Since entering the league, Damian Lillard has made his intentions clear that he wants to remain with the Portland Trail Blazers his entire career. While he has seen his All-Star peers continuously change teams over the past few years, Lillard has kept his stance on remaining with the franchise that drafted him. After readjusting their roster around Lillard again, the Blazers find themselves with the 13th seed in the western conference. It might be time for the Blazers to shift their focus on their young star Anfernee Simons and bring in pieces to build around his talents.

Lillard is 32 years old and is locked into a contract until 2027. To makes matters complicated, he is owed more than $215 million over the next four years. It’s hard for any team, including the Blazers, to justify paying a 36-year-old Lillard $63 million in the final year of his contract. If a team decides to trade for Lillard, they must be confident they can win a title within the first three years of his deal, making it easier to eat the cost of the final season of his contract.

The Bulls are stuck in NBA purgatory with an aging roster and an injured point guard. It’s hard to depend on Lonzo Ball at all at this point. Even if he returns next year, the Bulls will wait for his following injury to hold their team back. Lonzo Ball and Anfernee Simons are both 25 years old or younger; if the Blazers stay patient and wait for Lonzo Ball to get his body right finally, pairing those guards up in the backcourt could pay dividends in the future.

Thanks to the Minnesota Timberwolves for giving a ridiculous offer for Rudy Gobert, which had seven first-round picks, which include swaps, the trade market has now reset for star players. The Bulls do not have that kind of assets to offer for Dame, nor should they even if they did. The Bulls have a mix of young players around the age of Simons and future draft picks, which should be plenty to put together an enticing offer.

Bulls Trade Package For Lillard

Bulls Trade: Lonzo Ball, Alex Caruso, Patrick Williams, Coby White, Dalen Terry, Protected Portland first-round pick, 2024 first-round pick swap, 2026 first-round pick, 2028 first-round pick

Blazers Trade: Damian Lillard, Gary Payton II, Drew Eubanks

The Bulls will mostly be out of their first-round picks until 2029 after giving away a few to the Magic in exchange for Nikola Vucevic and a 2025 first-round pick to the Spurs when they acquired DeMar DeRozan. They can triple down on that strategy and return the Blazers’ pick to Portland while throwing in a pick swap and two additional picks. That is a bargain deal compared to the Donovan Mitchell, Dejounte Murray, and Rudy Gobert trade. The part that hurts the most is sending away Lonzo Ball, Alex Caruso, Patrick Williams, and Coby White. Both Caruso and White have been in trade rumors for the majority of the year, and Williams has been an underwhelming project since he was drafted. The Bulls would be moving on from Lonzo Ball after he played just 35 games for them in his first two years with the franchise, but as the saying goes: you have to give something to get something.

The Bulls would run a lineup of Damien Lillard, Zach LaVine, DeMar DeRozan, Javonte Green, and Nikola Vucevic without depth. Come playoff time, the best players on the court find themselves playing more than 40 minutes per game anyway, so the Bulls have plenty of justification to put together one last contender push with DeRozan and Vucevic both above the age of 32. If everyone can stay healthy, the Bulls have a legitimate shot at winning the title for another two years. After that, they can focus on rebuilding around a then 29 years old Zach LaVine, which many teams would consider themselves lucky to have that opportunity.