Tom Brady, a name synonymous with football greatness, is often associated with his two-decades-long dominance with the New England Patriots and his incredible Super Bowl victory with the Tampa Bay Buccaneers in 2021. However, what many Chicago Bears fans may not know is that they were just a heartbeat away from possibly witnessing the greatest quarterback of all time donning the navy and orange of the Bears. In a recent interview, Brady revealed that, during his free agency in 2020, he was seriously considering joining the Chicago Bears before ultimately signing with the Buccaneers.
This revelation has left Bears fans imagining what could have been. Could Tom Brady have been the missing piece for a franchise long searching for its quarterback messiah? How would the Bears’ fate have changed, and how did it all come so close to happening?
The Decision of a Lifetime: Bears or Buccaneers?
When Tom Brady entered free agency in 2020 after leaving the Patriots, the entire NFL world buzzed with anticipation. At 42 years old, many wondered if the quarterback still had what it took to perform at an elite level outside of the Bill Belichick system. Teams with championship aspirations clamored for Brady’s services, hoping his unparalleled leadership and experience could transform their franchises. While the Buccaneers ultimately won Brady’s signature, the Chicago Bears were right there in the running.
Brady recently shared that the decision to join Tampa Bay wasn’t as clear-cut as many believed. He mentioned that he was back and forth between potential teams, and Chicago, with its desperate need for a franchise quarterback, was on the radar.
For Bears fans, this revelation is both tantalizing and frustrating. For a team that has struggled for decades to find consistency at the quarterback position, the prospect of landing the greatest QB of all time would have been a dream come true. Instead, Chicago’s ongoing quarterback carousel continued while Brady went on to lead the Buccaneers to a Super Bowl title in his first year in Tampa.
Why Chicago Was in the Conversation
While it may seem surprising that Chicago was in the running for Brady, there were several factors that made the Bears an attractive destination. The Bears had just come off an 8-8 season in 2019, and their defense was still among the best in the NFL. Khalil Mack and Akiem Hicks anchored a defensive unit that had the potential to keep games close, which is exactly the kind of situation where a quarterback of Brady’s caliber could thrive.
On the offensive side, the Bears had pieces like wide receiver Allen Robinson, who had emerged as one of the most consistent pass-catchers in the league. Pairing Robinson with Brady’s precise passing abilities could have been the offensive spark Chicago desperately needed. Plus, the idea of bringing the Lombardi Trophy to a storied franchise like the Bears—who hadn’t won a Super Bowl since 1985—could have been an alluring challenge for a competitor like Brady.
Beyond the roster, Chicago’s rich sports culture and large market were also appealing factors. Brady’s legacy in New England was already cemented, but joining the Bears would have given him the opportunity to revive one of the NFL’s most historic franchises, elevating his GOAT status even further. It’s easy to see why Brady gave serious thought to playing in the Windy City.
Why Tampa Won Out
Ultimately, Brady chose Tampa Bay, and the rest is history. The Buccaneers had a lot to offer in their own right: a warm-weather climate, an emerging offense with weapons like Mike Evans, Chris Godwin, and eventually Rob Gronkowski, who followed Brady to Tampa after coming out of retirement. Moreover, the Buccaneers’ aggressive front office promised to build a contender around Brady, including their all-in approach to free agency and trades.
Another significant factor was head coach Bruce Arians’ offensive philosophy. Arians’ “no risk it, no biscuit” mentality was perfectly tailored to Brady’s desire to continue pushing the limits, even in his 40s. Tampa’s offensive flexibility, combined with Brady’s hunger to prove he could win outside of New England, created a perfect storm that ultimately led him to Florida.
Brady has reflected positively on his decision to choose Tampa, citing the strong relationships he built with coach Bruce Arians and general manager Jason Licht as key factors in his success there. Tampa Bay’s roster, filled with talent and eager to win, was another major draw.
What Could Have Been for Chicago
For the Chicago Bears, Brady’s decision to choose the Buccaneers leaves fans wondering what could have been. Could Tom Brady have lifted the Bears out of their quarterback struggles and led them to the Super Bowl? Would Brady’s influence have unlocked the potential of their offense and maximized the talent on the roster?
It’s impossible to know for sure, but imagining Tom Brady in a Bears uniform will always be one of those great “what if” moments in NFL history. Chicago continues its search for a franchise quarterback, while Brady added yet another chapter to his legacy by bringing the Lombardi Trophy to Tampa Bay in his very first season.
As Bears fans ponder the missed opportunity, they can only dream of the possibility that one of football’s greatest ever nearly chose Chicago. While Brady may have passed on the Bears, the story of how close he came to choosing the Windy City will continue to fuel speculation and what-ifs for years to come.