Damian Lillard is on his way back to Portland.

The Trail Blazers legend agreed to return to Portland on a three-year, $42 million deal following a contract buyout with the Milwaukee Bucks earlier this offseason. The signing obviously won’t make the Blazers contenders right away, especially with Lillard expected to miss most, if not all, of the 2025–26 season as he recovers from an achilles tear suffered in the first round of the 2025 NBA Playoffs. However, it does include a secret impact that will benefit the future of the Chicago Bulls in the very near future.

Late in the 2021 offseason, the Chicago Bulls were involved in a three-team trade that sent Lauri Markkanen to the Cavaliers, Larry Nance Jr. to the Trail Blazers, and Derrick Jones Jr., along with a lottery-protected first-round pick to the Bulls. Since that deal, the Blazers have remained near the bottom of the league in standings, allowing them to keep their draft pick each year.

While Lillard’s return to the place he called home for 11 years doesn’t guarantee anything, it does give the Bulls their best shot at turning this pick into a real asset before it eventually converts into two second-rounders if the Blazers fail to make the playoffs over the next three seasons.

Why Lillard’s return changes everything

As mentioned earlier, Lillard is expected to miss the entire 2025–26 NBA season after tearing his achilles nearly three months ago. If this signing holds any relevance for the upcoming season, specifically, it’s that the Trail Blazers appear to be shifting towards a win-now approach.

Portland has done a great job drafting in recent years, building a young core that includes Shaedon Sharpe, Deni Avdija, Donovan Clingan, Scoot Henderson, and Yang Hansen. Additionally, they’ve also been able to add veterans in Jrue Holiday and Jerami Grant via trade. This group could be capable of making a playoff push, but may still fall short, given the expected depth of the Western Conference.

It’s the two seasons following Lillard’s rehab year that should intrigue Bulls fans the most. Lillard will be under contract through the 2027–28 season (including a player option in the final year), the same year the pick protection expires. If the Blazers make the playoffs in any of those three seasons, the Bulls will finally receive the first-round pick. If not, it converts to two second-rounders after 2028.

It doesn’t matter whether the Trail Blazers earn a top-six seed or just barely make it in through the play-in tournament; all that matters is that Portland plays its way into postseason basketball.

How the pick can help the Bulls

If and when the Bulls receive a first-rounder from the Trail Blazers, it will give the front office a level of flexibility it hasn’t had in years. In fact, this potential pick is the only first-rounder the current front office has acquired since taking over in 2020 (excluding the removal of protections on their own pick sent to San Antonio in the DeMar DeRozan trade).

Whether it’s used to draft a prospect of their own or included in a future trade will probably depend on how far along in the “rebuild” the Bulls are, but either way, it’s better than waiting another three years for two second-round picks that would likely be flipped for cash considerations.

Lillard’s return won’t transform Portland overnight, but it gives the Bulls a real chance to finally cash in on a long-awaited asset. For a team held back by limited flexibility, even one first-round pick could push the Chicago Bulls further in the right direction.