Bears chairman George McCaskey confirms pursuit of Tom Brady in 2020 free agency

WARE, England - While standing with an England park backdrop against his back, Bears chairman George McCaskey was asked to recount history.

Specifically, the five quarterbacks' worth of history dates back to 2020 when McCaskey confirmed the Bears were interested in former NFL MVP Tom Brady during his free agency in 2020.

"That seems like ancient history at this point," McCaskey said. "I do remember we were interested."

McCaskey couldn't confirm if Brady made it to Halas Hall for a visit, but the interest was mutual in the end.

During his broadcast of the Bucs' game against the Philadelphia Eagles on Sept. 29 afternoon, FOX Sports' lead NFL analyst said that the Bears were a "stealth" contender to sign him when he left the New England Patriots as a free agent in the 2020 offseason. Brady said he "seriously" thought of playing the remainder of his career in Chicago.

"Ultimately, Chicago was a team — and I never told that story before — they were very stealth in their recruitment," Brady said. "I was seriously considering them."

Brady decided on signing with Tampa Bay.

That year, Brady's first season in Tampa, the Bucs won the Super Bowl LVI. The team also made the playoffs in his three seasons, and he retired after the 2022 NFL season.

In his three seasons in Tampa Bay, Brady completed 66.7 percent of his passes, threw for 14,643 yards and tossed 108 touchdowns. 

"In the end, it came down to Tampa. It was close to my son Jack. I love Bruce Arians and the role he played in the offense. And ultimately, the great players like Mike Evans and Chris Godwin that I'm still out there watching today."

The Bears went 8-8 in 2020 and made the playoffs with then-quarterback Mitchell Trubisky in 2020. The Bears lost to the New Orleans Saints in the NFC wild-card round. The Saints lost to Brady's eventual Super Bowl champion Bucs in the divisional round the week after.

Following the 2020 season, the Bears moved on from Trubisky and drafted Justin Fields in the 2021 NFL Draft. The Bears fired head coach Matt Nagy and general manager Ryan Pace following that 2021 season.

"It didn't work out for us," McCaskey said. "Worked out great for him in Tampa."