Can the Trail Blazers appease Damian Lillard? The pressure is on as NBA free agency begins: Analysis

In the next episode of “As the Portland Trail Blazers Turn …” (cue strings).

Will Damian Lillard stay loyal to the Blazers? Do the Blazers remain worthy of his love? Should general manager Joe Cronin make a big trade to help Lillard? If he doesn’t, will Lillard file for divorce? Is rookie Scoot Henderson ready to take the throne? Could Anfernee Simons be traded?

And on and on and on.

The drama unfolding between Lillard and Trail Blazers management has reached such soap opera levels that Daytime Emmy Award nominations might be in order.

But things are coming to a head one way or another. Free agency begins Friday, and after the Blazers failed to complete a major trade during Thursday’s draft, the pressure is on to come up with a big move to appease Lillard or risk him seeking a trade.

This situation has been two years in the making. Lillard, who has been loyal to the Blazers throughout his 11-year career, made it clear he wants to see a way to win. Still, the Blazers have made small inroads toward that goal. After two terrible seasons, they ended up keeping two lottery picks instead of using the draft capital to complete a trade, leaving Lillard frustrated and at least looking at other options.

Lillard and his agent, Aaron Goodwin, met with Cronin on Monday. Cronin issued a statement saying he remains committed to building around Lillard. NBA sources tell The Oregonian/OregonLive that the meeting went well, but the situation remains the same.

Improve the roster or Lillard may ask out.


Cronin made it clear the day he took over for Neil Olshey in 2021 that he planned to build a contender around Lillard.

Two trade deadlines, two tank jobs, two drafts and nearly two summers later, the Blazers look nothing like a contender.

Lillard, 31 when Cronin took over, is now approaching 33, creating a greater sense of urgency to advance the stated agenda.

Scoot Henderson arrives at the Barclays Center before the NBA basketball draft, Thursday, June 22, 2023, in New York. (AP Photo/John Minchillo)

Nevertheless, Cronin’s decision to keep No. 3 pick and select Henderson was the right move.

Cronin made it clear he valued taking the best player over the best positional fit. That dispelled any concerns that Henderson was a 6-2 point guard, the last thing the Blazers needed.

It also made sense for Cronin to walk away from what he called underwhelming trade offers. The No. 3 pick received some interest, but not the type you’d expect with what many called a “generational talent” on the board.

Were other teams simply not that high on Henderson? Did Lillard declare that a failure on the part of the Blazers to upgrade the roster could lead to a conversation about his future impact teams to sense desperation and try to fire Cronin? Perhaps Lillard’s talk of liking Miami or Brooklyn as landing spots did the Blazers no good in trade discussions.

Whatever the reasons, the offers for the No. 3 pick failed to blow Cronin away, so he made what he believed to be the smartest move for the franchise, and that was to select and keep Henderson.

But the move didn’t address the team’s pressing needs, leaving Lillard unsatisfied.


The hype around Henderson is thick. But is it too much?

Henderson has an NBA body, strength, high-end athleticism, strong basketball instincts, is unselfish, a gifted passer and dribbler and can attack the basket with a ferocity that the Blazers need.

But he is 19.

The absolute last thing the Blazers needed to win now was a 19-year-old, 6-2 point guard playing behind their 33-year-old point guard while also seeing time at shooting guard.

What the Blazers needed was a proven NBA veteran with either an All-Star past or All-Star potential, preferably 6-6, who could ideally play either small forward or center.

FILE – NBA G League Ignites Scoot Henderson dunks against the Boulogne-Levallois Metropolitans 92 in the first half of an exhibition basketball game on Oct. 4, 2022, in Henderson, Nev. Henderson is among the top guards in the upcoming NBA draft. (AP Photo/John Locher, File)

Adding Henderson instead is simply not a recipe for success. Not at the level Lillard wants.

The only player to operate at an all-star level for a championship team under the age of 21 was the 6-9 Magic Johnson in the 1979-80 season while playing with center Kareem Abdul-Jabbar. Johnson turned 20 during his rookie season.

6-6 Kobe Bryant, in his fourth season with the Lakers, won a championship in 2000 while playing with Shaquille O’Neal at age 21.

But Henderson isn’t the 6-6 Bryant or the 6-9 Johnson. And Henderson isn’t playing with Abdul-Jabbar or O’Neal. He plays with another 6-2 point guard as the team’s superstar.

It’s not impossible for Henderson and Lillard to succeed as a backcourt duo, but it’s highly unlikely. Especially considering Henderson has never played at an NBA championship level in his life.

Not even with G League Ignite. Last season, Henderson averaged 17.6 points, 6.4 assists and 5.8 rebounds while demonstrating his clear all-around potential. However, he also made 3.5 turnovers per game while shooting a relatively lackluster 42% from the field and 27.5% on three-pointers. Nine times in 19 games he shot below 40% from the field.

For all the talk about Henderson’s defense, he posted a 118.4 defensive rating with a 115.9 offensive rating, leaving him with a negative rating of minus-2.5.

To be fair, stats and ratings can be influenced by those around you. He will definitely play with better players on the Blazers.

Still, Henderson will need to improve dramatically over the summer to surpass the level of play Anfernee Simons showed last season at shooting guard and Shaedon Sharpe late in the season when he ran the show.

Is it plausible in year 1, or even year 2?

So therein lies the problem. If Henderson is just going to be good as a rookie, then the Blazers wouldn’t expect to be better than they were last season, and especially than they would have been had they traded Henderson for a proven All-Star.

And if so, what is there for Lillard to be excited about?


If Lillard is serious about winning a championship, he should absolutely request a trade if the Blazers fail to upgrade the lineup.

Cronin has said he has no intention of trading Lillard. And that could be true. But that could also change in a heartbeat if Lillard declares he’s done in Portland.

Portland Trail Blazers guard Damian Lillard speaks to the media during exit interviews at the Moda Center in Portland, Oregon on Sunday, April 9, 2023.

Lillard is at the age where it makes no sense to keep waiting for a miracle. He had arguably the best season of his career last season, and it was wasted because when injuries hit the team, the Blazers only had undrafted younger players to fill in.

Cronin blamed himself for not having more veterans on the team. Billups said the Blazers absolutely needed more veteran depth and length. Lillard echoed their sentiments.

So why stick around to see how Henderson and Sharpe develop when odds are they won’t be ready to make a real impact in winning for another two or three seasons?

The Blazers could reject a Lillard trade request, but doing so could be dangerous. If the goal is to wait to see how the season goes and maybe make a trade at the trade deadline, then so be it. But if Cronin were to stick with Lillard because he doesn’t think a suitable deal is out there, that could backfire.

Lillard, the consummate professional, would probably still give 100%. But he could also feel slighted. After years of remaining loyal to Portland, he could feel a sense of disloyalty represented by not trading him to a contender after failing to build a better roster around him.

Plus, what would keeping Lillard accomplish for Portland? The Blazers would certainly be better with Lillard than without. But what is the end game here? Would it be better to reach the playoffs as a low seed and be eliminated in the first round with Lillard, or to trade him for assets and in the process ensure the Blazers would return to the lottery in 2024?

Making the playoffs in 2024 would mean surrendering the team’s first-round pick to the Chicago Bulls. Returning to the lottery could provide an opportunity to draft a starting forward or center.

If the Blazers accumulated three first-round picks by trading Lillard and also returned to the lottery next season, they would have eight first-round picks through the 2029 NBA draft.

Keep Lillard and the Blazers would only have five first-round picks through 2029 and likely no picks at all in 2024.

Then there is the eventual public relations fallout. Lillard is a talker. The Blazers don’t want to have a negative Lillard in the locker room, upset that he’s being forced to play in a bad situation. And what would he say to other NBA stars about the NBA franchise refusing to trade him to a better situation like the franchise did with Clyde Drexler in 1994?

The Blazers were no longer contenders, and they sent Drexler to Houston, where he won a championship with Hakeem Olajuwon.

Damian Lillard (0) of the Portland Trail Blazers drives past Caleb Martin (16) of the Miami Heat during the second quarter at FTX Arena on November 7, 2022 in Miami. (Photo by Megan Briggs/Getty Images)

The Blazers have had enough trouble luring free agents and trade targets to Portland. Doing so after preventing Lillard’s chance to win elsewhere after he sacrificed prime years to give the Blazers a chance to win with him wouldn’t make the Blazers more attractive.

For all the love being shown to Henderson and Sharpe, let’s not forget that there’s no guarantee either would stay in Portland long-term. It is likely that they will sign their first extension. But after that, when each is still in their mid-20s, their attitude toward the franchise could influence their decision to stay or leave.

And that feeling could be influenced by how they saw Lillard being treated after everything he did for the franchise.


The Blazers have one last chance to get this right. They could still move Simons and/or Jusuf Nurkic to acquire a much-needed small forward.

Toronto’s OG Anunoby would still be in play. Acquiring him could upgrade the defense tremendously.

Cronin could also free up future draft picks by siding with the Bulls, who are owed a future first-round pick. That pick is lottery protected, which is why the Blazers kept it this year. Tell that pick in 2024, and the Blazers would then be able to trade first-round picks in 2026, 2028 and 2030.

Portland will also have a mid-level exception worth $12.2 million and a semi-annual exception worth $4.4 million. The Blazers also have trade exceptions worth $8.3 million and $2.6 million, which could allow the team to take back more player salary in a trade than it sends out.

But the Blazers better move quickly to please Lillard. Taking too long to complete a major deal would cause other options to dry up, hindering the Blazers’ chances of landing valuable additional veterans.

If all efforts fail, the Blazers’ next trade could be to ship Lillard to a desired destination. It would end what has been a brilliant career from an individual standpoint for the seven-time All-Star, but also leave his Blazers tenure filled with “what-ifs.”

— Aaron Fentress | [email protected] | @AaronJFentress (Twitter), @AaronJFentress (Instagram), @AaronFentress (Facebook). Subscribe to Oregonian/OregonLive newsletters and podcasts

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