Bears Owner George McCaskey Expands on Failed Pursuit of Tom Brady in 2020

In 2020, the Chicago Bears were at a crossroads. After a superb 2018, they had slogged through an 8-8 season in 2019—and were already pondering a future without quarterback Mitchell Trubisky.

As they weighed their options, they reached out to New England Patriots quarterback Tom Brady—then a free agent. That's per the man himself, who told the story while calling the Tampa Bay Buccaneers' 33–16 win over the Philadelphia Eagles on Sept. 29.

On Thursday morning in England, Chicago chairman George McCaskey confirmed that and discussed the team's past interest in Brady.

"I do remember we were interested in pursuing him. It didn't work out for us. Worked out great for him in Tampa," McCaskey told reporters via Courtney Cronin of ESPN.

Brady led the Buccaneers to a victory over the Kansas City Chiefs in Super Bowl LV that very season.

"Anytime you're in a situation like that you're not putting all of your eggs in one basket. You're looking at alternatives. It's the same in free agency, it's the same in the draft," McCaskey said. "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."

By leaps and bounds, Brady would have been the most talented quarterback ever to play for the Bears. Chicago's single-season passing yards record is held by quarterback Erik Kramer in 1995 with 3,838; for comparison's sake, Brady eclipsed that total in 15 different seasons.