The Damian Lillard saga: How things are shaping up and what factors are in play

With the final days of September leading toward training camp across the NBA, the Portland Trail Blazers have increased conversations with rival front offices this week in an effort to conceive the greatest possible return for seven-time All-Star Damian Lillard, league sources told Yahoo Sports.

Since the initial July talks stemming from Lillard’s trade request did not result in a deal to his preferred destination of Miami or another potential landing spot such as Brooklyn, the beginning of training camp — and media day Oct. 2 — has loomed as the unofficial deadline for Portland to part with Lillard and start a new Blazers era in earnest. That's even more so than the ongoing dynamic in Philadelphia, where James Harden still hopes to be moved to the LA Clippers, sources said.

The Blazers have young lottery picks in Scoot Henderson and Shaedon Sharpe, plus 24-year-old scorer Anfernee Simons. Bringing back Lillard, 33, with four years and more than $200 million remaining on his contract — especially after such a public spectacle — works in complete contrast to Portland turning the page to a next chapter in which the main characters are already in place. Philadelphia staffers, meanwhile, can still talk themselves into the idea of Harden reporting to camp, playing for a title hopeful and, therefore, playing his way into the trade value the Sixers require to relinquish the All-Star. How realistic is that? Well, Harden has already claimed that he’ll never be part of an organization that Philadelphia president Daryl Morey is a part of.

There are more fireworks coming with the Sixers, whether at their Camden, New Jersey, practice facility or when the team briefly relocates to Colorado Springs, Colorado, for training camp. Portland’s situation is quickly progressing toward a cleaner resolution, as increased chatter surrounding potential trade partners outside of Lillard’s preferred Heat has reverberated around the league. Just how quickly the Blazers manage to bring negotiations across the finish line will depend on how general manager Joe Cronin and his front office wrangle the various multiteam frameworks Portland has explored in recent days, according to league personnel familiar with the matter.

At this juncture, Toronto and Chicago have been the two possible destinations for Lillard discussed most by league figures. While a collection of NBA personnel expect Portland to engage Miami before finalizing something with another suitor, the Heat have not factored primarily in the Blazers’ recent dialogue surrounding Lillard, league sources said. Additionally, the Phoenix Suns and Utah Jazz have materialized as peripheral teams that could factor into larger deals that help facilitate Lillard’s departure from the Blazers.

Assembling such a blockbuster requires the summation of many parts. One piece of the developing Lillard negotiations that seems clear: Portland has strongly considered acquiring Phoenix Suns center Deandre Ayton as part of a multiteam deal for Lillard, league sources confirmed to Yahoo Sports. Arizona Sports and PHNX previously reported the Suns’ potential involvement.

The Blazers have registered interest in Ayton in the past, sources said. This current idea appears focused on sending Portland center Jusuf Nurkic back to Phoenix, therefore supplying the Suns with a suitable defensive anchor for new head coach Frank Vogel and a pick-and-roll partner for Phoenix’s array of perimeter playmakers who is not expecting the volume of touches Ayton is believed to desire on offense.

This is a tricky dynamic for the Suns to balance, being that Phoenix maintained that Ayton was not available for trade this summer, sources said, as Vogel publicly supported the former No. 1 overall pick as having “All-Star-level” talent during his introductory press availability. If a trade for Nurkic never comes to fruition, the Suns need Ayton in their hopes for a title behind Kevin Durant, Devin Booker and Bradley Beal. What they do not need is a potentially aggrieved big man who thinks the Suns were actively trying to move him for Nurkic. Yet there's an argument to be made that splitting Ayton’s contract on Phoenix’s books into two valuable rotation pieces would provide Vogel with significant depth and boost those championship aspirations.

Nurkic’s average annual salary of $17.5 million is roughly half of Ayton’s $33.2 million paycheck, so there’s additional accounting that would need to take place to satisfy this part of the Lillard puzzle. Adding perhaps the $18 million salary of Raptors forward OG Anunoby would help match the money in the event that Masai Ujiri’s front office finally moves on from one of its prized core pieces, having flirted with several trade scenarios before the February deadline and throughout this offseason. All that flirting with little outcome — aside from adding back Jakob Poeltl — has left plenty of NBA figures skeptical that Toronto will actually pull the trigger.

Moving Anunoby and other compensation for Lillard, though, is a much different prospect than moving him for picks from a team such as Memphis or New York. But what goes back to the Blazers? And if you’re Portland, could the chance of moving Anunoby rekindle conversations with suitors such as the Knicks and add to the greatest possible return Cronin’s staff seeks? Otherwise, maybe Anunoby simply sticks around in Portland.

There are plenty of avenues to evaluate, which makes the Raptors one of, if not the most viable threats to land Lillard outside of the Heat — similar to the Cavaliers’ surprise acquisition of Donovan Mitchell last September. Don’t count on Scottie Barnes, however, being the blue-chip centerpiece of Portland’s return. Toronto has made clear to all inquiring parties that Barnes stands as the Raptors’ franchise focal point, sources said. Any deal with Toronto could include recent first-round selection Gradey Dick, sources said, just like then-rookie wing Ochai Agbaji and then-rookie center Walker Kessler both functioning as additional draft compensation in Utah’s returns for Mitchell and Rudy Gobert, respectively, last offseason. In any deal with Miami, league personnel expect Portland to ask for the Heat’s recent first-round pick, Jaime Jaquez Jr., as well.

It seems unlikely that All-Star forward Pascal Siakam would fit into a package for Portland. Siakam is entering the final year of a lucrative contract and hasn't yet completed the pricey extension he’s eligible to sign. Paying Siakam would be a curious commitment from the Blazers after they awarded Jerami Grant a five-year, $160 million deal in July, when Portland was not considered interested in backing Siakam’s next contract. And would the rebuilding Blazers really make long-term sense for an in-his-prime All-NBA talent?

Anunoby brings his own share of financial considerations. The 26-year-old swingman has a player option for the 2024-25 season, took meetings with several agencies before leaving Klutch Sports for CAA and informed various representatives, sources said, that he is looking for greater ball-handling opportunities that can result in a commensurate salary increase. Maybe there’s more chance of that in Portland, where Barnes’ development won’t stand in the way of Anunoby’s. It’s difficult to imagine Phoenix fitting Anunoby’s next deal into its exorbitant payroll — as part of the three-team concept described above — but if there’s any ownership group currently willing to splurge to that degree, it’s this Suns leadership.

For whatever level of activity Chicago has here, the Bulls don’t bill as strong of a partner as Toronto for what the Blazers are attempting to achieve. Chicago has explored trade scenarios for Zach LaVine throughout this offseason, league sources told Yahoo Sports, yet Portland does not appear keen on acquiring the All-Star guard. The Blazers have a score-first uber-athlete in Simons, who has not reached the level of LaVine’s production but is also four years younger and commands nearly half the salary. Perhaps Chicago can reroute LaVine to another destination and use that package to engage Portland, as mentioned on PHLY. There just doesn’t seem to be a robust market for LaVine’s services, with his salary and injury history. His availability has been known around the league since July, yet he remains in Chicago.

Keep an eye on Utah playing a potential role in a three- or four-team outcome of these Lillard conversations. If Portland ultimately does business with Miami, the Jazz — as well as the Bulls, Hornets and Nets — are considered a team interested in landing Tyler Herro from the Heat, sources said. And there are plenty of executives who’d rather take Miami’s best package, if the Heat are so willing, that could include Herro and Nikola Jovic to go with Jaquez, Caleb Martin and more.

Many of these dots will connect and direct Lillard from the Blazers to another franchise some day soon. How many actually come together and how many other teams and players get shuffled in the process will depend on what Portland’s front office thinks is the best package it can garner — whether rival personnel and fans agree or not.