Chicago Sports are having quite the moment right now. Not only did both the Chicago White Sox and the Chicago Cubs make the MLB postseason for just the fourth time in history, but the Chicago Bears are the reigning NFC North champions, and the Chicago Bulls and Chicago Blackhawks are both buzzing ahead of their seasons starting.
The Bears, in particular, seemed poised to succeed for the next several seasons, as the partnership between young franchise quarterback Caleb Williams and head coach Ben Johnson seems to have the franchise to be perennial contenders in the NFC.
In light of the recent success the Bears have had, employees of Barstool Sports, which has a Chicago office, debated what it would take for Williams’ legacy to surpass that of Bulls legend Michael Jordan, who won six NBA titles with the Bulls and is widely regarded as the greatest basketball player of all time.
“A couple of Bears fans here just said that Caleb Williams would be a bigger Chicago legend if he won one Super Bowl than Michael Jordan. I want to throw up on my d*ck,” Dana Beers posted on X.
PeterFonseca, from the Chicago Sports Bums podcast, said that the answer is three and then suggested that Big Cat, the de facto head of the Chicago office, hire more older employees to remind everyone just how impactful Jordan was during his playing days.
In response, White Sox Dave, another prominent Chicago Barstool personality, weighed in.
3 Super Bowls is the correct take here. If he wins 3, then he’s bigger than MJ in Chicago https://t.co/gK9Fqgpc5z
— whitesoxdave (@barstoolWSD) September 29, 2026
“3 Super Bowls is the correct take here. If he wins 3, then he’s bigger than MJ in Chicago,” Dave posted.
Although three Super Bowls would be quite the accomplishment, and would almost certainly ensure that Williams got a bust in Canton after retiring, it still feels like more would have to happen to leave a bigger impact in the Windy City than Jordan. What do you think Williams would have to accomplish?
About Qwame Skinner
Qwame Skinner has loved both writing and sports his entire life. In addition to his sports coverage at Comeback Media, Qwame writes novels, and his debut; The First Casualty, an adult fantasy, is out now.