Chicago has seen this movie before.
Back in 1987, the city’s sports scene had three towering names driving the conversation at once: Michael Jordan with the Bulls, Andre Dawson with the Cubs and Walter Payton with the Bears. Dawson arrived in Chicago as a free agent for the 1987 MLB season and then turned in a huge individual year, winning National League Most Valuable Player honors even though the Cubs finished 76-85 and missed the postseason.
Jordan was in the middle of his first signature Bulls campaign in 1987-88, the season he won both NBA MVP and NBA Defensive Player of the Year. Payton, meanwhile, was playing his final NFL season with the Bears and saw it end with a divisional-round loss to the eventual Super Bowl XXII champion Washington Redskins.
Even so, Payton had already locked in his place as a Chicago icon after helping the 1985 Bears win Super Bowl XX.
That era even produced a famous winter 1988 photoshoot featuring Dawson, Jordan and Payton, with the image later landing on the cover of the March-April 1988 issue of Chicago Time Magazine.
Now, nearly four decades later, the city is getting another glimpse of that kind of crossover star power.
Bulls wing tandem Matas Buzelis and Caleb Wilson are beginning to put themselves in the middle of Chicago’s sports conversation, and they were front and center Thursday at a Chicago Cubs game alongside Bears starting quarterback Caleb Williams. The trio was photographed in the front row cheering on Cubs center fielder Pete Crow-Armstrong, who is an NL MVP candidate.
For Bulls fans, the bigger point is the possibility. Since Jimmy Butler was traded during the 2017 NBA offseason, the franchise has rarely had much sustained relevance, and it has been even rarer to see a strong Bulls team, a strong Bears team and a strong Cubs team all running at the same time. There is still a long way to go before Chicago basketball is back in a serious way, but if Buzelis and Wilson develop into a true top-end duo, the Bulls could start to look like the kind of team that once anchored the city’s sports identity.
What makes that hope feel a little more real is how visible both players have already been around Chicago. That matters in a city that remembers what it looked like when its biggest names belonged everywhere at once.
In Other News...
Nic Claxton Just Raised The Stakes For The Bulls Next Big Decision
The Bulls offseason move for Nic Claxton was about more than plugging a hole at center. Chicago brought him over from Brooklyn to stabilize a position that has been unsettled, and the contract they inherited gives the front office some flexibility while it figures out what the long-term plan actually looks like. Claxton should get every chance to establish himself as part of the solution, especially with the Bulls still sorting through how to build a sturdier frontcourt.
But flexibility cuts both ways, and that is what makes Claxton such a fascinating piece of this puzzle. If he performs like a dependable starting center, the Bulls can talk about keeping him around longer. If the fit is merely solid and the team keeps looking ahead for bigger swings in the draft, he also becomes the kind of movable asset contenders covet. For Chicago, the next stretch is about more than just Claxtons production. It is about deciding whether he is the answer, or the bridge to the next one. [Read more 🡒]
Bulls Rookie Guards Could Force A Bigger Rotation Debate
With the Bulls set to open the 2026-27 regular season on Oct. 21, the focus around their backcourt has started to shift toward two rookie guards who could make the rotation discussion more complicated than expected. Dailyn Swain and Jaylin Sellers are both worth tracking as the season approaches, not just because of where they fit on the roster, but because their development could influence how much room there is for the veterans ahead of them.
Swain projects as a reserve option who can grow into a steadier role over time, while Sellers brings a different kind of intrigue as a potential scoring spark if he earns meaningful minutes. Chicago does not need either rookie to carry a heavy load right away, but the kind of early progress they show could determine whether the Bulls keep things tight or start pushing for a larger, more flexible guard rotation. [Read more 🡒]
Bulls Rebuild Could Hinge On A Wild Orlando Gamble
A speculative new path for the Bulls has them looking far beyond the usual rebuild talk, and it starts with Orlando forward Paolo Banchero. The idea rests on Chicago chasing a bigger swing than a standard roster shuffle, with Bancheros scoring profile and the Magics recent postseason frustrations making him a name worth monitoring if the Bulls decide to reshape the next phase of the roster.
The fit is where the whole concept gets tricky. Banchero has had real shooting challenges, and any move would force Chicago to think hard about how to maximize his value next to its current pieces, especially with his contract situation adding another layer to Orlandos decision-making. For the Bulls, it is the kind of ambitious gamble that can sound far-fetched at first and still feel like the sort of deal a rebuilding team has to at least explore. [Read more 🡒]