Damian Lillard putting Portland Trail Blazers in no-win situation

Damian Lillard’s waffling about his future leaves the Portland Trail Blazers with no good options this offseason.

On Friday, Damian Lillard did everything but request a trade from the Portland Trail Blazers.

In an interview with Chris Haynes of Yahoo Sports, Lillard made it clear that he’s no longer content with the status quo in Portland.

“I think that’s the stage we’re at as a team where we all, not just me, not just my teammates, not just our new coaching staff, the front office, everybody in this organization must look in the mirror because we’ve constantly come up short,” Lillard said. “We have to look in the mirror and say I have to be better because whatever it is we’re doing is not working and it’s not giving us the shot to compete on the level that we want to compete on.”

While speaking with reporters following Team USA practice later that day, Lillard said he expected to remain with the Blazers next season. However, he sounded less certain about his long-term future in Portland than he ever had before.

“Right now I’m not sure what I’m going to do. What I can say is my intentions and my heart has always been set on being in a Trail Blazers uniform for my entire career,” Lillard said. “But I think over time, you want to win it all. And I want to win it all in a Trail Blazers uniform. But we all have to be making strides toward that.”

In other words, “run it back” is no longer a viable strategy.

How can the Portland Trail Blazers satisfy Damian Lillard?

The Blazers will need to undergo seismic roster changes this offseason to keep Lillard satisfied and stave off his seemingly imminent trade request. But in pivoting even harder into win-now mode, they may wind up doing more damage to their long-term future than they would if they just trade Lillard now.

There’s no better example of that than Norman Powell.

Ahead of the March trade deadline, the Blazers shipped Gary Trent Jr. and Rodney Hood to the Toronto Raptors in exchange for Powell, who was having a career year.  He wound up averaging 17.0 points on 44.3 percent shooting in 27 regular-season games with the Raptors following the trade, and he’s now poised to cash in as an unrestricted free agent.

ProFitX estimates Powell’s production to be worth $22.8 million next season and $68.3 million over the next three years, which is likely in line with the contract he’ll wind up signing this offseason. He isn’t a max-caliber player, but some team is bound to offer him around $20 million annually if the Blazers don’t.

Powell’s scoring and shooting ability will help to justify that cost, although he doesn’t bring much else to the table. He can create for himself off the dribble, but he isn’t a great playmaker for others, and he isn’t a lockdown defensive wing by any means, either.

By trading for Powell only months ahead of his foray into free agency, the Blazers backed themselves into a corner. They can exceed the salary cap to re-sign him because they have his Bird rights, but they won’t have cap space to find a suitable replacement if he walks.

In other words, the Blazers might have to overpay Powell to ensure they don’t further infuriate Lillard by losing him for nothing. But if Lillard later asks out, they might have no easy way out of Powell’s bloated contract.

The Blazers also need to decide what to do about Zach Collins, whom they traded up to acquire on the night of the 2017 NBA draft. Injuries limited the big man to only 11 games in 2019-20 and cost him the entire 2020-21 season, which makes it difficult to bank on him as an impact contributor moving forward.

Collins could be a restricted free agent this summer rather than unrestricted, but Portland does not plan to tender his $7 million qualifying offer, according to Jason Quick of The Athletic. He’s currently on the mend from yet another ankle surgery and might not be available for the start of the 2021-22 season.

The Blazers will still have Bird rights on Collins even if they don’t extend him a qualifying offer, so they could attempt to bring him back at a lower price. But given his timetable to return (4-6 months), their proximity to the luxury tax and Lillard’s win-now mandate, they may decide they can no longer wait on the 23-year-old to get and stay healthy.

And if the Blazers do attempt to overhaul Lillard’s supporting cast via trades, they’ll have to balance the short and long term. While they may want to prioritize their immediate future to keep Lillard happy, they should also form a contingency plan in case he does eventually request a trade.

The Blazers have already traded away their first-round pick this year and four of their next five second-rounders. Given the uncertainty surrounding Lillard’s future, they should be highly reluctant to part with additional first-round picks in any trade unless they’re heavily protected. Trading multiple future firsts should be a non-starter if they aren’t acquiring a young star whom they can build around if Lillard winds up leaving.

The Blazers will likely receive an unprecedented haul for Lillard if (when?) they do begin entertaining trade offers. Trades for Paul George, Anthony Davis and James Harden set the bar high in recent years. They should expect multiple future first-rounders along with high-upside young prospects at a bare minimum. That can be the foundation of their future.

Until then, they’ll need to plan with the post-Lillard era in mind. Lillard’s win-now mandate will make that nearly impossible, though.

How the Blazers balance those two competing interests this offseason may wind up determining their trajectory over the next half-decade.

Unless otherwise noted, all stats via NBA.com, PBPStats, Cleaning the Glass or Basketball-Reference. All salary information via Spotrac.

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