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Why blockbuster trade could lead to happy ending for both Damian Lillard and Portland Trail Blazers

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Credit: Jaime Valdez-USA TODAY Sports

Technically, Damian Lillard didn’t receive his wish to play with the Miami Heat. Technically, the Portland Trail Blazers eventually accommodated Lillard’s trade request.

Despite the murkiness both parties experienced with their divorce following a previously fruitful partnership, both Lillard and the Trail Blazers ultimately will experience the best outcome through their respective circumstances.

Lillard will still join another NBA championship contender (Milwaukee Bucks) with a superstar that he has already said he would love have as a teammate (Giannis Antetokounmpo). The Bucks now have the league’s best trio with an elite point guard (Lillard) to pair with their elite big man (Antetokounmpo) and elite wing player (Khris Middleton). And such a move certainly should assuage Antetokounmpo’s questions on whether the Bucks fit in his long-term future.

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The Blazers completed a three-team trade with Milwaukee and Phoenix that ensures they can remain a playoff contender with their young team by acquiring a proven two-way player (Jrue Holiday), a talented big man (Deandre Ayton), a young prospect (Toumani Camara) and draft capital (Bucks’ 2029 first-round pick) in exchange for their generational star (Lillard), a proven big man that has durability issues (Jusuf Nurkic) and an inconsistent young player (Keon Johnson). The Blazers now have another trade chip (Holiday) they can offer to Miami. As Lillard became increasingly frustrated with in recent seasons, the Blazers won’t seriously compete for a championship this season. But much like during Lillard’s tenure, the Blazers will become a dangerous playoff team that can eventually enter the championship-contending mix in future years.

Damian Lillard and Blazers were both winners in trade

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Rob Gray-USA TODAY Sports

It’s ironic both parties experienced a win-win situation during a time when franchises and superstar priorities don’t always align. That initially applied both to Lillard and the Blazers. A year after agreeing to a new extension, Lillard’s loyalty to Portland cracked amid his frustration with the organization’s inability to construct a title-contending team around him. After experiencing appreciation for Lillard leading them to eight consecutive players and eventually becoming the franchise’s all-time leading scorer, the Blazers declined to acquiesce to Lillard’s trade request — at least not on his terms.

Those around Lillard suggested teams outside of the Heat shouldn’t trade for him because he would have no interest in playing for them. Those in the NBA, including the Blazers, didn’t believe Lillard would do such a thing because of his professional track record. Those around Lillard conceded the same thing, while at least hoping that his contributions earned him enough capital for the Blazers to do right by him.

Initially, Blazers conveyed feeling comfortable with keeping Lillard entering training camp. Just like Kevin Durant showed last season in Brooklyn following his off-season trade request, the Blazers trusted Lillard would still produce and help them win games without becoming a disruption. Besides, the Heat had nothing the Blazers wanted outside of the two stars that Lillard hoped would become his teammates (Jimmy Butler, Bam Adebayo). Perhaps the Blazers would just follow the Nets route and wait for a better deal to emerge leading into the NBA’s trade deadline.

Nonetheless, both parties benefitted from the Blazers finding a suitable deal before training camp started. The Blazers avoided putting Lillard and their young roster in an awkward situation. The Blazers found a deal that will accelerate their growth rather than hinder it. And ironically, Lillard landed on a team that gives him a better shot at winning his first NBA championship than Miami could.

That’s not to say there are not any risks involved.

The Bucks just parted ways with Holiday, who became a needed complementary scorer and their best defender. The Blazers acquired a center (Ayton) has not yet proven he can stay consistent with his play and maturity. Both parties can minimize those risks, though. The Bucks still acquired Lillard while retaining plenty of star and role-player depth. The Blazers could feature Ayton more than the Suns’ top-heavy team likely could. And unlike this past summer, both the Blazers and Lillard can concentrate more on basketball than their respective uncertain futures.

Rarely in this era does such an outcome happen. With player empowerment increasing for better and for worse, star players usually land at their preferred destination. With franchises under increased pressure to win immediately, some make win-now moves that backfire quickly or roster overhauls that only ensures job security without a successful rebuild.

Portland and Lillard avoided this outcome. Lillard made the long overdue decision to ask the Blazers to trade him because it seemed implausible he could ever win an NBA title with them. The Blazers weighed all options at a deliberate pace to ensure they could stay in the playoff mix with a young roster. Because of that, an initially tough breakup eventually turned into what should become a happy ending.

Mark Medina is an NBA Insider at Sportsnaut. Follow him on TwitterInstagramFacebook, and Threads.