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Reading: Bulls’ Next Plan Should Be To Acquire 6x All-Defensive Guard To Continue Their Rebuild
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Home > NBA Trade Rumors > Chicago Bulls Trade Rumors > Bulls’ Next Plan Should Be To Acquire 6x All-Defensive Guard To Continue Their Rebuild

Bulls’ Next Plan Should Be To Acquire 6x All-Defensive Guard To Continue Their Rebuild

With Josh Giddey secured, we look at a trade proposal that would allow the Bulls to continue their rebuilding project by acquiring Jrue Holiday.

Siddhant Gupta
Sep 10, 2025
8 Min Read
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Mandatory Credit: Bob DeChiara-Imagn Images

The Chicago Bulls are poised to be a more exciting team in the upcoming season. Having finalized Josh Giddey’s extension, the Bulls have secured a key piece of their core, ensuring that their rebuilding project progresses on the right track.

Contents
  • How Does Holiday Help The Bulls Improve?
  • How Do The Blazers Benefit From This?
  • What Do The Bulls Need Going Forward?

Giddey’s signing does not drastically change the Bulls’ rotation, as the roster is largely similar to what it was last season. But by retaining the star-caliber guard, Chicago has effectively locked in their young core by pairing Coby White and Matas Buzelis with Josh Giddey.

While Chicago will be pleased with this signing, it is evident that they aren’t viewed as a competitive team in the East. Having made very few noteworthy additions to their roster, the Bulls will have to rely on their young players to show significant improvement.

Given that this isn’t sustainable, the organization is better off leveraging some of its young talent to acquire key roster pieces. With the purpose of a rebuild in mind, this article explores a trade scenario that would allow Chicago to acquire a solid veteran guard in Jrue Holiday from the Portland Trail Blazers.

Proposed Trade Details

Chicago Bulls Receive: Jrue Holiday

Portland Trail Blazers Receive: Patrick Williams, Kevin Huerter


How Does Holiday Help The Bulls Improve?

Jrue Holiday has slowly but surely developed a reputation for being one of the best role players in the league. While being a solid guard on offense, Holiday specializes in being a lockdown defender. His ability to contribute on both ends of the floor while making the most of his championship experience could prove to be immensely valuable to the Bulls.

Last season with the Boston Celtics, Holiday averaged 11.1 points, 4.3 rebounds, 3.9 assists, and 1.1 steals per game, while shooting 44.3% from the field and 35.3% from three-point range.

The 35-year-old has proven himself to be a key asset to any team he has been on. With six All-Defensive team selections, he has also earned two All-Star selections over the course of his career. In this regard, Holiday’s resume is enough of a reason to establish that he would be a great addition to Chicago.

Acquiring Holiday would have some implications on the team’s rotation and salary cap. 

At $32.4 million, the two-time All-Star would become the most expensive contract on the Bulls’ payroll. But in the process of acquiring him, the team also parts ways with Patrick Williams ($18.0 million) and Kevin Huerter ($17.9 million), amounting to a total of $35.9 million in outgoing salaries. 

The deal effectively sees the Bulls shed $3.4 million in salary, which may allow them to sign key free agents moving forward. Overall, it facilitates further roster development activities, which would be in Chicago’s best interests.

Holiday’s arrival would also have an impact on the team’s rotation, primarily the starting lineup.

With Williams headed out in this scenario, Holiday would be replacing the forward in the rotation, although in the capacity of a guard. On this note, Giddey’s positional flexibility may prove to be vital.

As Holiday and White share the backcourt, Giddey’s size would allow the Bulls to run with a three-guard lineup without sacrificing on size. With Buzelis and Vucevic then filling out the frontcourt, Chicago would boast a fairly solid rotation.

This move may not transform Chicago into a title contender, but it would make it an attractive destination. With the financial flexibility and space to add more players, the Bulls could proceed with cultivating roster strength.


How Do The Blazers Benefit From This?

The Portland Trail Blazers may not stand to gain as much as the Bulls in this trade, but it still has some merit for them. As a rebuilding team, even with the recent reunion with Damian Lillard, Portland could have used for young players. 

With two vastly different players in Williams and Huerter coming over in this deal, the Blazers could make the most of the situation.

Both Bulls players present some potential to be contributors for the Blazers. Given Portland’s current rotation, they may see more upside in acquiring Huerter than Williams.

Huerter is a 27-year-old sharpshooter. Although he saw a drop-off in performance early in the season with the Sacramento Kings, the guard saw a resurgence in form after joining the Bulls.

With Chicago, he averaged 13.2 points, 3.3 rebounds, and 3.2 assists per game, while shooting 43.9% from the field and 36.7% from three-point range. Having appeared in 69 games last season, the 27-year-old displayed durability. This will be viewed favorably by the Blazers, who saw a lot of key players sustain injuries last year.

Additionally, Huerter is also on an expiring contract. With the opportunity to shed $17.9 million in salary, Portland may be intrigued by this acquisition.

Meanwhile, Williams may draw less interest, primarily due to the nature of his contract. With four years left on his contract and an $18 million cap hit next season, the Blazers may not be as inclined to acquire the forward, but he could still make an impact.

The Bulls saw a lot of potential in the 24-year-old. Although he seems to have plateaued in Chicago, he could show significant improvement in a different environment.

Currently, the Blazers are expected to see Jerami Grant start at the power forward position. Given his reputation as an injury-prone player, Portland would do well to have insurance in the frontcourt if Grant goes down.

Last season, Williams averaged 9.0 points and 3.8 rebounds on 39.7% shooting from the field and 35.3% shooting from the perimeter. With his athleticism, scoring versatility, and two-way potential, the 24-year-old could be considered an investment for the future. But this would require the Blazers to cultivate his talent.

Overall, while Portland may be hesitant to do this deal, adding younger players that fit their timeline could be beneficial, depending on their approach toward rebuilding.


What Do The Bulls Need Going Forward?

Successfully retaining Giddey will have major implications for Chicago’s future. With a gifted guard running the team’s offense, the Bulls are likely to see their scoring production increase.

While this presents an exciting outlook for the future, if the Bulls intend to be competitive, they will need to acquire additional reinforcements, particularly on the defensive front. 

Currently, none of the starters in Chicago, barring Williams and, to some extent, Buzelis, have solid defensive instincts. Addressing this could prove to be a priority in the immediate context.

As things stand, the Bulls still have an opportunity to secure a playoff berth next season. Given the weakened state of the Eastern Conference due to injuries, Chicago has a solid chance if their key players show tangible improvement.

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TAGGED:Chicago Bulls ArchiveJrue HolidayPortland Trail Blazers Archive
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BySiddhant Gupta
Siddhant Gupta is a basketball columnist at Fadeaway World, based out of Mumbai, India. He combines firsthand playing experience with thoughtful analysis to report on the NBA's ever-evolving world. A lifelong athlete, Siddhant's perspective is rooted in years on the court, giving his work a unique edge that resonates with both casual fans and seasoned ones.Before joining Fadeaway World, he spent two formative years at Sportskeeda, where he sharpened his skills and had the opportunity to interview NBA legend Ray Allen during his time in India. A diehard Los Angeles Lakers fan since 2008, Siddhant doesn't just report on the game—he lives it. Beyond his work, he is a student of the game, constantly learning, debating, and engaging with the local and global basketball communities.
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