Only four different NBA franchises have won at least six championships. The Los Angeles Lakers and Boston Celtics each have 17 titles, the Golden State Warriors won their seventh title in 2022 and the Chicago Bulls won six titles during the 1990s. With Michael Jordan leading the way, the Bulls were the greatest team of the decade and some may call them the greatest team in league history.

Since their last title run in 1998 though, infamously called “The Last Dance” season, the Bulls have made the playoffs plenty of times, yet they've only made the Eastern Conference Finals once in 2011. The last six seasons have not been kind to this Bulls franchise, as they have just one playoff appearance in 2022 and have not won a playoff series since 2015.

Some of this has to do with bad luck and injuries, especially in the case of Derrick Rose and the team that made the conference finals, but one could make the argument that this team has been set up for disappointment time and time again by those making all of the decisions.

This offseason, the Bulls were faced with multiple questions to answer regarding the futures of Zach LaVine, DeMar DeRozan and Nikola Vucevic, as well as young free agents such as Coby White and recent second-round pick Ayo Dosunmu.

So far, nothing has come of trade rumors surrounding DeRozan and LaVine, Vucevic and White both re-signed with the team on new three-year deals and Dosunmu recently put pen to paper on a three-year, $21 million contract of his own after finding himself as one of the better free agents remaining late in the offseason. In the wake of Lonzo Ball's ongoing knee problems, the Bulls also signed Jevon Carter and Torrey Craig.

These all seem like the right moves for the Bulls, as they couldn't afford to lose any of their core pieces, but what did Chicago actually achieve here?

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The Bulls don't pay taxes

Ayo Dosunmu, Chicago Bulls

Re-signing Dosunmu was the team's latest move. After this transaction, the Bulls find themselves dangerously close to the tax line for the upcoming season. In fact, they are about $3.4 million shy of the tax line right now when looking at guaranteed money on the books, per Spotrac.

When you look at the history of this franchise and what the Bulls have done time and time again, it is clear to see that management and especially ownership do not want to go above and beyond to field a competitive team. Even going back to their championship teams in the '90s, there were plenty of problems regarding Chicago's ownership not wanting to pay players like Scottie Pippen and others.

The Bulls have exceeded the luxury tax threshold only two times in their franchise's history. When they have gone over this number, it has not been by much ($8.1 million total). They were slated to pay the tax for the 2013-14 season when Rose suffered a season-ending knee injury. The team responded to their chances of competing for a title exiting by trading forward Luol Deng in order to get below the tax line for that season.

Paying their way to a championship just is not in the nature of the Bulls franchise, regardless of how much fans beg Jerry Reinsdorf the organization to spend money for impactful players.

The NBA has changed through the years and those who have been willing to spend money on big name free agents and pay a lot in taxes have been successful in their championship pursuit. Just look at what the Golden State Warriors have been able to achieve with their latest dynasty.

Maybe the new CBA agreement coming into play will balance things out, especially with harsh penalties being put on teams who surpass the new second tax apron, but the bottom line is that the Bulls typically do whatever they can to avoid the luxury tax.

Bulls' outlook heading into 2023-24 season

On the surface, the Bulls have the foundation to be a very solid team heading into the new season. LaVine, DeRozan and Vucevic accounted for over 55 percent of the team's production this past year, which is not surprising seeing as they are the faces of the franchise.

However, this organization's bench struggles have been prominent, as Chicago's three stars have received little to no production from anyone else. Maybe the new secondary pieces in Carter and Craig can help change their recent misfortunes, along with the development of young players like White, Dosunmu and Patrick Williams, but the problem that still exists with the Bulls is the fact that they will spend just a little bit more every offseason to ensure that they are a real championship threat.

After missing the playoffs and teams wondering if they would rebuild this offseason, nobody is believing that Chicago will be able to turn things around and suddenly become some kind of real threat in the Eastern Conference. The Bulls themselves may believe this, but when evaluating this team, it is clear to see that they are still missing something.

Ball's injury has really impacted their chances at finding success. If the Bulls truly want to maximize their potential this season, they will utilize the $10.2 million disabled player exception they have received and dip into the luxury tax. They also still do have about half of their mid-level exception remaining worth a little over $6 million and the $4.5 million bi-annual exception, though they are hard-capped at the apron that sits at just over $172 million. Still, Chicago has ways to add money to this roster.

You need star players to contend for a championship, but you also need valuable secondary pieces. The Bulls do not have these players outside of LaVine, DeRozan and Vucevic, which is why it is necessary to pull off a somewhat big move – say, one of the better free agents still available at this point like Kelly Oubre Jr. or Christian Wood? Adding one of these players using their exception pushes Chicago into the tax, yet it also increases their chances to win right now, that is if management and ownership still believe in the trio they have assembled.

The 2023-24 season is going to be a big year for the Bulls, as the franchise currently finds themselves at a crossroads. Regardless of if they find success early on in the season and regardless of if they choose to go through a full-blown rebuild at some point, the one safe bet that remains is that this team will not spend a lot of money to find success.