How Damian Lillard and the Trail Blazers are Moving On From Each Other
As Lillard prepares to return to Portland for the first time since being traded, both the franchise and its all-time leading scorer are in an uncertain place.
The most surprising thing about covering this Trail Blazers season is how little I’ve thought about the absence of Damian Lillard.
Maybe it’s just because the trade happened so soon before training camp and then there was a whole new roster to figure out and get to know, but his name really hasn’t come up much. I’ve followed his season in Milwaukee closely, as I’m sure most of you have, but covering a team daily can mean a lot of tunnel vision about what’s in front of you.
I spent yesterday evening watching two people I know very well, Blazers team photographer Bruce Ely and TrailBlazers.com beat writer Casey Holdahl, put on a photo gallery of their work documenting the first 11 years of Lillard’s career, which included shots of both his most iconic on-court moments and scenes with his kids. They took questions about what it was like to be there every step of the way as he became, well, the guy worthy of all the fanfare that’s going to come tonight. And then you remember: this game is going to be a pretty big deal.
People have asked me lately if I’m looking forward to Wednesday. My default answer has been, “I’m looking forward to Thursday.”
When the NBA released its 2023-24 regular-season schedule in August, the Blazers’ only nationally televised game was one in late February against another Eastern Conference team that has since been dropped (you do the math as to why). After Lillard was traded to the Bucks in September, ESPN picked this game up. It’s the most attention the Blazers will have on them nationally all year, and for good reason. Rebuilds are long and often unglamorous.
For the 11 years Lillard was here, Portland was usually in the national consciousness, either as a playoff contender or the subject of Lillard trade speculation and intrigue. Now that they’re on the other end, they’ve been largely off the radar. And Lillard has been in the spotlight in a way he never was in Portland, as a newcomer to a Bucks team that’s expected to be in the Eastern Conference Finals at the very least. It’s been an adjustment all around.
Once a summer of interminable rumors and leaks finally culminated in a deal getting done less than a week before the start of training camp, a general consensus emerged: Things worked out better for everybody in the end. Blazers general manager Joe Cronin did better in the deal he made with the Bucks than he would have done if he’d had to trade Lillard to the team most people thought he’d end up on, and Lillard landed in the best situation possible to compete for the championship he was never able to here.
In their first year apart, both sides are seeing what life looks like on the other side—for good and for bad.
As soon as the Blazers traded away their all-time leading scorer, everyone knew what the reality of the next few seasons was going to be, at least from the standpoint of competing for the playoffs. But even the most clear-eyed realists may have underestimated how much just having a stabilizing presence like Lillard who also happened to be their best player covered up.
In talking about what he was expecting from Lillard’s return, Chauncey Billups admitted that having him around for his first two seasons as a head coach made his life easier, for reasons that had nothing to do with what he did on the court.
“A guy like him just cleans up everything that the coach doesn’t have to worry about,” Billups said. “In the locker room, on the floor, he made it very easy for me.”
You take away that constant from the organization, and you’re left with a team finding its voice.
Billups’ controversial comment from December about the Blazers’ lack of an “alpha” was actually about the team’s pattern of getting off to slow starts, but it got at the reality of the hole Lillard’s departure has left in the locker room.
It’s a good group, but who’s the leader?
Anfernee Simons, who has by far played with Lillard the longest of anybody still here, has become much more vocal since he came into the NBA as a teenager who barely said a word, but he doesn’t come with the cache of being an All-Star while being that voice.
Jerami Grant? Universally liked, but quiet and unassuming.
Deandre Ayton? Also well-liked, but goofy and too easy of a target.
Scoot Henderson? Has the natural charisma and magnetism, but also 19 years old. Maybe in time he’ll become that guy, but he isn’t yet.
Malcolm Brogdon? The most tenured and respected veteran, who has thus far embraced a mentorship role, but everyone knows he isn’t going to be here for the long haul. If he isn’t traded at the deadline, he almost certainly will be in the summer.
There’s no one that checks all the boxes Lillard did. Not that there are many in the league who do. But when a franchise had one of those guys for a decade, the absence becomes glaring.
And just as the Blazers organization is getting used to not being built around one personality, Lillard is getting used to not having everything built around him. In Portland, the conversation for years was centered around whether they’d be able to get him a second star. He came to Milwaukee as someone else’s second star, and he’s had to adjust to it.
He’s never played with someone as good as Giannis Antetokounmpo, or entered a season on a team with legitimate championship aspirations. Neil Olshey made a media-day tradition out of calling rosters with minor tweaks and no true second star the “strongest” or “deepest” they’d ever had, but everyone knew deep down that they weren’t on the level of Golden State or the other Western Conference contenders. Now that the expectations are different, the flaws and shortcomings become much more scrutinized.
Lillard has also never been a part of a team that fired its coach midseason, as the Bucks did earlier in the month with Adrian Griffin to bring in Doc Rivers. When there was chaos in Portland, it was always in the offseason—LaMarcus Aldridge leaving in free agency in 2015 or the way the coaching search was handled in the summer of 2021. The most disruptive thing that happened in-season during his time in Portland was Olshey’s investigation and firing in December of 2021; by that time, their season had already gone off the rails and Lillard was trending towards season-ending core surgery. What’s happened recently in Milwaukee—a 32-15 record masking an underperforming defense and locker-room issues that have been well-documented in the days since Griffin’s firing—is new to him, and in his new home, he can only do so much to fix it.
Everyone has their theories about how Wednesday night will go. This might look silly in about 12 hours, but I think Lillard is going to have a bad game. I’ve seen this happen too many times, and covered it firsthand in my former life on the Bulls beat when Dwyane Wade played in Miami for the first time as a visiting player. The homecoming game for an all-time franchise icon messes you up. You walk into the building and forget you’re supposed to go to the visitor’s locker room. You have a limited amount of time at home to sleep in your own bed and you have people fighting for your attention constantly. There are extra media obligations. It’s just a lot to deal with, and I think Lillard will be happy when it’s over with.
The Blazers will also be happy to have this game behind them. I don’t know whether Lillard and Cronin will talk on Wednesday night. In the immediate aftermath of the trade, there were very public hard feelings between them over the way the summer played out. I wrote at the time that I thought they’d eventually get past it, and I still think that. Even in his goodbye letter following the trade, Lillard soft-launched the idea of ending his career in Portland.
There will be a tribute video, a lot of reunions and a lot of cheers. And then both Lillard and the Blazers will get back to basketball.