The 2023-24 season could be franchise-altering for the Chicago Bulls in several ways. With depleted cap space and minimal draft capital, Chicago's future direction is foggy at best. Recently inking Nikola Vucevic and Zach LaVine to long-term deals well into their 30s, the anchoring to a duo with such minimal playoff success was head-scratching. DeMar DeRozan will be the next major contributor to hit free agency this summer following his age-34 season, and playing some of the best basketball of his career means his price tag won't be cheap headed into 2024. When assessing which Bulls will have the warmest seats this year, it's essential to establish that this is pressure from an organizational standpoint, not an individual one. DeRozan's is primarily a personal pressure to perform, as it will predominantly relate to the payday he receives this summer. Let's dissect who's got the most to prove this season, and what it could mean if they fall short.
3. History Not On Billy's Side
After Michael Jordan's and Phil Jackson's final title in 1998, the Bulls have stumbled at head coach with one outlier, Tom Thibodeau. Tim Floyd had a winning percentage of 18% across four seasons, failed to reach the postseason in each of those years, and was fired midseason in 2001. Bill Cartwright had a 32% winning percentage across his three seasons before also being canned midseason. After a few quick hitters and Thibodeau's successful tenure, Fred Hoiberg was next to follow the trend. After a 43% winning percentage and only two playoff wins in his lone playoff appearance, he was fired midseason for Jim Boylen. Boylen boasted a 46% winning rate over his season and a half, failed to reach the postseason in each, and was replaced by Donovan in 2020.
After three full seasons, Donovan posts a 49% winning percentage, one playoff appearance, and one lone playoff victory. Despite signing an undisclosed extension for "several years" this past summer, the clock is ticking on Chicago's head coach. A failure to reach the postseason or to develop some of these failing draft selections could quickly result in his dismissal, similar to his predecessors.
2. LaVine's Hefty Trade Value
Zach LaVine is the player with the most pressure, primarily due to being one of the few with significant trade value. If Chicago's season looks similar to last, don't be surprised by an all-out firesale at the trade deadline, including LaVine's lucrative contract being shipped off. A package slightly smaller than the ones for Rudy Gobert, Donovan Mitchell, Damian Lillard, or Jrue Holiday would put the Bulls in prime rebuild position with draft capitals or young talent alike. While LaVine's second half last season was much better than his start, he still failed to receive a single All-Star vote, has one playoff appearance and victory to his name, and has never been selected to an All-NBA team. As a top-20 most expensive contract leaguewide, the Bulls would likely absorb some of his deal to get most of his contract off the books to a contending roster.
As Patrick Williams echoed alongside much of the roster when asked about various questions, "Winning cures all." Leading a playoff team would protect LaVine's spot in Chicago, but it's pretty far-fetched with a similar lineup to last season's disappointing finish.
1. AK's Last Chance
Arturas Karnisovas has to be under the most pressure heading into this season. Preparing to embark on his fourth year with the majority control of Chicago's personnel and roster changes, draft capital, and cap space, Karnisovas has been underwhelming for the most part. He's done little to nothing of value to the franchise except for possibly the best free agency signing in the past decade for the Bulls, DeMar DeRozan. Assessing how the Bulls' draft selections have shaken out is a deep dive into mediocrity and wasted capital. Stacking up the free agents and players he's traded for is dicey, and the overall lack of success means someone has to take accountability.
Draft picks since his arrival: Patrick Williams (1st round, 4th overall), Marko Simonovic (2nd round, 44th overall), Ayo Dosunmu (2nd round, 38th overall), Dalen Terry (1st round, 18th overall), Julian Phillips (1st round, 35th overall).
One word to sum up four seasons worth of drafts, including a top-five pick, ouch. Williams is a career nine-point-per-game scorer and role player. Dosunmu is the only other one in the rotation and only averaged 26 minutes a game last season with eight points per contest. Simonovic is no longer on the roster, only seeing 50 minutes across 16 career games. Terry has not seen meaningful time, and Phillips will likely be in the same boat during his rookie campaign. It's not an exaggeration to say he's selected one role player and no other impactful players in his tenure in Chicago, and it is simply unacceptable.
Honorable Mention: Patrick Williams
Barely missing the list, Williams is also under a heap of pressure. While it won't cost him his career, it will almost surely cost him his tenure in Chicago if he performs similarly to his last three seasons. Even though coaches and teammates alike have praised his skill set and potential, it needs to come to fruition at some point.
As a former top-five selection entering the final year of his contract, without proof of being a serviceable NBA starter with star potential, he'll likely be hoping another team is willing to invest in the 22-year-old underwhelming wingman.
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