Damian Lillard Is "Not Interested In Rebuilding," And The Bulls Can Capitalize

Damian Lillard has always been outspoken about his desire to finish his career in Portland. What he hasn't been so vocal about until recently is that he will not partake in a rebuild, which may change his wish to retire a Trail Blazer. Slated to finish 13th in the Western Conference for the second consecutive season, with a combined record of 58-95, it would seem he's in the midst of one right now. Without any marquee signings or blockbuster trades, he may be headed elsewhere to compete for an NBA title. If that's the case, the Chicago Bulls should pick up the phone and not put it down until they complete a deal.

Generational Talent

Needless to say, Damian Lillard is one of the best players of this generation and has a boatload of accolades to show for it. Recently named to the NBA's Top 75 team, he's also got seven All-Star nods and six All-NBA awards and is widely considered one of the best two Trail Blazers of all time alongside Clyde Drexler. His impact on the Bulls would catapult them to an instant championship contender.

His disinterest in a rebuild doesn't come as a shock. Still, with the team having not made it out of the first round of the Western Conference playoffs in five seasons, it may create some urgency for Portland to either ship him for future assets or pursue a second superstar much more aggressively than they ever have during Lillard's tenure.

The Cost Of Contention

This deal would force the Bulls to part ways with Zach LaVine. He would be the deal's centerpiece as the youngest of their stars and the most comparable skill-wise. At five years younger than Lillard but levels beneath him talent-wise, it would take a few more assets. Here's the mock deal, as confirmed possible by the Fanspo trade machine.

Portland Trail Blazers Receive: Zach LaVine, Lonzo Ball, 2027 First-Round Pick (CHI)(Protected Top-Five)

Chicago Bulls Receive: Damian Lillard

The 2023-24 Chicago Bulls

The glaring concern with this move is that it buries Chicago even deeper in the 'lack of future assets' hole but also puts them in the upper echelon of the Eastern Conference. Moving forward, they'd have one of the best point guards in the league and virtually the same roster as this season that ranks top-five in defensive rating, less LaVine, which won't hurt that end of the floor.

The elephant in the room is that retaining Nikola Vucevic, extending DeMar DeRozan, and bringing in Lillard would leave the Bulls with their big three each at least 32 years old, meaning the collapse would leave the franchise in ruins a few years down the road. Is it worth it for a legitimate title shot? Seeing that the Bulls have not been to an Eastern Conference Finals in over a decade and their last Finals appearance was 25 years ago, many would say so. Today's NBA has become one where selling the farm for a win-now team is the most surefire way to contend. Look to the Los Angeles Lakers or Phoenix Suns for examples of what Chicago could be the next to pull off.

Without any championship pedigree on the roster and aging stars DeRozan and Vucevic likely leaving if this team doesn't make significant strides toward contention, going all in on Damian Lillard at the expense of the future is the Bulls' only shot at a championship banner in the next five years. This would give a 2-4 year championship window that hasn't been present in Chicago since prime Derrick Rose's years when even then, they only made the Eastern Conference finals once.

Is it time to make a boom or bust blockbuster deal for Damian Lillard?