The Portland Trail Blazers should preempt Damian Lillard’s trade request

With Damian Lillard reconsidering his long-term future in Portland, the Trail Blazers should preempt his inevitable trade request this offseason.

After years of pledging his loyalty to the Portland Trail Blazers, Damian Lillard suddenly appears less certain about his long-term future than ever. He’s made clear that the status quo is no longer acceptable, which could force the Blazers into making win-now upgrades in a last-ditch effort to appease him.

Before they go down that road, the Blazers should take a step back and be brutally honest with themselves. If they don’t have a realistic way to vault themselves into championship contention, this offseason may be their best opportunity to trade Lillard and embark upon a hard reset.

It might be time for the Trail Blazers to trade Damian Lillard, before things get worse

After a surprise run to the Western Conference Finals in 2019, the Blazers have bowed out in the first round in each of the past two seasons. Their loss to the injury-ravaged Denver Nuggets this postseason was seemingly the straw that broke the camel’s back for Lillard.

“Our environment has always been great,” he recently told Yahoo Sports’ Chris Haynes. We’re not losing a lot, but we were eliminated by a shorthanded Denver team that I felt we should have beat. I just walked away from that really disappointed. I was like, ‘Man, this just isn’t going to work.’”

The Blazers are now facing a fork in the road with their current roster.

They could talk themselves into re-signing Norman Powell in free agency and running back the same core. The five-man lineup of Lillard, CJ McCollum, Powell, Robert Covington and Jusuf Nurkic was a plus-14.2 in 784 possessions last season, which ranked in the 78th percentile league-wide, according to Cleaning the Glass.

However, there isn’t much depth behind that group. Derrick Jones Jr. faded out of the Blazers’ rotation as the season progressed, while Anfernee Simons, Nassir Little and CJ Elleby are the only young prospects under contract in Portland. The Blazers don’t have either a first- or second-round pick in this year’s draft, either.

With the pipeline of young talent running dry and the luxury tax looming, there’s only so much retooling that the Blazers can do around Lillard. There’s no guarantee that a major roster overhaul would stave off a trade request for long, either.

Trading Lillard this offseason thus appears to be wiser from a long-term team-building perspective.

Covington, Nurkic and Jones are all heading into the final year of their respective contracts. Unless they agree to extensions in the coming months, they’ll all become unrestricted free agents next offseason. That puts the Blazers in a tricky spot.

By staying in win-now mode and keeping Covington, Nurkic and/or Jones on the roster, the Blazers would run the risk of losing them for nothing next summer in free agency. They could instead attempt to flip them at the trade deadline—particularly if Lillard asks out by then—but they’d otherwise have to toe the line between attempting to stay competitive now and keeping an eye on their long-term future.

The Blazers could instead pivot into a rebuild this offseason with a Lillard trade and begin shipping out their other vets, too. They aren’t likely to recoup the two first-round picks they gave up for Covington last offseason, but they shouldn’t have trouble generating interest in either him or Nurkic on the trade market. Whatever they could add to their war chest would beat seeing them walk as free agents next summer.

Portland also needs to consider the leaguewide trade landscape while weighing how to approach this offseason.

As Bleacher Report’s Jake Fischer first reported over the weekend, Bradley Beal appears to be reconsidering his future with the Washington Wizards, much like Lillard is with the Blazers. The Wizards “don’t want to shop him, and he hasn’t asked them to do so,” according to Fred Katz of The Athletic, but Beal “at times has been very much on the fence about whether or not he wants to remain with the Wizards,” according to Shams Charania of The Athletic.

The Blazers and Wizards may thus be engaged in a game of chicken with one another and their respective stars. Whichever one signals a willingness to move Lillard or Beal first may have a leg up on the best trade packages, particularly if it happens between now and the start of the 2021 NBA draft on Thursday.

For now, there’s clarity as to which teams own which picks and which prospects might still be on the board at those spots. Once the draft comes and goes, any picks-centric package will be riddled with far more uncertainty.

The Blazers might prefer a package featuring an All-Star such as Ben Simmons or Pascal Siakam rather than a full-scale teardown. If the Wizards feel the same way, they could snipe the best available package by trading Beal before Portland caves on Lillard.

Some of those trade packages might lose their value after the next few days, too. The Golden State Warriors can offer Nos. 7 and 14 picks in this year’s draft along with James Wiseman and Andrew Wiggins (for salary-matching purposes), but those picks may become less enticing once they turn into actual prospects. The Toronto Raptors figure to take either Jalen Suggs or Scottie Barnes at No. 4., but what if Portland or Washington prefer the prospect whom they don’t select?

The Blazers don’t appear likely to trade Lillard before Thursday’s draft, particularly since he’s currently over in Tokyo with Team USA. But based on the recent reporting from TrueHoop’s Henry Abbott, Lillard does not seem long for Portland.

“Sources say he told his national team friends that he thought the situation in Portland was getting worse,” Abbott wrote about Lillard. “The next day was his birthday; he would turn 31. He told the group that he had meetings with his team coming up the day after that, and he was thinking about demanding a trade.”

Lillard has yet to issue that trade demand, but it appears to be only a matter of time before he does. Rather than wait for him to force their hand, the Blazers should recognize the opportunity they have in front of them this offseason to hit reset on their roster and begin building anew.

If they wait out Lillard for one more year and lose Covington, Nurkic and/or Jones in free agency next summer for nothing, they’ll only be hurting themselves more in the long run. The same goes for the Wizards beating them to the punch by trading Beal for a blockbuster package.

Trading one of the best players in franchise history is not a decision to be taken lightly. But considering the state of their roster, the Blazers should realize this offseason may be their best chance to turn the page and recoup as much value as possible.