All summer, it seemed inevitable. Star point guard Damian Lillard was decidedly unhappy with the Portland Trail Blazers, after a first-round ouster in the NBA playoffs and, eventually, the firing of Terry Stotts and hiring of Chauncey Billups. That hire brought back into light a sexual assault accusation made against Billups two decades earlier, and the way the organization—especially team president Neil Olshey—handled a so-called “investigation” into the matter made the Blazers look supremely inept.
Lillard, who had been so staunchly committed to winning in Portland during his 10-year career with the team, had an oddly uncertain summer. The Sixers took notice. In July, while Lillard was practicing with Team USA, he very cryptically said, “I haven’t made any firm decision on what my future will be.”
That has changed drastically. Even as Lillard has struggled this season, he has backtracked on his uncertainty. Less than three weeks ago, Lillard said in an interview with The Athletic, “Everybody is saying what they think I’m thinking, and what they think I’m going to do, but like, I’m not leaving Portland, you know?”
But league insider Kevin O’Connor of the Ringer says Dame’s sudden 180-degree turn on a Portland exit is suspicious in the eyes of many NBA executives, and could be just the first phase in a Lillard blockbuster.
“He goes from making these vague comments about, ‘Yeah, I don’t know how long I’ll be here,’ like weeks before the season to suddenly, ‘I’m all in,’” O’Connor said on the Mismatch podcast. “There are front office executives around the league who think this is a strategic choice by the Blazers, Dame’s group and all that in order to create leverage for the organization because right now around the league teams just want Dame. They don’t they don’t want C.J. McCollum, they don’t want Jusuf Nurkic. They’re like, ‘We’re gonna wait for Dame to demand a trade.’”
Lillard Raising Trade Value With Portland Allegiance
In other words, if Lillard is serious about wanting to be traded, he is doing exactly what he should be doing, sort of the opposite of what Ben Simmons is doing in Philadelphia—Lillard is putting on a happy face and announcing his happiness in Portland.
That way, when the Blazers field calls from teams seeking a Lillard deal, the team won’t be dealing from a position of weakness, as the Sixers are. If O’Connor is right, that could be good news for the Sixers. Lillard remains atop the team’s wishlist.
Back when Lillard first let his uncertainty be known, he set off a wild string of rumors that had Lillard landing in all sorts of new locales: with the Knicks; with the Sixers, where he could be swapped out for Ben Simmons; with the Lakers, who, Lillard admitted this past week, recruited him in the offseason. Miami was a potential suitor, too, before the Heat acquired Kyle Lowry.
Throughout the the Simmons saga, the Sixers have held out hope that the Blazers, who have been naturally reluctant to put Lillard on the market, will relent and discuss a Lillard-for-Simmons swap. GM Daryl Morey has been eager to hang onto Simmons until he can get a star in return, but no such offers have been forthcoming. Still, any attempt Philadelphia makes to bring in a star will be built around Simmons.
Lillard is not cheap. He is in the first year of a supermax extension he signed in 2019, which is slated to pay him $195 million, including $43 million this year. Simmons is in the second year of a five-year, $170 million contract extension and will make (minus fines, at least) $31.6 million this year.
Philly would undoubtedly have to give up more than Simmons to get Lillard back, and they’re one of the few contenders in position to offer picks and young players. While Tyrese Maxey is likely off the table, the Sixers could consider some combination of young guys like Matisse Thybulle, Furkan Korkmaz and Shake Milton to sweeten the pot. The Sixers owe a 2025 first-round pick to Oklahoma City, and, thus, can’t trade their 2024 or 2026 picks, by NBA rule, but could offer a 2022 or 2023 first-rounder to Portland.
Olshey Investigation Could Speed Lillard’s Departure
The makings of a deal have always been there for Portland and Philadelphia. The problem has been the Blazers’ unwillingness to part with Lillard or, more specifically, Olshey’s unwillingness. That could be coming, or he could already have a wink-and-nod agreement with the team ahead of an impending trade, as O’Connor suggests.
Complicating matters—or, perhaps, making the road to a trade easier in the end—is the fact that the Blazers are being investigated for a “toxic work environment” under Olshey, who has long held the “no way” position on even discussing Lillard deals. He has a lot invested in making Lillard successful, and has not considered putting Portland through a rebuilding phase.
But it now appears inevitable that Olshey will lose his job, either by resigning or being fired. A new head honcho in the Portland front office, many around the league say, would be the key to Lillard getting traded.
Lillard has been saying he is committed to Portland. But that might, in the end, be setting up his departure—and the Sixers will be at the front of the line when it happens.