When Tom Brady left the New England Patriots in 2020, several NFL teams were eager to sign the legendary quarterback. The Miami Dolphins even lost a draft pick due to tampering violations in their attempt to lure Brady while he was still under contract.

Now, another team has come forward, confirming they were in the running for the seven-time Super Bowl champion: the Chicago Bears.

In a recent conversation with reporters, Bears chairman George McCaskey revealed that the team had indeed explored the possibility of signing Brady during his free agency period.

However, McCaskey was quick to acknowledge that the pursuit never gained serious traction. “I do remember we were interested in pursuing him,” McCaskey told ESPN. “It didn’t work out for us. Worked out great for him in Tampa.”

McCaskey explained that while the Bears saw Brady as an option, they weren’t fully committed to him as their top priority. “Anytime you’re in a situation like that, you’re not putting all of your eggs in one basket. You’re looking at alternatives,” McCaskey said. “It’s the same in free agency, it’s the same in the draft. If the person you’re targeting isn’t available, you want to make sure that you’ve done your due diligence on all other options. So that was one option that we were looking at.”

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Looking back, it’s easy to wonder if the Bears should have been more aggressive in their pursuit of Brady. In 2020, Chicago made the playoffs with Mitchell Trubisky as their starting quarterback but bowed out early. Since then, the Bears have endured three consecutive losing seasons, struggling to find a long-term answer at the quarterback position.

Meanwhile, Brady’s move to the Tampa Bay Buccaneers instantly transformed the team. The Bucs, already boasting a talented roster, added the future Hall of Famer and immediately reaped the rewards. Brady led Tampa Bay to a Super Bowl victory in his first season and kept the team competitive until his retirement in 2023. McCaskey acknowledged the success of Brady’s decision, saying, “It certainly worked out great for him in Tampa.”

However, McCaskey also suggested that even if Brady had chosen Chicago, it’s unlikely the Bears would have achieved the same level of success. Unlike the Buccaneers, who had a strong supporting cast and a solid infrastructure already in place, the Bears were a team in transition.

Their offensive line and receiving corps were not as strong as Tampa’s, and the defense, while capable, wasn’t at the level needed to carry the team deep into the playoffs. “We weren’t all-in on Brady,” McCaskey admitted. “We were looking at him as one of several options.”

Had the Bears signed Brady, they likely would have improved their win total and made the playoffs. But whether Brady could have turned Chicago into a Super Bowl contender remains uncertain. The Bears’ roster at the time was not as stacked as the one in Tampa Bay, which boasted stars like Mike Evans, Chris Godwin, and a dominant defense. Even with Brady, the Bears might not have enjoyed the same level of success the Buccaneers did.

Additionally, there’s the question of how long Brady would have stayed in Chicago. He signed a two-year deal with Tampa Bay but ended up playing three seasons with the Bucs.

Given the Bears’ instability at the time, Brady might have been more inclined to leave after a short stint, especially if immediate success wasn’t guaranteed.

In the end, while it’s easy to speculate about what might have been, the Bears’ pursuit of Brady was just one of many options they considered in 2020. The quarterback ultimately chose Tampa Bay, where he added yet another chapter to his illustrious career. As McCaskey noted, “It didn’t work out for us, but it worked out great for him.”

Would signing Brady have altered the course of the Bears’ recent struggles? Perhaps.

But given the differences in the infrastructure and roster strength between the Bears and the Buccaneers, Chicago likely wouldn’t have experienced the same overnight success.

Still, with their ongoing quarterback woes, Bears fans can’t help but wonder: should they have gone after Brady harder?