The Portland Trail Blazers got stomped by the Milwaukee Bucks by a score of 127-108 earlier this week. That's nothing new for a Portland team that has rarely sniffed true contention over the past decade. During the Damian Lillard era, the Blazers have finished above .500 against teams with a record of .500 or better only once, during the 2018-19 season, which also happens to be the last time this team won a playoff series.
It's a fitting statistic for a frustratingly mediocre era of Blazers history. Having Lillard has kept the Blazers afloat for years. He's helped them make the playoffs eight times. Once there, he's more than held up his end of the bargain with a number of stellar performances. But ultimately, when the Lillard-era Blazers run up against true championship-caliber competition, they lose.
Lillard has never shied away from the Sisyphean task the Blazers have laid before him. Every year at this point on the calendar there are teams trying to pry him away from the only NBA home he's ever known, and every year, he makes it clear that he's not interested in going anywhere. This happened again Thursday, when Bleacher Report's Chris Haynes reported the Blazers have told other teams that Lillard is not available at the 2023 NBA trade deadline.
For the time being, Lillard doesn't seem to mind pushing that boulder up the hill, and the Blazers have never been inclined to stop him. NBA teams rarely consider moving stars in their prime who want to stay put. It's easier to remodel everything around them and hope the latest cosmetic changes are enough to distract from the rotting foundation. Maybe a new coach will fix this? No? How about a redesigned, wing-heavy roster? Surely that'll get things back on track.
Thus far this season, it hasn't. Since starting 9-3, the Blazers have gone 18-25. They have the NBA's ninth-worst net rating since then and its fourth-worst defense for the season as a whole. Swapping out smaller guards like C.J. McCollum and Norman Powell for heartier wings like Grant and Josh Hart (who was traded to the Knicks on Wednesday) has done little to solve this team's underlying defensive flaws. There's not much evidence to suggest at this point that Chauncey Billups is a better coach than Terry Stotts, and lest you believe there is a blockbuster trade on the horizon that could fix this, remember that Portland owes a first-round pick to Chicago that has protections that last until 2028. Therefore, for the time being, The Blazers can't even trade a first-round pick without removing those protections. Doing so means handing the Bulls a possible lottery pick in June.
There will probably be more lateral changes in the coming months. Portland will likely replace Hart with their mid-level exception in July. Perhaps the Blazers will trade for a center more mobile than Jusuf Nurkic. It's hard to take the idea of such moves too seriously in the greater context of Lillard's career. He's played on almost every kind of team at this point. He was part of a traditional guard-big star tandem with LaMarcus Aldridge early on before transitioning into an offensive juggernaut with McCollum for the bulk of his prime. Now the Blazers have attempted to strike more of a balance between offense and defense, and it has thus far yielded uninspiring results. Lillard has now played for two coaches, two general managers and two owners. The results have never really changed. The only untouched variable in the equation is Lillard.
Lillard isn't at fault for what's gone wrong in Portland. He's one of the few things that have held the Blazers together despite years of poor management, and the stakes to keeping him for all of these years were relatively low. He's happy in Portland. Blazers fans are happy to have him in Portland. There's nothing necessarily wrong with winning 45 games every year when better options don't present themselves, but the longer they do it, the harder it's going to be to change course. Sooner or later, it would probably behoove the Blazers to actively choose a direction for their franchise.
Behind Door No. 1 we have the definition of insanity. The Blazers can keep trying to put a winner around Lillard. Maybe they strike gold on an under-the-radar transaction. Maybe they can pool their young players into an impact veteran. Maybe Lillard convinces a star to join him in Portland. It's not inconceivable. Kevin Durant has a well-known fondness for Lillard and asked for a trade eight months ago, after all. Sometimes all it takes is being at the right place at the right time. The Toronto Raptors weren't dissimilar to the Blazers a few years ago. Kawhi Leonard won them a championship.
But relying on such fortune as a small-market team with limited trade resources carries its own risks. Lillard is 32 and will likely begin to decline soon. He's under contract through 2027, and if that decline comes as scheduled, that deal could hamper the next half-decade of Portland roster-building. It's far likelier that the Blazers spend the remaining years of Lillard's prime as they've spent the bulk of it so far. A Grant here, a Hart there. Good players that don't make sense without another great one. Doing the same thing over and over again and expecting different results.
Behind Door No. 2, we have the unpopular unknown. Portland's second-best player is probably the 23-year-old Anfernee Simons. Shaedon Sharpe is still a teenager, and considering it took Simons four years just to reach a double-digit scoring average, he probably has some uncomfortable developmental years ahead of him. The flashes of upside are there, just as they have been for young forward Nassir Little. Move Lillard now and the Blazers could still get a haul for him to pair with those youngsters. A couple of years in the lottery wouldn't hurt either.
There's no certainty to that path. Maybe Simons and Sharpe, with better supporting infrastructure, can grow into a better version of the Lillard-McCollum backcourt that came up literally and figuratively short. Maybe giving away Lillard leads to a decade in the wilderness as the Dwight Howard trade did for the Orlando Magic. The only way to find out is to take the plunge.
Doing so would mean ignoring the very publicly expressed wishes of a franchise icon. No executive wants to be remembered as the man who traded the best player in franchise history. But NBA history favors teams that moves stars proactively. Oklahoma City and Utah are positioned quite well moving forward thanks to the star trades they've made in recent offseasons. The longer you wait, the less value you can extract. Lillard is still a star at 32. He may not be at 34.
And if he's around at 36? He's probably going to be taking up shots, minutes and dollars that would be better utilized maximizing Simons and Sharpe. Throwing away one era out of sentimentality is one thing. Letting it drip into the next is significantly more dangerous. The Lillard era started at an inherent disadvantage given the veteran-laden roster he initially joined. Once Aldridge and several other key Blazers left, Portland simply lacked the tools to rebuild adequately. Lillard was too good to tank, but without getting anything back for the departed veterans, the Blazers had no way of replacing what was lost. It's a cycle the Blazers should not be eager to repeat.
Yet it increasingly feels like their destiny the longer they pretend that there's a viable path to putting a championship team around Lillard. They've spent a decade trying and failing to do so. Lillard might want to spend another decade pushing that rock up that hill, but eventually, the Blazers need to acknowledge that the best interests of the franchise shouldn't be superseded by the wishes of a single player. The Lillard-centric version of the Blazers are never going to be able to compete with the Bucks of the world. Separating has always been Lillard's best path to doing so, but the longer this drags on, the more evident it becomes that it is Portland's as well.