As has been true since he was drafted in 2012, Damian Lillard remains the focal point of the Portland Trail Blazers franchise as they enter the summer ahead. Following a season of career-high statistical production, Lillard is looking forward to contending for an NBA Title, or at least making a run into the playoffs. The Blazers have not been able to help him towards either of those goals over the past two years, leading to increasing tension surrounding his tenure.
The Blazers have several decisions to make as the offseason commences, but the greatest of them is clear. Do they continue to build around their soon-to-be 33-year-old superstar, spending future assets and youth to pry open a window through which he can advance? Or do they pull down the curtain on the Lillard Era, emphasizing young talent and building up assets to make their next run at relevance?
We’re exploring that question in-depth in a two-part series. Yesterday we ran through some of the arguments for keeping Lillard. Today we’re going to take the opposite tack, looking at the reasons Portland and their superstar might need to part ways.
Here’s why trading Dame makes sense.
Stuck in Neutral
When the Blazers reached the 2019 Western Conference Finals, it looked like the promise of the Lillard Era was finally coming to fruition. A team featuring CJ McCollum, Moe Harkless, Al-Farouq Aminu, Rodney Hood, and (for 72 games) Jusuf Nurkic netted 53 regular season wins, defeating the Oklahoma City Thunder and Denver Nuggets to reach the third round of the NBA playoffs. They were swept by the Golden State Warriors, but the leap forward—made more impressive by Nurkic’s postseason absence due to injury—made the future look bright.
Four years on, only Nurkic remains from that list of Lillard’s teammates. In the interim, the Blazers have also tried Trevor Ariza, Carmelo Anthony, Hassan Whiteside, Gary Trent Jr., Norman Powell, Robert Covington, Derrick Jones Jr., Josh Hart, Larry Nance Jr., Justise Winslow, and Jerami Grant alongside Lillard. The summed result has been two first-round exits (3 wins in 11 total postseason games) and a pair of seasons missing the playoffs entirely.
If they were climbing the road to a championship, the Blazers are now stuck in neutral with the emergency brake off, rolling backwards.
Examining the lottery years... Lillard missed all but 29 games of the 2021-22 season. That helps explain their descent. But the team’s record when he left for abdominal surgery was just 11-18. He played 58 games in 2022-23, posting career-high numbers. Their fate was already sealed when he pulled the plug on the season for a second year in a row. They didn’t do poorly because he left; he left because they were doing poorly.
The Blazers absolutely, positively do better with Lillard on the court than they do without him. Both on/off numbers and win-loss totals show it. But nowadays the Blazers aren’t excelling—often aren’t doing well at all—even when Lillard plays.
Between 2015-2020, the biggest question in Portland’s book was how to build a contender around Dame. Now a second has crept in: Is it even possible?
If there is a correct mix for a Lillard championship in Portland, it may require drastic improvement...the kind that’s probably out of reach. Three years ago, the Blazers were hoping that Nance, Jr. would provide the final puzzle piece to push them over the top. This year’s trade rumors started with Joel Embiid before drifting through Jaylen Brown, Jimmy Butler, and Pascal Siakam. Those aren’t side helpers for Lillard. That’s a whole new team.
If the Blazers are carrying that kind of need into the offseason, they also have to face the reality that those players are almost impossible to get outside of fantasy fan trades. Opportunities are rare, costs exorbitantly high.
If the Blazers cannot obtain that level of co-star for Dame, they may have to admit that no lesser substitute will do. Overpaying for a player that won’t provide momentum on the mountaintop isn’t an option. That leaves Portland a choice between drifting further down the hillside with their superstar cranking a wheel no longer connected to the drive shaft, or simply trading Dame for a new vehicle and a chance to start over at the bottom.
Most of the cries to trade Lillard have nothing to do with his fitness. They’re an admission that the Blazers won’t be able to achieve their goals as currently constructed, making a rebuild inevitable.
If Portland can pull off a miracle trade, calls to move Dame will cease almost immediately. If the front office can’t make that happen, Blazers Nation may have to face the possibility that the “start over” skeptics have a point...if nothing else because Lillard himself will be running the same mental math in his head.
Age Gap
Perfect foresight would have called for more radical moves two to three years ago, when the Blazers were making the incremental changes mentioned above. That didn’t happen. Instead Portland stuck with their core as incumbent players and new additions became increasingly expensive. When they finally decided to change course, rising cost combined with decreasing wins forced Portland to deal from a place of weakness rather than strength in the trade market. They had to divest themselves of old obligations before taking on new.
In practice, that meant trading away McCollum for Josh Hart and a draft pick, then trading away Hart for young players and a pick. Ditto for Powell and Covington. When the dust settled, the roster sported a Grand-Canyon-sized age gap between Lillard and nearly everyone else who had come on board. The only significant players close to Lillard’s 32 years of age on the current roster are Grant and Nurkic, both 28. Other than that, Portland has become the 26-and-under club, with seven rotation players under 23.
That situation may be remedied by summer trades. Whether it should be is an open question. If the Blazers have to rebuild anyway, young talent is exactly what they’ll need going forward. If the Blazers were certain Lillard would remain no matter what, they’d probably consider using the third pick in this year’s draft to add to that group. Both Scoot Henderson and Brandon Miller are reported to be franchise-changing players. But Lillard himself has identified the age gap and suggested that he doesn’t belong on a team that keeps getting younger.
This lends an “us or them” quality to the generation gap. Not everyone is convinced that investing in a guard who will be 33 years old when the season starts is the correct definition of “us”, no matter what the stats say. Few are convinced that Lillard can wait for success, either. If they can’t revolutionize the team and can’t wait for a rebuild with Lillard on board, moving Dame is the obvious alternative.
Father Time
Lillard’s increasing age is lending urgency to the discussion. He had the best season of his career in 2022-23 at age 32. That’s giving the “Dame Will Last Forever” crew plenty of ammunition for their argument. It’s worth noting that he did this after taking nearly a full year off from basketball. He won’t have that rest coming into next season. Even if he puts up another banner year, what about 34 or 35? At some point his skills are going to diminish.
That impacts the Blazers in two ways.
First, if they trade the farm to get help for him, that help has to step up, gel, and pay out very quickly. This isn’t a four-year experiment. Every new season will be greeted with held breath, wondering if Dame can produce just one more time.
Just as crucially, if Lillard’s production diminishes, so will his trade value. Making an All-NBA Team while scoring 32 points per game makes him a promising trade target right now. If that drops to even 25, let alone 20, much of that value goes out the window.
That point is underlined when you read Lillard’s salary sheet:
2023-24— $45.6 million
2024-25— $48.8 million
2025-26— $58.5 million (estimate)
2026-27— $63.2 million (estimate)
Because of that contract structure, any team outside of Los Angeles or New York looking to take on Lillard will not only ask what he’s doing now, but what he’s likely to do down the road, and at what cost.
When he’s averaging 30, you can forecast a blinding impact immediately and hope for continued high-ish production later. If Lillard’s scoring drops, the calculus changes. Trading partners know Lillard is not a great defender. They understand that when he loses a step, and the threat of driving, his free throws will disappear and his three-point shooting is likely to be impacted too, as defenders guard up on him.
If Lillard’s production falls by 5-7 points per game, teams will wonder what the next drop will look like and when it will come. Nobody in the universe is going to sign up to pay an 18 PPG scorer $60 million per season.
That leaves Portland holding a volatile stock. Advocates for trading Lillard worry that, if the Blazers do not make that move now, they may end up with an unmovable, extremely expensive contract sitting on their ledger like a cement carving of an albatross.
If a championship were guaranteed next year, the risk might be worth it. But the difference between getting a haul for Lillard and getting nothing is fairly stark. With tomorrow uncertain, acting today—selling while the market is still fairly high—becomes more attractive.
What Time Is It?
In my non-Blazer’s-Edge life, I do a fair amount of Biblical study and interpretation. I know, sue me. It’s a thing.
Greek, the language of the New Testament, likes to parse the same concept into different words, each with its own shade of meaning. For instance, Biblical Greek uses two words prominently—“Chronos” and “Kairos”—when talking about the idea of “time”.
Chronos is your garden-variety day/year designation. What time is it? 5:15 PM. That’s chronos.
Kairos shades more towards opportune time, or the “right time” to do something. It’s best described by imagining a nine-month pregnant person saying to her partner, “Dear, it’s TIME.” At this announcement, a scramble ensues. Appropriate and urgent things happen no matter what the clock says. Chronos doesn’t matter at the moment, because it’s time to do the thing and no other time will do as well. Welcome to the concept of kairos.
Those who want to keep Lillard on the Blazers tend to think in terms of chronos. He’s only 32 (and Chris Paul is still playing for a contender at 37). He put up big numbers last season. He has lots of years left on his contract. Note that these are all static statements about Lillard, his individual qualities at this point in time.
Proponents of a Lillard trade argue more in the kairos sense. We’ve had a lot of years to try this. He probably isn’t going to get any better, and may get worse. He can’t win a championship with Portland, but he may be able to somewhere else. The Blazers might not be able to get much in trade for him later—or may not be able to at all—but they can now. It’s time to consider a move.
Also in the “opportune time” argument: if Portland has to start a rebuild, it’s far more advantageous to begin with the third overall pick in 2023, a roster of young players, plus a return for trading Lillard than it would be to cash out those things for another year or two with Dame, then have to start over later with the cupboard bare.
The “Trade Lillard” side is not disparaging Dame, his talents, or his contributions...at least most of them aren’t. That’s largely a fiction, brought about by people who don’t want to have the discussion in the first place. Instead of asking who Lillard is in isolation, trade advocates are also asking what time it is, arguing that should factor into the decision via the team’s timeline, a prospective rebuild, and the likelihood of winning a title in a short span of time if the Blazers don’t trade Dame.
It’s an uncomfortable conversation. Pondering mortality always is. But it’s a necessary one nonetheless, even when we’re talking about the era of the most beloved player in franchise history.
Pay to Delay?
Trade advocates are also asking what the Blazers would be buying with the extra time and money spent on extending Lillard’s tenure. More time with Lillard is guaranteed, but what else?
Over the last two years, time with Lillard has resulted in lottery trips...dissatisfying to all, including Dame. How do the Blazers get more victories, get back into the playoffs, reestablish themselves as a credible NBA team instead of floating along the river with the also-rans?
Arguments to keep Dame center around his irreplaceable internal qualities. But even Dame himself has said he’s not willing to ride out his career “being Dame” in Portland without considering victories and contention.
No amount of personal affinity will substitute for success. People point to Lillard’s character and genuineness, admirable traits that we’d all love to see in our sporting heroes. But there’s a certain amount of disingenuousness there from the fan perspective. We value those characteristics in this context because they are shown by people who play basketball at a world-class competitive level, bringing their teams victory. If we’re just talking really wonderful, giving, and solid human beings, we can comprise a team of Pacific Northwest citizens who would probably put any NBA team to shame. They’d be easy to root for as people. They’d also go 0-82 in an NBA season.
Without the skill, drive to win, and ability to compete, an NBA team will crumble from within while looking awful from outside. Personal characteristics augment, but cannot supplant, the central thing around which we gather, which is the sport. No player is bigger than that.
Again, the question at hand isn’t whether Lillard is talented or an amazing person. Everything we know says he’s both. It’s whether the Blazers will be investing huge swaths of their salary cap (and foregoing potential moves to improve over the long haul) just to miss success in the playoffs and frustrate everybody in the nicest, most charismatic way possible. If so, that’s not going to work for players, coaches, executives, fans, and probably not for Lillard himself.
The end of that road is the same as the “trade Dame” road: Lillard leaves, either via retirement or a later trade, and Portland has to start over. If the Blazers are going to reach that point anyway without earning a chance at a ring in the process, it’d be better to start the journey now than pay to put it off until it’s forced upon them.
Conclusion
There’s not a clear right or wrong answer to the question of whether to trade Damian Lillard. Ultimately, everything we’ve discussed on the pro and con side of the issue is going to factor in. It’s a matter of what each party values most.
Fans are divided in their responses. Their environment and requirements are quite different than those of the front office decision-makers and of Lillard himself. For those of us in the back seats of the bus, it’s easy to consult GPS algorithms and make pronouncements about the best way forward. The drivers at the wheel don’t have that luxury. They have to contend with road and traffic conditions, changes in destination, human limitations, and more.
I don’t have a gut instinct on which way the decision will shake out. My wisdom goes as far as this. All of us eventually reach the demarcation line between what we’d like to do and what we have to do. No critical decision in child raising, marriage or divorce, business, or health care comes without those agonizing moments of debate and realization.
This is not a happy thing. In many ways, it’s the worst step in the process. Any road that goes onward, even if it’s painful, is at least progress of some sort. There’s a relief, having taken those steps. You’re able to process the stress and grief, then move past them.
Until you’re able to clearly identify what that “have to” is, and how much of the “want to” it’ll cost, angst and anticipatory grief shoot through the roof. That’s exactly where Portland fans are now. The best that can be hoped under such circumstances is to discern clearly, decide wisely, and walk together compassionately no matter which way the road goes.
Plenty of things could have turned us aside from this juncture. The Blazers might have made more productive moves, turning themselves into a Nuggets-like, or at least a Kings-like, playoffs team. Lillard might have stepped up to a microphone and said clearly, “I am staying in Portland for my entire career no matter how young the team gets or what the progress arc becomes.” The injury bug might have bitten less harshly. LaMarcus Aldridge might have not left for the San Antonio Spurs. The final ping pong ball in this year’s lottery drawing might have come up for Portland instead of those same Spurs.
None of that happened. The Blazers are where they are. There’s no hope of avoiding it, even less in trying to rationalize it away. The best that can be hoped for is further good outcomes in the future and everybody—including Lillard, the team, and the fans—treating each other well along the way, no matter what.