Michael Jordan marked a before and after in the city of Chicago, and sometimes the full extent of his impact does not seem as clear as it really was. The NBA legend not only won six championships with the Bulls during the 1990s, but also turned the city into a global and cultural phenomenon.
Haley Cavinder and Claire Kittle send playful message to their NFL partners before SI Swim show
Many believe Jordan also helped change the way Chicago was perceived around the world. The city had long been associated with a negative reputation and gangster stereotypes, with figures such as Al Capone often part of that image. Jordan’s competitiveness and iconic status gave Chicago a sense of pride that the city has not experienced in some time. That could now be changing.

The Chicago Bulls Michael Jordan celebrates after the Bulls beat the Phoenix Suns 99-98 to win their third consecutive NBA title in Phoenix
A photo that captured Chicago’s new generation
One photo was enough to bring that feeling back for those who believe the city could once again have globally recognized sports celebrities like Michael Jordan. It also carried a simple message: Chicago is in good hands.
The photo featured Chicago Cubs center fielder Pete Crow-Armstrong, Chicago Bulls small forward Matas Buzelis, and in the middle, Bears quarterback Caleb Williams — the player carrying the hopes and dreams of an entire city on his shoulders.

Chicago Bears quarterback Caleb Williams, second from left, Chicago Bulls players Caleb Wilson, left, and Matas Buzelis, right, along with music video director Cole Bennett, second from right, celebrate after the Chicago Cubs defeated the Milwaukee Brewers in a baseball game in Chicago
Williams’ personality is magnetic, and he has shown a special connection to the city while earning the support of its fans. He has already given Chicago Bears fans the kind of hope they had not experienced in decades. If he can keep the reigning NFC North champion Bears on their current trajectory, immortality awaits.
Williams is saying all the right things
The reality is that Williams is saying and doing the right things to endear himself to Chicago. If he can lead the Bears back into the playoffs, he could receive standing ovations by the entire city.
But surpassing what Michael Jordan meant to Chicago is a difficult task. Even reaching a point where he is considered that important to the city would be a major achievement.
So why is Williams creating this sense of hope in Chicago? His numbers, personality and statistics are all contributing to that feeling. Williams set the franchise’s single-season passing record with 3,942 yards, while also making it clear that he wants to stay in Chicago for the long term, saying that being in one place until he is done is one of his goals and that he plans to be here.
That sense of belonging is already there. Williams has given Bears fans the kind of hope they had not had in decades, and if he can keep the reigning NFC North champions moving in their current direction, his place in Chicago sports history could grow quickly.
Nobody loves a hometown hero quite like Chicago.