Being a Chicago Bulls fan hasn’t been easy for most of the past decade. It’s been encompassed by the Derrick Rose injury, his trade out of town, Jimmy Butler’s falling out, the GarPax implosion, and Lonzo Ball’s knee injury. All of that has led to one of the darkest periods in franchise history. They’ve hovered in mediocrity for years, never being taken seriously as a playoff contender, let alone a championship one. Still, fans have held onto hope that a few breaks in the future will get them back into the mix.
One longtime analyst and insider isn’t buying it. Bill Simmons asked a simple question on his podcast. Which team has the worst outlook for the next five years in the NBA? His choice was Chicago. The reasoning was twofold. In his opinion, they don’t have a single good player on their roster. The only argument he’d accept is Matas Buzelis and the young forward is still unproven. Only one path exists out of this quagmire, which is 2026 free agency when the Bulls have multiple big contracts coming off the books.
There is one problem with that. Jerry Reinsdorf never spends big money. In a 2023 survey, the Bulls ranked a distant 24th in luxury tax spending.
Bill Simmons says the Bulls are in the worst position in the NBA for the next 5 years.
Coby White’s next contract could ruin the Bulls trajectory. Either they let him walk or they overpay for a role player. pic.twitter.com/oubu6q7M5R
— Die-Hard Chicago Bulls Fans (@DieHardCBfans) July 7, 2025
The Chicago Bulls have one of two ways out of this.
Either they spend the big money in free agency or pray they get lucky in the draft. This team doesn’t look bad enough to be a contender for the #1 overall pick next year. They could still win the lottery, but that hasn’t been kind to them in recent years. Of course, that didn’t stop Dallas, but anybody with common sense knows that was probably rigged. Free agency is the most logical path. It comes down to who will be available. The top options include Luka Doncic, Paolo Banchero, LeBron James, Trae Young, and Jalen Williams. Only one of those is a legitimate franchise changer, and most believe Doncic will stay in Los Angeles. That means the Chicago Bulls may have to make two big moves to put this team into a winning position. It is hard to imagine Reinsdorf signing off on that.