The Chicago Bulls are one of the most celebrated franchises in NBA history, but it has been a long time since the Michael Jordan glory days. While there finally appeared to be some real promise in the 2021-22 season after some lean years following the Jimmy Butler trade, the Lonzo Ball injury and other issues crashed them back into mediocrity. They finished with a 40-42 record last season, failing to miss the playoffs after blowing a late lead against Butler's Miami Heat in the play-in tournament.

Zach LaVine was a key piece in Chicago's Butler trade and has been with the Bulls for six years now, becoming a face of the franchise alongside DeMar DeRozan and Nikola Vucevic. When the organization made the move to trade for Vucevic in 2021 and sign DeRozan months later in the offseason, they envisioned a new “Big 3” that would challenge the best of the best in the Eastern Conference, possibly leading this franchise back to the Finals with a chance to win their seventh championship.

Instead, after that initial promise, this era for the Bulls with LaVine, DeRozan and Vucevic is full of question marks. Ball has missed the last season and a half and will miss the entire upcoming season. Rumors surrounding LaVine being frustrated appeared in the middle of last season, only for the All-Star to come out and claim that there is nothing abnormal about a team being frustrated after some tough losses.

While there was speculation about Chicago blowing things up, with some LaVine trade rumors playing a role in this, this organization essentially decided to run it back and is still confident in the potential they saw just a couple of years ago. Having a long offseason to rest, reflect and prepare for the 2023-24 season may not have been the worst thing for the Bulls. Whether or not the moves they made this summer can help fulfill this dream is yet to be seen.

Offseason additions and departures

Additions: G Jevon Carter (free agency – MIL), F Torrey Craig (free agency – PHX), F Julian Phillips (draft)

Departures: G Patrick Beverley (free agency – PHI), F Derrick Jones Jr. (free agency – DAL)

In an offseason that was full of spending and new contracts for the Bulls, a vast majority of the money they gave out was to familiar faces. Nikola Vucevic received a three-year, $60 million extension at the end of June, and the team re-signed guards Coby White and Ayo Dosunmu to new three-year contracts in free agency. Forward Terry Taylor also received a new two-year contract, which is non-guaranteed for both seasons.

Starting with Vucevic, the 32-year-old veteran had no desire to leave Chicago, wanting to negotiate a new long-term deal with the organization all season long. Finally, right before free agency began, he got this desired contract. Vucevic is now set to be with the Bulls through the 2025-26 season, that is unless he is traded before then.

In 181 total regular-season games with the Bulls since joining them in 2021, the former All-Star center has averaged 18.2 points and 11.1 rebounds per game. He has played his part well alongside LaVine and DeRozan, which is why the team couldn't afford to make the mistake of not retaining him heading into the summer.

As for White and Dosunmu, their situations were a little different. Seeing as Ball is not going to be around and the Bulls' backcourt has been a mess through the years, it only made sense for them to keep White. The 23-year-old signed a three-year deal worth up to $40 million during the first few hours of free agency, which was a little surprising given that his role and minutes were inconsistent.

Becoming more of a weapon from the perimeter in recent years, White came off the bench in 72 of the 74 games he played in during the 2022-23 season. He was the Bulls' sixth man and was definitely the team's best scoring weapon outside of their three stars.

Dosunmu's new contract came about three weeks after free agency began, as the restricted free agent failed to attract a lot of interest in the open market. After impressing as a rookie, the Chicago native took a bit of a step back in Year 2, but the Bulls didn't want to lose the youngster and kept him around for guard depth.

The key addition in the Bulls' backcourt this offseason was Jevon Carter, a defensive-minded guard who agreed to a three-year contract worth nearly $20 million. Carter made a name for himself with the Milwaukee Bucks the last couple of years, stepping up into their starting unit when Jrue Holiday and Khris Middleton were dealing with injuries. Playing in 81 games last season, the 27-year-old proved to be a durable combo guard who shot 42.1 percent from three-point range.

Out on the wing, the Bulls brought in veteran forward Torrey Craig after he spent the last year and a half with the Phoenix Suns. Craig shot a career-high 39.5 percent from long-range last season and has always been known to be a versatile defender who can wear multiple hats for his team.

Last season, the Bulls ranked 16th in the league in three-point shooting percentage but again finished with the fewest attempts from deep per game. The front office made it a point to address the lack of three-point shooting by adding Carter and Craig, while also looking to maintain a defense that surprisingly finished in the top 10 in defensive rating.

As far as building their roster goes, the Bulls did a really nice job in free agency. Patrick Beverley and Derrick Jones Jr. departing does not impact the team much with Carter and Craig coming in, plus the contracts they agreed to were very reasonable.

Depth hurt this organization during the 2022-23 season. Now, they have a handful of players at every position who can see at least 20 minutes of work on any given night. Of course, LaVine, DeRozan and Vucevic will all play more than 30 minutes per game.

Zach LaVine, DeMar DeRozan trade rumors

Zach LaVine, DeMar DeRozan, Chicago Bulls

Speaking of Zach LaVine and DeMar DeRozan, they remain on the Bulls' roster with training camp right around the corner. Chicago's lackluster performances to end last season drew tons of question marks about the future of this core, especially since other teams in the Eastern Conference are beginning to surpass them.

By sacrificing youthful, high-potential talents such as Lauri Markkanen and Wendell Carter Jr. through the years, the Bulls were able to bring in Nikola Vucevic and DeRozan. The organization has made it clear that they were not going to give up on what they have constructed after two seasons, especially since a combined 86-78 record over this span is not that terrible.

When you look at the team's financial situation and what the future holds, though, a lot of uncertainty presents itself.

LaVine signed a five-year, $215 million contract with the Bulls last offseason and is under contract through the 2025-26 season. He does own a player option at $48.9 million for the 2026-27 season. The Portland Trail Blazers and Philadelphia 76ers were two teams mentioned as possible trade suitors for the two-time All-Star, yet no real offer ever formed. The New York Knicks were another team quietly monitoring LaVine's status in Chicago.

According to Bulls reporter K.C. Johnson, the Bulls were looking for a “good” young player, multiple first-round draft picks and a salary filler in any trade proposal for LaVine. No team in the league was willing to meet this price for the 28-year-old.

As the 2023-24 season approaches, there is still a possibility of LaVine's name coming back up in trade rumors, especially ahead of the 2024 trade deadline. It would be difficult for a team to take on a $40 million contract in the middle of the year, but Chicago could show more willingness to move on from him if they begin to trend down towards the bottom of the Eastern Conference standings.

For DeRozan, much of the same philosophy exists. The team is not actively looking to trade either player, yet they would likely be more inclined to do so if success does not present itself right away. The definition of insanity is doing the same thing over and over again and expecting a different result. Well, the Bulls are now running back the same core for the third straight season and, so far, there has been no different result in the success they've found.

The key difference between LaVine and DeRozan is the fact that the 34-year-old All-Star is in the final year of his contract. With this in mind, DeRozan is set to become an unrestricted free agent next summer should he not receive an extension. His $28.6 million contract is absolutely more obtainable for rival teams compared to LaVine's current deal, plus any championship contender could utilize the six-time All-Star as a rental in any potential trade.

There is still a possibility of the Bulls and DeRozan coming to terms on an extension, as the veteran and the team do appear to have a level of interest in agreeing to a new deal.

“DeMar’s been great. He’s been terrific for this group, not only on the court but off the court,” Bulls GM Marc Eversley stated recently, via The Athletic. “He’s been a leader. I would love DeMar to be part of this program long term. Let’s see how that plays out and what that looks like going forward… He’s been an integral part of this program’s success. We hope he is here long term.”

Chicago has two big decisions to make regarding the futures of LaVine and DeRozan. Going through a long, drawn-out rebuild has never been something this organization has looked to do, which is why it is unlikely that both stars would be moved.

2023-24 season outlook

If there is one team that had to be labeled as the ultimate question mark entering the 2023-24 season, it would have to be the Chicago Bulls. This team should have been so much better than they were a season ago, yet the will to want to fight night after night appeared to vanish.

The trio of LaVine, DeRozan and Vucevic averaged 66.9 points per game last season, making them one of the best offensive threats in the league. Both LaVine and DeRozan also ranked inside the top 20 in the league in scoring, yet the team's three-point shooting problem put them as one of the worst offensive teams in the NBA based on offensive rating.

Should things in Chicago quickly go south to begin the new year and they fail to establish themselves as a true playoff threat, Billy Donovan could wind up being the one to blame. Finishing 10 games above .500 in his first season with the team, Donovan's team did not fight with the same compassion and energy in his second season as the head coach, blowing a lot of leads and losing in frustrating fashion. This is not to say that the Bulls head coach is on the hot seat right now, but his status with the organization is definitely a talking point should improvements not be made.

Patrick Williams is another key talking point heading into the new year, as he will need to step up for the Bulls to make it back to the playoffs. Entering his fourth season in the league, Williams has not yet received an extension from the team this offseason and has yet to come into his own as a reliable complementary option at either forward spot. Chicago remains high on his abilities and is hopeful of a breakout season after taking him fourth overall in 2020.

At the end of the day, everything for the Bulls stills flows through LaVine and DeRozan. This team looked lost at times with one of them not on the floor last year, and where Chicago receives secondary scoring help from still remains a mystery.

Is the Williams leap season coming? Will White build on his success from a season ago off the bench and will Dosunmu improve as an all-around scorer? Will the arrivals of Carter and Craig provide a much-needed lift in terms of perimeter shooting, opening up the offense to attack the basket more?

These are key questions pertaining to this team right now. Until we actually see the Bulls in action, it is hard to truly assess their chances of making it back to the postseason. Their future remains a mystery nonetheless, as failure to succeed will likely lead to the departures of one of their stars.