No Chicago Bears player had ever made the cover of Madden. Roberto Garza technically did, but that was the Latino version. To think Caleb Williams, a quarterback, the position that has haunted the franchise for decades, was the one to finally do it is nothing short of miraculous. No doubt it was a controversial decision. Williams didn’t win the MVP or even make the Pro Bowl last season. He had the lowest completion percentage in the league. Many feel he was undeserving of the honor.
So how could the Madden creators at Electronic Arts justify such a decision? Their marketing strategist laid it out with an explanation. It stems from the long list of critical moments that led Williams to Chicago, and then the many more moments he engineered last season to get them to the playoffs.
“Caleb Williams is what a true face of the franchise looks like — the culmination of many moments in the Chicago Bears’ incredible history that has led them to their electric, generational quarterback. Madden NFL 27 aims to put more of those critical moments and key management decisions, with meaningful consequences that echo across the NFL, in the hands of our players so that they can build a league that’s truly their own. Just like Caleb, the future of football in ‘Madden NFL 27’ is thrilling and more dynamic than ever before.”
It’s hard to argue with that. Three of the top plays of the 2026 season, according to the NFL itself, were authored by Williams. One of them was his now-famous 4th and 8 throw to Rome Odunze against the Green Bay Packers. The play in which he created the Jumpman motion. Williams explained on the New Heights podcast that he pushed to make that the cover for Madden, believing it was the perfect homage to the greatest Chicago icon of all: Michael Jordan.
Caleb Williams remains as dedicated to Chicago as ever.
Make no mistake, a big part of this was business-motivated. Not long after that incredible throw to Odunze in the playoffs, outlines of the Jumpman pose started surfacing online. Williams moved quickly to trademark it. Getting it on the Madden cover is a brilliant way for him to capitalize financially. The same goes for his “Iceman” pose, which is being used for the Deluxe edition. Nobody can argue the kid has a savvy business sense well beyond his years, no doubt thanks to an education from his father, Carl.
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That said, his comments about honoring Jordan’s all-time photo were genuine. Williams has made it his mission to embrace Chicago as his home and the city he wants to represent. You can see it in many ways. You’ll often find him out on the town, attending Bulls, Blackhawks, and Cubs games. He’s friends with Pete Crow-Armstrong and Matas Buzelis. Best of all, he has fully embraced the rivalry with the Green Bay Packers, trolling them at every possible opportunity.
Williams has one big challenge ahead of him now.
He has to back up his words. Getting on the Madden cover is a tremendous honor. Proving that he deserves it is on the agenda for 2026. People talk about the Madden curse all the time. More than anything, it comes down to whether players can prove they are worth the hype. Patrick Mahomes, Tom Brady, and Calvin Johnson all did. If Caleb Williams wants to put himself in that conversation, he can’t let last season be a fluke. He needs to improve on what he accomplished, ascending to the superstar status the cover represents.
Expectations are high. It’s his second year in Ben Johnson’s offense. He is surrounded by a talented group of weapons. All the elements are there for a big season. He’ll have to do it against a first place schedule, led by a loaded division. In truth, Williams wouldn’t have it any other way. He wants to be challenged. He wants to be the best. If he has to go through lots of good teams to do it, all the better. Just like Jordan, he isn’t afraid of anybody or anything.
