4 Biggest Questions Facing the Chicago Bulls This Offseason

The news cycle has spun so fast that Chicago Bulls fans already have whiplash. Alas, it's time to grab a heating pad and take some aspirin, folks! The offseason is only just getting started.

As we inch closer to a massive May 10th NBA Draft Lottery, the pressure on the organization will only build. The time is now to turn a corner and finally put the organization on a more competitive path. With that in mind, let's go over the four most important questions for the franchise to answer over the next few months.

Who is the Next Front Office Leader?

Apr 22, 2022; Chicago, Illinois, USA; Chicago Bulls executive vice president of basketball operations Arturas Karnisovas (right) talks with general manager Marc Eversley (left) before game three of the first round for the 2022 NBA playoffs against the Milwaukee Bucks at United Center. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

Starting off with a real shocker, huh?

Look, I'll be the first to recognize that this is a painfully obvious question, but we can't do this post without asking it. Who the Chicago Bulls choose to replace Arturas Karnisovas will be one of the most important decisions they make in franchise history. As dramatic as that may sound, it's undeniably true, specifically when we consider how loyal this ownership group has been in the past.

Indeed, this will be only the THIRD time since Jerry Krause took over the Bulls in the mid-80s that the Reinsdorfs have hired a new head of basketball operations. Might the fact that they chose to move on from Karnisovas after six seasons imply that they will have a shorter leash in the future? Perhaps, but they still gave the former exec a longer runway than others would.

Let's also not forget the extremely advantageous position the team finds itself in. To Karnisovas' rare credit, he cleaned up his horrendous mess over the last year-plus. The Bulls have significantly more resources than most organizations in the NBA, including all their first-round picks (plus an extra in the 2026 draft), maximum cap space, and a slew of open roster spots. The decisions that are made this summer can and will impact the Bulls immensely moving forward.

So, yes, this might be a big fat "duh" of a question, but it's the most important one by far.

What Type of Coach Will They Hire?

Apr 9, 2026; Washington, District of Columbia, USA; Chicago Bulls head coach Billy Donovan gestures to his team from the bench Washington Wizards in the first half at Capital One Arena. Mandatory Credit: Geoff Burke-Imagn Images | Geoff Burke-Imagn Images

Rather than ponder specifically who the Chicago Bulls will hire as their next head coach, I think a much better question is what kind of coach will a new front office pursue? Aside from perhaps a second in command, this will likely be the first major move that a new lead executive makes. And it should tell us a lot about how they want to run things right off the bat.

Conventional wisdom tells us that they will look for a developmental leader. This is typically a young, up-and-coming assistant who is getting his first taste of what it's like to sit in the lead chair. Minnesota's Micah Nori fits that bill perfectly, as does someone like Miami's Chris Quinn or San Antonio's Sean Sweeney. Going this young and fresh likely signifies that a full-blown rebuild is in the cards.

Another option could be going after someone like Taylor Jenkins, James Borrego, or Jahmal Mosley (assuming he is not retained by the Magic). Still on the younger side, those are three coaches who have past head coach experience with a young group. Could they be willing to take on a long-term project? Sure, but hiring someone like this likely suggests that a new executive has a shorter window in mind. While this might not mean they are planning to go out and hunt a star, it could mean they are open to it in the very near future.

The third option is the win-now swing. We're talking targeting coaches like Mike Budenholzer, Terry Stotts, Frank Vogel, or dare I say ... Steve Kerr!? To be clear, I highly doubt this is the direction a new front office would go, but there is no denying that even interviewing these veteran leaders would tell us a lot about their plans. You don't go this route unless you are considering a quick turnaround. And, technically, the Bulls do have the assets needed to make an aggressive push for a quick fix.

Is Josh Giddey Still A Piece of the Puzzle?

Apr 3, 2026; New York, New York, USA; Chicago Bulls guard Josh Giddey (3) warms up prior to the game against the New York Knicks at Madison Square Garden. Mandatory Credit: Wendell Cruz-Imagn Images | Wendell Cruz-Imagn Images

I'm not sure if everyone would put this on their list of Top 4 questions, but it's something that has entered my mind more than once since The Great Front Office Purge of 2026.

To be absolutely clear, no, I do not believe new leadership will come in and immediately look to move on from Josh Giddey. He will be part of the plans for 2026-27 ... but how big a part? And will he continue to be for the foreseeable future?

Of course, Giddey could quickly fight his way onto the new front office's good side. There is no denying he is an elite passer and has improved significantly as a three-point threat. At the same time, valid concerns remain about his ability to be a consistently efficient downhill scorer and self-creator off the bounce.

Arturas Karnisovas viewed Giddey as a key building block, wanting to center the offense around his pass-first and transition-centric play style. Not only is it unclear if a new front office would have a similar on-court vision, but Giddey has been a very polarizing player in the past. Some seem to believe the 23-year-old still has the potential to be an All-Star-caliber lead guard. Others seem to believe he is destined to be the fourth or fifth-best player on a true contender.

Which end of the spectrum will the new lead exec land on? The answer to that will go a long way toward telling fans how close this front office believes the Bulls are to contention. Giddey is either a core piece or merely a piece. All things considered, his $25 million AAV isn't that hard to move off of, and he is the kind of young player who could be a key trade chip in a superstar-level trade.

How Do You Spend All That Money?

As things currently stand, the Chicago Bulls are positioned to have as much money as anyone in the NBA. They are expected to have six open roster spots and could push that number to as high as seven if they choose not to pick up the option for Leonard Miller (though, I do expect a new front office to keep him around).

Josh Giddey will be their highest-paid player and owed only $25.0 million in 2026-27. In today's NBA, if that's your top cap hit, you're in a very comfortable place. The only real eyesore for a new front office to take on will be Patrick Williams' contract. The forward is owed $18.0 million for the next two seasons and has a player option for that same total come 2028-29. I'm not sure anyone would be shocked if the next hire attempts to get off that salary in the near future.

Regardless, the Bulls' immense financial flexibility is a big reason why this job is as attractive as it is. This allows for a new hire to come in and very quickly make this roster their own. If they wanted to go after a disgruntled, high-budget start, they could make that work easily. If they wanted to play the long game and punt their spending power down the road as they prioritize the draft, they could do that too.

With that said, the latter strategy should coincide with becoming a dumping ground for other teams. We have seen a handful of successful rebuilds begin by using clean books to absorb bad salary in exchange for additional assets. The Bulls are in a perfect position to be that go-to trade team with contenders.

They also have enough money to do this while still going after a restricted free agent or two. Young players like Tari Eason, Walker Kessler, Bennedict Mathurin, or Mark Williams might all be gettable, and each would fill a clear position of need for this Bulls roster. Even if each current team has plans to re-sign them, Chicago has the kind of money to put real pressure on them.

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