The Damian Lillard saga is the story of the 2021 NBA offseason. Will he stay in Portland, hoping the Trail Blazers can finally build a championship contender around him, or will he request a trade to give himself a better shot at reaching the NBA summit?
To this point, Lillard has publicly denied he's planning to ask out, at least for the moment. But the Blazers can't take his loyalty for granted.
"I don't think he wants to leave. He has built an empire here," a Blazers executive told Jason Quick of The Athletic. "But we have to assume he is leaving to make sure he is not leaving."
Lillard's request of Portland is simple—he wants an improved roster around him.
"I think if you look at our team as it is, going into next season, I don't see how you can say this is a championship team," he told reporters last week. "We're in the playoffs every year. We've got a great environment, great city, we have great fans. There's a lot of positives, but I just think we've reached that point where it's like, 'OK, but it's not enough. Do we actually want to win it all? Is that what we are shooting for?' And we've got to do things to show that. We've got to put action behind that desire to win at that level. That's been my only thing this entire time."
As Quick noted, "Lillard’s call for accountability and action has been met with the appropriate alarm." No surprises there. But actually improving the roster is where things get more complicated.
The fastest route to improvement would be adding a true second star. CJ McCollum is a very good player, but he's not good enough to be the second star on a championship team, not when you compare Lillard-McCollum to some of the other star pairings in the NBA.
Perhaps the Blazers could build a trade around McCollum, future picks (they don't currently have any selections in the 2021 draft) and young players like Anfernee Simons, Nassir Little or CJ Elleby. The question is, which stars are going to be available via trade?
The Philadelphia 76ers seem very, very unlikely to do the widely proposed McCollum for Ben Simmons swap if there's any chance that Lillard will eventually request a trade. Why trade your best asset for a player like McCollum—who may be a better fit next to Joel Embiid but won't significantly improve your championship odds—and kill any chance at getting Lillard in the process?
Bradley Beal is always suggested as a star who could eventually be dealt, but neither he or the Washington Wizards have given any indication that will happen anytime soon, and even if it did, plenty of other teams could beat Portland's best offer.
There also aren't any franchise-altering players in free agency the Blazers are going to get with $115.5 million in salary cap allocations already for the 2021-22 season, per Spotrac.com, putting them over the $112.4 million salary cap already. And that's before potentially re-signing Norman Powell, who won't come cheap.
Perhaps a McCollum sign-and-trade for a player like Kyle Lowry or DeMar DeRozan, if either is inclined to go to Portland, could happen. But again, does such a deal really improve Portland enough to compete with teams like the Brooklyn Nets, Milwaukee Bucks, either Los Angeles team (assuming Kawhi Leonard returns to the Clippers and plays at some point next season), the Denver Nuggets or Phoenix Suns (if Chris Paul returns)?
For the Blazers to truly, markedly improve—and not just get slightly better around the margins—Neil Olshey is going to have to pull a rabbit out of his hat. And that's why the Lillard buzz isn't going to die down anytime soon. If Dame truly wants to compete for titles, chances are he's eventually going to have to request that trade.