Portland's Trade Deadline Plan Could be a Big Win for the Chicago Bulls

The Chicago Bulls will be diehard Portland Trail Blazers fans over the next few weeks.

Currently holding a record of 10-16, the Trail Blazers sit 11th in the Western Conference. Despite a similar start to Chicago this season, Portland's situation remains a lot different. They have committed rather heavily to a rebuild over the last handful of years, building up lottery-level talent and acquiring several interesting young players. This season, however, they finally decided it was time to take a step forward.

The organization surprised everyone when it acquired Jrue Holiday from the Boston Celtics. Additionally, they went on to re-sign a rehabbing Damian Lillard to a multi-year deal. The moves suggest that the franchise is ready to push its young group forward and re-enter the competitive mix. While their immediate results have remained somewhat underwhelming, it sure sounds like this remains the plan as they head toward the NBA trade deadline.

Michael Scotto of HoopsHype shared tons of NBA rumors in his latest intel article. To be sure, he didn't include anything specific about the Chicago Bulls, but he did mention what the Trail Blazers could be up to in the coming months. And this could have a significant impact on a Bulls team that happens to own a certain first-round pick ...

"Multiple executives have also circled the Portland Trail Blazers as a potential buyer ahead of the trade deadline and among the teams that like Murphy around the league. Some executives around the league who’ve spoken with HoopsHype have also wondered aloud if it would take a package similar to the Desmond Bane trade to acquire Murphy, who’s only 25 years old and signed through the 2028-29 season," Scotto wrote for HoopsHype.

For those who may not recall, the Trail Blazers currently owe the Bulls a lottery-protected first-round pick. They sent Chicago this selection as part of the three-team trade that moved Lauri Markkanen to Cleveland. Of course, the pick has yet to convey with Portland in full rebuild mode, but the Bulls still have a couple more seasons to cash in.

Indeed, Chicago has access to this first-rounder up until 2028. If the Trail Blazers still fail to make the postseason by then, it will turn into a second-round pick. So while the good news is the Bulls still have some time to end up with the extra pick, there is no question they would like to have that in their pocket sooner rather than later.

Chicago Bulls playing the Portland Trail Blazer — Nov 19, 2025; Portland, Oregon, USA; Portland Trail Blazers center Donovan Clingan (23) tries to pass the ball while on the floor as Chicago Bulls guard Ayo Dosunmu (11, right) and guard Josh Giddey (3, behind) apply pressure during the second half at Moda Center. Mandatory Credit: Soobum Im-Imagn Images | Soobum Im-Imagn Images

This feels especially true as they face another organizational crossroad. Many signs indicate that they should do something drastic at the deadline, as they have seven players who are expected to hit free agency this offseason. Entering sell mode now could put them in a prime position to end up with a high draft pick in what many view as a tantalizing and deep draft class. Portland's aggressiveness could then mean they have a chance to pair one high-upside youngster with another first-round talent, which could really jumpstart a rebuild.

Heck, even if the Bulls wanted to go the opposite direction and make a run at a disgruntled star, this news from Scotto feels important. The more eager Portland is to make the postseason, the more likely it is that they give up the first-round pick. This makes the asset feel considerably more valuable in the trade market.

Let's also not forget that the Bulls currently have full control over all their future first-rounders. This isn't something that many teams can say, and the fact that they have an extra pick to play with means they could avoid having to use more of their own in a potential big trade. That's not nothing.

At the end of the day, a lot still has to go right for the Trail Blazers to dodge the lottery this season and fork over their pick. The Western Conference is a bloodbath, and their 10-16 start clearly leaves something to be desired. At the same time, the mere fact that they appear ready to push for the postseason can not be ignored, particularly if you're the seemingly hopeless Chicago Bulls.

May I interest you in a durable Nikola Vucevic, Portland? How about a sharpshooting Kevin Huerter or a fiesty Ayo Dosunmu? Let us know how the Bulls can help make your playoff dreams come true!