There was a time in Chicago sports history -1987 specifically- when the Chicago Bulls, Chicago Cubs, and Chicago Bears were simultaneously headlined by powerhouse stars: the Chicago Bulls' Michael Jordan, the Chicago Cubs’ Andre Dawson, and the Chicago Bears’ Walter Payton.
Andre Dawson moved to the Cubs as a free agent for the 1987 Major League Baseball season. Dawson went on an improbable yet prolific run during the Cubs' 1987 season to capture the National League Most Valuable Player award, despite the Cubs finishing with a 76-85 record and missing the Major League Baseball postseason.
At the same time, Michael Jordan embarked on what would be his first career-defining Bulls season, the 1987-88 NBA season in which Jordan captured both the NBA Most Valuable Player and NBA Defensive Player of the Year awards.
Walter Payton, the elder statesman of the star trio, played in his final NFL season with the Bears during the 1987 NFL season. Payton and the Bears suffered a divisional round defeat to the eventual Super Bowl XXII champion Washington Redskins.
Despite the sour ending to Payton’s NFL career, he was already forever cemented as an all-time Chicago sports hero as a member of the 1985 Super Bowl XX champion Bears roster.
Chicago's finest: Michael Jordan, Walter Payton and Andre Dawson. pic.twitter.com/KPpJWcRudT
— Paul Knepper (@paulieknep) December 21, 2023
Dawson, Jordan, and Payton gathered in the winter of 1988 to participate in a photoshoot that produced an iconic photograph that appeared on the cover of the March-April 1988 issue of Chicago Time Magazine.
Fast forward to 2026, and the Bulls wing tandem of Matas Buzelis and Caleb Wilson are doing their part to restore the collective sports star power in the city of Chicago that once held a firm hold on the sports zeitgeist of the late 1980s.
— Chicago Cubs (@Cubs) September 4, 2026
Buzelis, Wilson, and Chicago Bears starting quarterback Caleb Williams were photographed in the front row at Thursday’s Chicago Cubs game, cheering on Cubs center fielder and National League Most Valuable Player candidate Pete Crow-Armstrong.
Optimism for Chicago Bulls greatness
Great, relevant Bulls teams have been sparse since Jimmy Butler was traded during the 2017 NBA offseason. Even more of a sparse experience has been a great Bulls team running in parallel with a great Bears team and a great Cubs team.
A tremendous amount of work and roster change will have to occur before the Bulls return to winning ways and national relevance in the NBA. Yet, there is reason for Bulls fans to be optimistic about the Bulls returning to glory if Buzelis and Wilson find their stride as the Bulls' next great duo, like Scottie Pippen and Michael Jordan, or Derrick Rose and Joakim Noah.
The optimism should be underscored by how visible Wilson and Buzelis have made themselves around the city of Chicago.
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