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Trail Blazers Crushed Damian Lillard Deal

Nobody thought Portland would do this well when backed into a corner.

Milwaukee Bucks Media Day Photo by Stacy Revere/Getty Images

The Portland Trail Blazers trading Damian Lillard to the Milwaukee Bucks last week was the biggest event to hit the franchise since All-Star forward LaMarcus Aldridge left in free agency way back in 2015. Like the Aldridge Saga, Lillard’s exit was drawn out over the course of months, with speculation, rumor, and angst replacing hard into. Lillard’s departure brought far more back to the franchise than Aldridge’s did, however. That, at least, is something to be thankful for.

The Blazer’s Edge Mailbag is stuffed to overflowing with questions about various permutations of the deal. Let’s address them today, at least in an overall sense.

Losing a player who defined a generation is never easy. It’s not often lucrative either. When Bill Walton left for the San Diego Clippers in 1979, Portland received forward Kermit Washington, center Kevin Kunnert, and a 1980 first-round draft pick in compensation. Trading Clyde Drexler to the Houston Rockets in 1995 got Portland forward Otis Thorpe, prospect Marcelo Nicola, and a 1995 first-round pick. Rasheed Wallace netted a relatively large return from the Atlanta Hawks in 2004: forward Shareef Abdur-Rahim, center Theo Ratliff, and guard Dan Dickau. Aldridge got Portland nothing but future cap space.

Getting Deandre Ayton, Jrue Holiday. an unprotected 2029 first-round pick, and pick swaps in 2028 and 2030 for Lillard (plus Jusuf Nurkic, Nassir Little, and Keon Johnson) already made the deal the best superstar trade the Blazers have ever made. Holiday is an active All-Star, Ayton isn’t terribly far off.

The Blazers didn’t keep Holiday, of course, but moving him for an unprotected 2029 pick from the Boston Celtics, a modest first-rounder originally from the Golden State Warriors, Malcolm Brogdon, and Robert Williams III sweetens the pot for a team looking to rebuild.

The Blazers now have two unprotected 2029 picks, a 2024 pick protected for slots 1-4, two pick swaps, a talented young center, and two serviceable veterans, one of which may be moved for another modest first-rounder.

让我们再说一遍。开拓者有潜在的圣ar center who was picked first overall in 2018, the potential for two future lottery picks outright, two more swaps for same, plus a first-rounder and two more mid-level players for a guy they drafted sixth overall in 2012 and got the best 11 years of his career out of.

Would it have been nice to keep Damian Lillard for his entire career? Yes.

Is that haul pretty nice? Also yes. I’d do that all day long.

Portland success in the trade market speaks to the character and value of Lillard and Holiday. It also speaks to General Manager Joe Cronin’s shrewdness in leveraging same. The stairstep approach he employed, flipping Holiday and possibly Brogdon, was particularly smart. The original goal for a Lillard trade—before anybody found out about preferred destinations and such—was a young potential star and lots of draft picks. That’s exactly what Portland nabbed. They just had to go through a couple extra steps to get there.

For the next few years, the Blazers will focus on developing the talent they already have: Ayton, Scoot Henderson, maybe Shaedon Sharpe. They’ll have to make decisions on veteran forward Jerami Grant and young guard Anfernee Simons. Either could be spun for more picks, potentially between now and 2028, when the Lillard bounty matures.

If their current crop of players develops, the Blazers should be in for a heck of a boost from those future picks as the decade comes to a close. If nobody from the present generation comes through, they are already primed for their next rebuild.

Winning now is always the best solution in the NBA. Realistically, that wasn’t going to happen in Portland even if Damian Lillard returned. If they had to settle for the next best choice, starting fresh with the pump already primed and stockpiling future picks was a good alternative.

One of the interesting things about the series of deals surrounding Damian Lillard was how happy all the franchises seemed to be with their return. Milwaukee coveted Dame. Boston was ecstatic with Holiday. Phoenix liked their increased depth behind their new Big Three.

The Blazers should be equally happy with the haul they netted. Lillard for Ayton alone would have been a better deal than anything Miami was offering, at least in terms of headline players. Three picks, two swaps, and two players on top made the swap inarguable.

We can make an argument for any team in the orbit of these trades falling short. Lillard might age out or not fit with the Bucks. Holiday is safer with the Celtics, but he still has to match with Jayson Tatum and Jaylen Brown. I’m not sure Phoenix actually got better by losing Ayton. Their strategy was situational.

Portland’s approach may also fail, ultimately, especially if the picks turn out to be modest and the swaps non-functional. But the Blazers have taken as good of a swing as any of the other teams involved. Given where they started from, stuck in a vise created by Lillard’s narrow trade request, this was more than anybody could ask for.

Thanks for ALL your questions to the Mailbag! You can send them to blazersub@gmail.com and we’ll try to answer as many as possible!