Trail Blazers star Damian Lillard will qualify for a Designated Veteran Player contract extension if he makes an all-NBA team at the end of this season. If he signs the extension this summer, however, he will only be able to extend his contract for four seasons, whereas if he waits until 2020 to sign the deal he can extend for five seasons. Check out a more detailed explanation here.

That final season would be worth over $50 million so it’s somewhat surprising to see Brian Windhorst report that Lillard is considering signing the extension this summer instead of after next season.

Why would Lillard sign the extension in 2019 instead of 2020?

Obviously, if Lillard does sign the extension this summer he can immediately lock in over $180 million in guaranteed salary. While losing the final year would be significant, the protection against injury concerns or other uncertainty may be appealing — especially after watching his close friend, Jusuf Nurkic, literally break his leg in half last week.

From a long-term perspective, if Lillard demands a player option on the back end of a four-year extension in 2019, he will become eligible to sign his last pre-38 years old contract in July, 2022 instead of July, 2023.

This is one reason Damian Lillard might sign an extension in 2019 instead of 2020. Takes one year off back-end of current contract, but allows him to sign his last pre-38 contract a year earlier.

Here's a possible contract timeline for Dame: pic.twitter.com/7xgveNm0tF

— Eric Griffith (@EricG_NBA) March 30, 2019

Moving up the timeline of a final contract that will be negotiated on the “wrong” side of 30 may offer protections against age-related decline in abilities or injuries and could actually maximize Lillard’s career earnings.

Would the Blazers offer Lillard a maximum

From the Blazers’ perspective, inking Lillard to a supermax contract does not come without risk, as Zach Lowe outlines here. Committing nearly $200 dollars to an athletic point guard as he enters his mid-30s can backfire. Other teams around the NBA have already shown buyer’s remorse with star players and massive contracts:

Man, those supermax deals are huge. We're going to be seeing a lot more Blake Griffin/Jimmy Butler style trades as teams weigh consequences of paying second-tier superstars that much. https://t.co/AaRjlMCEkG

— Eric Griffith (@EricG_NBA) July 27, 2018

With that said, the Blazers have little choice. Even if Lillard is unlikely to ascend to true-MVP level status, he is a bona fide top-10 player and shares a deep connection with the community and his teammates. If he wants to sign the extension this summer general manager Neil Olshey will not hesitate to give it to him.

Somewhat perversely, a deal in 2019 also gives the Blazers an out a year earlier if Lillard does suffer a catastrophic injury or significantly deteriorate as he exits his prime.

Does signing an extension now affect the Blazers’ cap situation?

Regardless of whether Lillard signs his extension this summer or next summer, the contract will begin in 2021. The 2021-22 salary cap will be used to calculate the year one salary of the contract, no matter what. In the unlikely event that Lillard does not sign an extension before his current contract expires he will still carry a significant cap hold. The Blazers gain no cap flexibility by waiting to sign the extension.

In short, Lillard signing the contract this summer has no impact on the Blazers’ long-term cap situation until the extension expires in 2024 or later. Unless the team has doubts about their superstar (that seems …unlikely) they should have no reservations about inking Lillard’s next deal ASAP.