So Damian Lillard’s time with the Portland Trail Blazers might actually be ending soon. A report from Yahoo Sports suggests there’s some level of dissatisfaction with the coaching search and the continued struggles to put a winner around him, which might mean Lillard might want out.
When a disgruntled superstar starts looking for a new home, the fans of most other teams start firing up the trade machine. Boston Celtics fans, in particular, may be clamoring for one of the most clutch players in NBA history to join a team that seemed to be lacking that level of desire this season.
Unfortunately, this one doesn’t look very likely. As amazing as Lillard has been, as fun as it would be to watch him every night, there are a lot of reasons why this would be the wrong move.
LILLARD’S AGE
Lillard turns 31 in a couple of weeks. That’s not horrible, but it’s tough for Boston in a couple of ways.
First, he’s a smaller guard in his 30’s, and smaller guards in their 30’s historically age quickly. Lillard has been pretty durable, but things can change in a hurry for guys like Lillard. He may be the exception to the rule, but it’s still a concern.
Second, he doesn’t fit the timeline. Jayson Tatum is 23 years old, and there’s a team being built around him and 24-year-old Jaylen Brown. If significant assets are going to be moved, the Celtics had better be sure they become championship contenders when a deal is done because Lillard, healthy or not, doesn’t have a lot of time left at this level of stardom.
LILLARD’S COST
This is the real issue. Lillard will make $39.3 million next season, $42.5 million the season after that, $45.6 million the following season, and then he has a player option for $48.8 million for the season in which he turns 34.
Carrying the first section into this one, owing a small guard about $94 million at age 33 and 34 is risky no matter what. This is why it’s especially important to feel sure that acquiring him would vault Boston into the top tier of contenders. If we assume he has a couple of top-tier, mostly healthy seasons left, then the window for the Celtics is small.
And it’s not really clear how the Celtics can come out of a Lillard trade as contenders because part of the cost would be Jaylen Brown.
Lillard is better than Jaylen Brown right now, but (a) just how much better is he and (b) how long will it take for that to no longer be true? At some point, Lillard’s eventual dropoff and Brown’s continued improvement will cause those lines to intersect.
There’s no real way to make this deal work without Brown. The Celtics can’t really put together a feasible trade package with their other contracts, and they can’t make up for that with a stack of draft picks. Brown would be the prize for Portland, allowing them a fairly quick pivot around an established but young NBA star.
A Brown-centric package makes the timeline even smaller for Boston, but it also puts them in a precarious position because the final year of Lillard’s contract would be the fourth year of Tatum’s extension, meaning he’ll be opting out and becoming a free agent.
Tatum is the priority in Boston, followed closely by Brown. If Brad Stevens were to get rid of Brown and go all in on a plan centered around Tatum and Lillard, he’d better be sure the supporting cast is good enough to get past the East’s best.
It’s one thing to bet on a Tatum/Brown/(insert third star’s name here) trio and rely on a thin bench of veteran and mid-level guys. If that third star doesn’t work for some reason, at least the Celtics would have Tatum and Brown and they could pivot to something else.
If they bet on Tatum and Lillard and it goes south, Tatum will look around him as he enters his prime and wonder if there’s any salvaging that can be done. That summer of ‘25 is the year a new TV deal will kick in, and it’s possible most of the league will have significant cap space.
So which position would you rather be in? Having Tatum, Brown, and cap space in case the third star plan doesn’t work, or having Tatum, Lillard, and a league flush with cash?
Getting Lillard would be amazing in the short term. Even if it cost Brown, the Tatum/Lillard combination could be tantalizing. But the risk is too big. The Celtics stand a strong chance of not only coming out of all this with nothing, but with the Blazers holding the draft picks Boston would need to start rebuilding.