Damian Lillard Traded to Milwaukee: What’s Next?

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Brace Hemmelgarn-USA TODAY Sports

It’s still too early to judge Portland’s return for Lillard since the ultimate result of this trade is still to be determined. They should be able to extract a solid haul for Holiday, which could include one or two first-round picks. However, if extracting the most assets possible was imperative, it was too late for that.

Lillard trade rumors began as early as 2021, shortly after they were eliminated in the first-round by the Denver Nuggets in six games. While no trade request culminated, it was apparent that their window with their core at the time was closing. They were limited in ways to significantly improve the roster and were facing a perpetual tax crunch with so many key players due for raises. They kept Lillard for two years and even rewarded him with a two-year extension last summer, projected at $120 million.

While the four years, $216 million remaining on the 33-year-old can be viewed as an impediment, it’s more likely the overall trade market finally cooled down. Since the Anthony Davis and Paul George trades to Los Angeles in 2019, through the Kevin Durant trade to Phoenix seven months ago, teams have paid massive premiums for star players. These packages often included massive control of their draft over the next seven years on top of valuable prospects.

Perhaps a lot of potentially interested teams ran out of assets long ago by participating in the trade market in seasons past. But it’s also likely that the new CBA and the implementation of the second tax apron could be making teams more conservative with their draft equity. Teams that go over the second tax apron are essentially limited to increasing salary through re-signing their own players, draft picks, and minimum salaries.

This isn’t to say that the Blazers are in a bad spot. When things weren’t looking great on the court in the last two seasons, they bottomed out and got two high lottery picks. Their backcourt of the future looks set with Scoot Henderson, Shaedon Sharpe, and Anfernee Simons. They’re a couple of frontcourt prospects away from being on a promising path back to the playoffs. But in fairness, they probably could’ve gotten a haul for Lillard had they moved him anytime before this offseason.