trade with the Blazers for their All-Star guard and that he will be punished if he holds out and refuses to play if not traded to Miami. This memo also made it clear to the NBPA that the league will not be going down a path where players will dictate where they are traded to and that any player/agent that follows in Lillard's footsteps will be subject to discipline as well.

This was definitely an eye-opening statement coming from the NBA, as it shows they are very aware of what is happening right now and how every team in the league may not- and does not- have an equal opportunity to trade for Lillard. While a player does have every right to work with their team on a potential trade, they do not necessarily have the final say. In Lillard's case, his agent saying that his client would only play for the Heat has caused the trade market across the NBA to crash.

As things stand right now, no team outside Miami has really shown a lot of trade interest in Lillard simply because of his stance on the matter. There are a handful of teams who could utilize him right now, but if Lillard refuses to play for them, what is the point of giving up various assets and draft picks to acquire him?

It has always been the Heat or nothing for Lillard in trade talks this summer and even after the NBA sent out this memo, it is hard to imagine that viewpoints have been altered. Everyone knows that the veteran All-Star wants to be in Miami and the damage that has been done in trade negotiations as a result cannot be changed.

From the Blazers' point of view, they do not want to trade Lillard to the Heat unless they can capitalize on his high value. Miami's lack of overall assets and the fact that other teams who have expressed interest in Lillard can offer up what Portland wants has created a hold up in the situation. On the other side of things, from Miami's point of view, they do not want to give up a ton of assets for him because the Heat know Lillard wants to play for them.

There truly is no side to blame here, as the Trail Blazers and Heat are both right for feeling how they do about these trade negotiations. It is Lillard and his agent that have created the predicament, and as training camp inches closer, no end appears to be in sight for this saga.

Evaluating Miami's assets

Miami Heat, Portland Trail Blazers, Damian Lillard, Tyler Herro

When you look at the Heat's roster right now and what they have to offer up, their best assets include Tyler Herro, Caleb Martin, first-round pick Jaime Jaquez Jr. and Kyle Lowry's expiring $29.6 million contract. As far as draft picks go, Miami cannot offer a first-round pick outright until 2027 due to prior obligations and there are no guarantees they could even trade this pick due to protections they have on their 2025 first-round pick owned by the Oklahoma City Thunder.

In terms of tradeable draft picks they do have, the Heat's best offer for Lillard could include first-round picks in 2027 and 2029, as well as swaps in 2028 and 2030. They cannot send a swap for 2024 due to the Blazers not owning a first-round pick next year and the Heat's pick in 2026 is currently tied up due to this prior trade with the Thunder. Their pick in 2027 can be dealt with stipulations, but things can get really messy with what picks would then become swaps and what not. Basically, the best Miami can offer is two outright picks and two first-round swaps.

There is value to be had with outright picks from 2027 and beyond, but none of the players Miami has really equates to the value Lillard holds. Herro would likely be re-routed to a third team and then there are hurdles to get over regarding what this third team would be willing to give up to help facilitate the trade.

It does seem inevitable that Lillard will end up in a Heat uniform when all is said and done, yet nothing appears to be imminent, and the Blazers are in no rush to make a deal. They know that Lillard's value is going to remain the same, seeing as he is a Top 10 player in the league right now- and the good news for Portland is that they have some talented, youthful players they can immediately begin to build with.

Anfernee Simons, Shaedon Sharpe and third overall pick Scoot Henderson are all young, dynamic players in the Trail Blazers' backcourt, and they will be the ones this organization turns to in the immediate post-Lillard era. Already having a foundation set up, finding the right complimentary pieces and assets in a trade this offseason is key for Portland. This is why striking a deal with the Heat has not happened yet and this is why no progression has been made.

Everything leads back to the main question on everyone's minds: “Will Damian Lillard be traded before the start of the 2023-24 NBA season?” 

At this time, the Blazers seem more than willing to wait around. While he wants to go to the Heat, we should not rule out the possibility of the Trail Blazers trading Lillard to another team that is willing to sacrifice a lot of value. Trading for Lillard is a massive risk for any team in this league to take, especially given the notion that he will only play in Miami. Whether or not the league's latest memo impacts this trade situation is yet to be known.