The Portland Trail Blazers have missed the playoffs for two consecutive seasons now and it seems more likely than not that changes are on the way.

Portland’s front office has struggled to build a winning team around its superstar point guard Damian Lillard in the aftermath of its Western Conference Finals appearance back in 2019, but this high-water mark of their 11-year partnership is more of an outlier than it seems.

Over the last seven seasons, the Blazers were eliminated in the first round four times, failed to make the postseason twice, and had that one run to the West Finals. This team has been quite mediocre for several years and it is reasonable to think that these two parties may soon be heading in different directions, especially after Portland won the third overall pick in this month’s NBA Draft.

A full-on rebuild may be on the way for the Blazers and Lillard is well aware of this reality. In a recent interview, the seven-time NBA All-Star reiterated his loyalty to his current team, but also singled out the Miami Heat and Brooklyn Nets as potential destinations for him if Portland’s leadership decides to focus on their long term future instead.

The fact that the Heat and Nets are in the East makes trading away Lillard an easier pill to swallow for the Blazers as it is unlikely that they are willing to help one of their in-conference rivals.

Lillard shared that Miami is an obvious choice and shared that a major reason for this is his close relationship with Bam Adebayo. The Heat will have to part with Tyler Herro to make this deal work though they may have to give up multiple young pieces to entice Portland.

Two of Miami’s three players born in the year 2000 or later, breakout postseason star Caleb Martin and promising rookie Nikola Jovic, appear to be the most promising pieces that could be included in a trade to snag Lillard. Multiple future draft picks are likely to be involved as well and a salary cap filler will be needed to make it work.

A hypothetical “Big Three” of Lillard, Adebayo, and Jimmy Butler would be a sight to behold and immediately put the Heat, who are currently battling for the title, as favorites to make the NBA Finals once again.

Meanwhile, Brooklyn was also mentioned for a similar reason–Lillard’s friendship with their recently acquired star Mikal Bridges. The Nets have a plethora of tradeable pieces in the wake of their midseason trades that sent away Kevin Durant and Kyrie Irving so it will be difficult to outbid them if the time comes that Lillard is made available.

Cam Thomas and either Cam Johnson or Dorian Finney-Smith come to mind as possible players that Brooklyn could include in a Lillard deal.

One crucial take away from Lillard’s statements is that the two players that he mentioned–Adebayo and Bridges–are highly versatile on both ends of the floor and, theoretically, make for perfect on-court partners alongside Lillard.

Despite these tantalizing scenarios, there remains a strong likelihood too that Lillard will stay on the Blazers. They could package the third pick in this year’s draft for the co-star that they have long needed such as Karl-Anthony Towns, Jaylen Brown, or Zach Lavine. The relationship between Portland and the 2013 NBA Rookie of the Year has deep roots and should not be overlooked here.

With the NBA Finals about to conclude, silly season is once again back in vogue in the NBA and these Lillard musings are only the tip of the iceberg. It will be interesting to see what team the 32-year-old guard will be on come opening night this October and also who will be taking the floor alongside him when the new season tips off.