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What a Supermax Extension Would Mean for Damian Lillard and the Blazers

On Tuesday, reports surfaced that Portland is trying to sign its star player to a pricey extension. While that deal seems like a no-brainer on the surface, it would leave the Blazers with a lot more questions than answers.

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With playoff elimination comes the harsh reality of the NBA offseason—namely, the team-building talk that excites fans of the league but probably has general managers pulling their hair out. The Blazers are extremely familiar with this cycle. They have been routinely questioned for keeping their backcourt together and challenged over roster decisions they’ve made after disappointing seasons. And even though the team made the Western Conference finals this season—vastly outperforming preseason expectations following a first-round loss in last year’s playoffs—after getting tidily swept by the Warriors, those questions are popping up again. But at least one of them seems like it may already have an answer.

On Tuesday, Yahoo’s Chris Haynes reported that Portland and Damian Lillard—he of the series-clinching, game-winning buzzer-beater over Paul George in Round 1—are working toward a supermax deal, which Lillard is eligible for this summer because of his forthcoming All-NBA standing. If the team and city and player hadn’t been weaved together in such a tight fashion already, that shot sealed it: If the Blazers can help it, Lillard will not play for another franchise for the rest of his career.

The 28-year-old was one of the best players in the league this season and is fully deserving of both the accolades and the cash coming his way. That’s impossible to argue with. But take a closer look at the yearly breakdown of said supermax extension, and your eyes begin to widen. According to ESPN’s Bobby Marks, the new deal would kick in by 2021, giving Lillard $42.6 million in 2021-22, $46 million in 2022-23, $49.4 million in 2023-24, and $52.8 million in 2024-25; by that point, Lillard will be 34 years old.

To be clear: Given that Portland hasn’t historically been a top free-agent destination, plus the fact that Lillard has repeatedly voiced his desire to stay and play for the Blazers, the front office should not (and probably will not) think twice about giving him that deal. But the details of the reported deal still present a few questions: How will Lillard perform in his mid-30s, the age range where players have historically tailed off? How will Portland build a contender around that deal? These realities were exactly what the Sixers were trying to avoid when they went all in this past season; the cost-controlled contract of Ben Simmons gave them a window to try and win before money handcuffs them.

The supermax conversation is a fraught one, not just for Portland, but for the other teams around the league who have faced it, and those who will down the road. Designed as a way to keep stars with the teams that drafted them, it has instead forced players who want to leave to ask out before the extension negotiations even happen (like Paul George), forced teams to preemptively trade players who were likely to leave (DeMarcus Cousins), seen teams trade players after they signed the deal (Blake Griffin), or hampered teams to the point that building around said player becomes like solving a Rubik’s cube with a blindfold on. Take the Wizards. They gave John Wall a supermax extension in 2017, and then he injured his Achilles in February and may not play next season (or be fully himself on the court ever again)—all as his supermax is set to kick in this fall, which will have him making over $47 million by 2022. It’s a precarious situation, both for the team that’s saddled with such a contract, and for the player who has to somehow play up to the unrealistic expectations of such a gaudy deal. But the Blazers don’t seem to have much of a choice.

There are a couple of unknown factors as to the effect Lillard’s extension would have on the Blazers over the next few seasons, namely that we’re not sure what the cap will look like two, three, or five years from now. A cap rise over the span of Lillard’s would-be contract is likely, but will it be incremental, or a high jump like it was in the summer of 2016? That will determine what percentage of the Blazers’ cap the supermax would take up, and subsequently how much of a roadblock it would become in team building. Another factor is the sale of the team, which is reportedly likely to happen sometime in the next few years, since owner Paul Allen died in 2018. The Lillard extension may be part of the package the forthcoming ownership will have to deal with. Then again, locking down Lillard could also be a way to show stability and lure in another high-level player to the team.

Regardless, the onus will fall on the front office and general manager Neil Olshey to figure out how to shape the surrounding roster—most importantly, how to add a reliable wing or stretch big (sorry, Meyers Leonard). Portland has little organic room for improvement next season, outside of hitting on a lucky draft pick (Anfernee Simons’s skill level is still TBD), a certain free agent falling in love with the Portland coffee scene, or a drastic move like trading a core player. Then comes the question of whether Zach Collins or C.J. McCollum is an attractive enough option to put in a deal to get a better piece.

No matter how you slice it, though, the question of Portland’s backcourt is what we always seem to return to, if only because McCollum is the most valuable non-Lillard piece the Blazers have. While they’re a dynamite duo in their own right, for as long as Lillard and McCollum remain in their prime, Klay Thompson and Steph Curry will likely be in theirs too. And even if the Lillard-McCollum twosome can come close to matching the Warriors’ backcourt on a good day, Portland needs—and really, for years has needed—something else to push it over the top. In an ideal world, that would come as an addition to Lillard and McCollum, but with money constraints on the horizon, the Blazers may not be able to afford running it back.