Could Tom Brady have joined the Chicago Bears during free agency?

If it wasn’t already clear, Tom Brady is going to take us on a wild ride this NFL season and we’re going to love it every step of the way. On Sunday, not only did Brady take a moment to fuel a potential feud by cooking Baker Mayfield, after the Bucs’ current QB suggested Brady’s tenure was a “stressed out” period for the team, but he also alluded to a team that he could have potentially joined four years ago.

Tom Brady & the Bears talked about it in 2020

There was a sense of confusing nostalgia on Sunday as Tom Brady took the field at Raymond James Stadium in Tampa Bay, Florida. Indeed, it was a scene we watched in awe during the 2020-21 NFL season as Brady marched the Tampa Bay Buccaneers to a Super Bowl title. Yet, this time, Brady was there in his new capacity as an analyst for FOX Sports. Of course, one could be forgiven for forgetting that as he interacted with players on the field, even taking a moment to chat with Bucs quarterback, Baker Mayfield. You can read about why that’s significant here.

Nonetheless, it wasn’t long before Brady got to work and during the broadcast proceeded to reveal a rather interesting anecdote from his career which we didn’t know before. As the Bucs took on the Philadelphia Eagles in a Week 4 clash, Brady disclosed that he almost joined the Chicago Bears in 2020. As we know, the NFL great eventually joined the Buccaneers and the rest is History, or rather historic. So why didn’t he go to Chicago? That’s where things got interesting, as he then explained that he created 18 criteria for each of the franchises he was considering after leaving the New England Patriots.

The Patriots legend didn’t stop there either. He even showed the notecards that he used at that time to help him with his decision. Going further, Brady explained, “Chicago was a team, and I’ve never told that story before, they were very stealth in their recruitment. I was seriously considering them, but in the end, it came down to Tampa. And it was close to my son Jack, I loved Bruce Arians and the role that he played in offense, and ultimately the great players like Mike Evans and Chris Godwin that I’m still out there watching today.”

Now, there is really no way to fathom what the landscape of the league would have looked like had Brady made his way to the Windy City. As we know, he would go on to lead the Buccaneers to a Super Bowl title during his first season in Tampa and in so doing make NFL history by claiming a seventh ring. The three-time league MVP also picked up a fifth Super Bowl MVP in the process.

Ultimately, what followed was two more seasons in Florida and then retirement. The Bears, on the other hand, started that season 5-1, before losing six straight while depending on a combination of Mitch Trubisky and Nick Foles under center which is to say, the addition of Brady couldn’t have hurt at all.