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Why the Chicago Bulls are Trapped

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The Chicago Bulls are trapped — not by injuries, not by bad luck, but by their own indecision. This once-proud franchise has spent the better part of a decade chasing quick fixes instead of committing to a real direction. The result? A team that’s too good to tank, too flawed to contend, and far too stubborn to admit it.

Let’s call it what it is: the Bulls are stuck in NBA purgatory. And the worst part? They did it to themselves.


The downfall didn’t start overnight. It began years ago with the same pattern of overpaying for short-term stability instead of long-term growth. Remember when the Bulls threw big money at Dwyane Wade and Rajon Rondo in 2016, selling fans on a “Three Alphas” era with Jimmy Butler? That team lasted one season and flamed out spectacularly. Then came the Jabari Parker contract — two years, $40 million for a player who couldn’t defend a chair. The front office kept chasing name recognition instead of building an actual foundation.


Even after finally trading Butler in 2017, a move that should’ve triggered a full rebuild, Chicago refused to commit. They drafted decent players — Lauri Markkanen, Wendell Carter Jr., Coby White — but couldn’t develop them into stars because the organization kept flipping the script every two years. Then, in 2021, the front office made its biggest gamble yet: they doubled down on mediocrity by trading for DeMar DeRozan on a $85 million deal and trading for Nikola Vučević the season before, while sending out valuable picks that could’ve been used to rebuild. The plan was clear — skip the rebuild, jump straight to relevance. It worked… for about half a season.


Apr 19, 2024; Miami, Florida, USA; Chicago Bulls forward DeMar DeRozan (11) dribbles the basketball as Miami Heat forward Haywood Highsmith (24) defends in the first quarter during a play-in game of the 2024 NBA playoffs at Kaseya Center. Credit: Sam Navarro-Imagn Images
Apr 19, 2024; Miami, Florida, USA; Chicago Bulls forward DeMar DeRozan (11) dribbles the basketball as Miami Heat forward Haywood Highsmith (24) defends in the first quarter during a play-in game of the 2024 NBA playoffs at Kaseya Center. Credit: Sam Navarro-Imagn Images

That 2021–22 team, led by Zach LaVine, DeRozan and Vučević, was fun. They moved the ball, played hard, and briefly held the top seed in the East. But when injuries hit and defenses adjusted, the Bulls were exposed. Since then, they’ve been the NBA’s definition of average — hovering around .500, flirting with the play-in, and pretending it’s progress.


The contracts haven’t helped. LaVine’s $215 million extension became one of the league’s most immovable deals before he was even traded. Vučević’s three-year, $60 million extension made even less sense for a team clearly not built to win now. And now, DeRozan’s future looms large again, forcing Chicago to choose between re-signing a 35-year-old scorer or letting another asset walk for nothing. No matter what path they pick, it feels like a lose-lose.


Meanwhile, teams that embraced the rebuild — like Indiana, Orlando and Oklahoma City — are thriving. They drafted well, developed young cores and stayed patient. The Bulls, on the other hand, tried to fast-forward through the hard part. They’ve been operating like a franchise scared to be bad, when in reality, being bad for a couple of years might be the only way out of this mess.


It’s not just the contracts — it’s the culture. The Bulls haven’t had a clear identity since Derrick Rose’s MVP season. They’re not an offensive powerhouse. They’re not a defensive juggernaut. They’re a team that exists in the middle, night after night, hoping for something to magically click. And it never does.


The fans know it, too. Chicago isn’t a market that celebrates mediocrity. The city that watched Michael Jordan dominate the ’90s and saw Derrick Rose rise from Englewood to superstardom deserves better than “play-in potential.” Yet year after year, the Bulls front office feeds the same narrative: stay competitive, keep the seats filled, and maybe sneak into the postseason. It’s basketball without ambition.


The Bulls don’t need tweaks — they need transformation. They need to stop handing out loyalty contracts and start stockpiling draft picks. They need to pick a direction, not another patchwork lineup of “solid veterans.” Because right now, Chicago isn’t chasing greatness — they’re clinging to relevance. And in a league built around stars, that’s not just being stuck. That’s being trapped.

Author Name:

Steven Ryan

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