Damian Lillard’s determination to play for the Miami Heat places Trail Blazers in a bind: Analysis

The Damian Lillard situation has already moved far beyond being a simple NBA trade negotiation with one team seeking to trade assets to another for a superstar.

Lillard, the Portland Trail Blazers and the Miami Heat are locked in a battle of wills with each showing no signs of budging.

The face of the Blazers franchise, and arguably its greatest player ever, has shelved his once highly-praised loyalty to seek a trade specifically to the Heat, to the point where attempts to trade him elsewhere could lead to an extremely contentious situation.

The Blazers, of course, seek maximum value for their unhappy superstar, and general manager Joe Cronin has been canvassing the NBA for offers.

Then there’s Miami, dangling an initial offer that lacks the pop one would consider worthy of a player of Lillard’s caliber.

Who will blink first?

Tough to say. But for now, the only certain truth appears to be that the Blazers and Heat will either ultimately work together to find an amicable solution or major trouble could follow.

Lillard did not merely request a trade. He demanded one to Miami, according to sources.

Lillard isn’t seeking to leave the Blazers simply to play elsewhere. He is leaving the Blazers because he has come to the realization that a realistic chance of winning a championship in Portland doesn’t exist.

With Miami, fresh off of losing in the NBA Finals to Denver, Lillard would have the best team around him he has ever enjoyed.

This was an agonizing decision for the seven-time All-Star, who has remained in Portland for 11 years while many other stars around the league have changed teams numerous times while in search of elevated opportunities to win a championship.

NBA sources have told The Oregonian/OregonLive that Lillard remains pained over the situation. He preferred to see the Blazers add at least a couple of good veteran players who could help. He didn’t even require a superstar, just signs that the team was moving in the right direction.

The roster, as it stands following the draft and the start of free agency, simply isn’t good enough from Lillard’s perspective.

On draft night, the Blazers considered offers for the No. 3 pick, but they weren’t strong enough to convince Cronin to pass on selecting point guard Scoot Henderson, whom Cronin called, “transcendent.”

By that point, Cronin, according to sources, had already deemed Shaedon Sharpe, last year’s lottery pick, to be virtually untradeable.

According to sources, deals were offered that would have improved the team enough to please Lillard. But rightly or wrongly, Cronin made the decision to hold on to young assets rather than flip them for veteran talent.

And that’s Cronin’s prerogative as general manager. His decisions don’t lack merit. Some offers, according to sources, would have required sending the No. 3 pick, Sharpe, Anfernee Simons and Jusuf Nurkic for one star.

Worth it to Lillard? Maybe. For the Blazers? Not if Henderson and Sharpe develop into what Cronin believes they could be.

But that direction, sound or otherwise, is not for Lillard, who clearly stated during exit interviews in April that he didn’t want to see the addition of more long talent. He wanted needle movers to help the Blazers contend now.

Ultimately, Lillard gave Cronin 18 months to build the contender around him that the general manager said he felt obligated to construct. Not two or three years.

So, the logical result for both parties is for the Blazers to trade Lillard.

Here is where things become tricky.

Do the Blazers owe it to Lillard to fulfill his very specific request? Or, should they seek to trade him to the highest bidder?

Lillard, who turns 33 on July 15, definitely doesn’t want to go from one mediocre team to another. If his only choices were to lose with Portland or lose with another mediocre team, he would choose to remain with the Blazers.

Lillard wants to win. And he doesn’t want to do so on speculation. He wants to go where he has an obvious chance to take advantage of the final few years of his prime and contend for a championship.

Philadelphia, Boston and Brooklyn would also be strong landing spots for Lillard, but a source says that he has no interest in playing for any of those teams.

Lillard, who last summer signed a two-year, $112 million extension, now has roughly $216 million over four years remaining on his contract.

Some have argued that if Lillard wasn’t committed to living up to his contract, then he shouldn’t have signed it. But that works both ways. Lillard signed the contract after being told repeatedly that the franchise’s goal was to be aggressive in building a contender around him.

Lillard made his goals clear in the summer of 2021, when for the first time his loyalty to the franchise began to show cracks. He stated that his future in Portland could be in doubt if the Blazers, then led by president of basketball operations Neil Olshey, failed to demonstrate that they were serious about winning.

Lillard remained but core muscle surgery during the season caused him to miss 53 games. Olshey, fired in November 2021, was replaced by Cronin. Lillard decided to give the first-time general manager a shot to pull off his stated goal.

But Lillard never said he would give Cronin four years, or even two. Cronin himself said in 2022 that his plan ran through 2023. Not 2024 or 2025.

Lillard also made it clear following the end of this season that he didn’t want to see more youth added to the roster. The Blazers’ clearly stated goal was to acquire a veteran talent and do so by potentially trading the No. 3 pick.

Instead, Cronin used three draft picks (No. 3, No. 23 and No. 43) to add three rookies, including Lillard’s future replacement at point guard.

So, in 18 months, the only major move made to help Lillard win was the crafty move of essentially turning the 6-foot-3 CJ McCollum into Jerami Grant and Josh Hart, who at the 2022 trade deadline was dealt to New York for the No. 23 pick and Cam Reddish, now with the Lakers.

Even re-signing Grant didn’t sway Lillard because he was on the team last season. The Blazers needed at least another Grant-level player, or two.

Yet Lillard, following the draft, was left with three more young players, exactly what he didn’t want to see.

On June 26, a frustrated Lillard and his agent met with Cronin. After the chat, Cronin released a statement saying they had a good meeting and the team remained committed to building around Lillard.

However, sources say that all the meeting did was buy time until free agency. Lillard, still desperate to stay in Portland, gave Cronin one last opportunity to make some deals.

During his post-draft news conference, Cronin said that the seeds of future deals had been planted during talks leading up to the draft.

Yet amid a flurry of NBA activity during Friday’s start of free agency, the Blazers did nothing other than reach an agreement with Grant on a new deal.

A dejected Lillard had seen enough. In his view, the Blazers weren’t serious about achieving their stated obligation to him. He didn’t expect the Blazers to make a bad trade, according to sources. But in the end, why the Blazers went young doesn’t matter to Lillard. The end result is that the Blazers might have solidified a strong future but they did little to impact the present.

If the Blazers weren’t nudging Lillard out the door, it sure seemed that way, sources say.

Sending Lillard to another team without his consent could lead to a standoff. But that doesn’t mean Miami has all the leverage.

The reported offer from the Heat to Portland for Lillard is light. Promising young guard Tyler Herro, 23, Duncan Robinson (salary filler) and two first-round picks won’t cut it, and rightfully so.

Lillard’s value is far greater, and according to sources, the Blazers have little interest in acquiring Herro, who plays the same position as Sharpe and is owed $120 million over the next four seasons.

Therefore, while the Blazers might ultimately be forced to deal with Miami, they shouldn’t succumb to being fleeced.

The Blazers, according to sources, our after a major big haul of assets for Lillard. A deal in the ballpark of what Brooklyn received for Kevin Durant, or what Utah received from Minnesota for Rudy Gobert, and from Cleveland for Donovan Mitchell.

Each deal involved three to four first-round picks and solid to good players.

Such a deal with Miami will require the help of a third team. Also, the Heat can free up another first-round pick by working out a deal with Oklahoma City, which is owed Miami’s 2023 first-round pick that is top-14 protected.

Conveying that pick impacts what future picks the Heat can trade to Portland.

Through creative negotiating, an NBA source said that the Blazers should be able to net four first-round picks and players with manageable contracts, maybe even a young star that fits better than Herro, if they play their hand correctly.

Where everything could become problematic is if the Blazers seek out a trade package from a team not based in South Beach.

Chris Haynes of Bleacher Report reported Monday that Boston, the LA Clippers, Minnesota and New Orleans have inquired about obtaining Lillard.

Moving Lillard elsewhere, however, would require persuasion since Lillard has made his intentions for playing in Miami clear.

And if such an ask fails, moving forward with a trade could create a problem.

Lillard lacks a no-trade clause, so the Blazers could complete a trade with another team against his wishes. But the likelihood of that happening isn’t very good.

Any team that negotiates with the Blazers would likely be hesitant to invest the type of assets Portland seeks and commit to paying $216 million over four seasons to a star with massive clout who doesn’t want to play for that team.

Undoubtedly, an interested team would reach out to Lillard and his representation to let them know that they had engaged in negotiations.

At this point, according to NBA sources, Lillard would tell that team not to trade for him.

The interested general manager must then decide if he wants to commit a superstar’s worth of assets that they can’t get back (no returns) for a player who literally said he doesn’t want to play for that team.

Also, Lillard would view being forced to play where he doesn’t want to be as a sign of disrespect.

Some have suggested that an interested team should go ahead with the deal because Lillard would show up in order to get paid.

Lillard’s professionalism, competitiveness and pride in his game would likely prevent him from mailing it in. But then that team is potentially getting a player who is only there to collect a paycheck.

That’s not a recipe for team success.

Another option for Lillard could be to simply not report to his new team. This would be a dramatic move and cost Lillard millions, but he has already made well more than $300 million in player salaries and endorsements. He isn’t hurting for a paycheck.

Such a threat could give a team pause.

But why would or should this situation become so volatile? Superstars typically dictate where they end up. Lillard is a superstar.

Lillard’s career in Portland is over barring a standoff that leads to the All-NBA guard remaining on the roster when training camp rolls around in September.

What a disaster that would turn out to be. The last thing the franchise and Lillard should want is a nasty split. Even if Lillard finishes his career elsewhere, he plans to reside in the Portland area when his playing days are over. Construction of a new home is near completion.

Former Blazers greats Clyde Drexler and Bill Walton live elsewhere and rarely show up in Portland for games.

Lillard has talked about spending a lot of time at the Moda Center, attending games and hanging around long after he launches his final deep three-pointer while in a Blazers uniform.

So it’s best for everyone involved that this increasingly volatile situation concludes with a soft landing.

Lillard wants to win a title. The Heat want that to happen in Miami. The Blazers want a fair package of assets.

The NBA’s summer league starts Friday in Las Vegas. Cronin will have opportunities to meet face-to-face with rival general managers to discuss options.

But in the end, Lillard holds the trump card. He doesn’t have to agree to play where he doesn’t want to.

Unless he changes his stance and accepts a trade elsewhere, this could become messy if the Blazers attempt to force his hand.

However, getting a legitimate contender like Boston involved in bidding for Lillard, even if he doesn’t want to play there, could at least make Miami blink and nudge the Heat to up their reported offer.

Miami has positioned itself to acquire Lillard and their two stars, Bam Adebayo and Jimmy Butler, want their good friend with them in Miami.

That’s also what Lillard wants. And all signs point toward Lillard getting his way.

— Aaron Fentress | afentress@Oregonian.com | @AaronJFentress (Twitter), @AaronJFentress (Instagram), @AaronFentress (Facebook). Subscribe to Oregonian/OregonLive newsletters and podcasts