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BigPaulSports > Blog > Game Analysis > Tom Brady: Bears Were ‘Pretty Much All-in’ Recruiting Me Back in 2020
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Tom Brady: Bears Were ‘Pretty Much All-in’ Recruiting Me Back in 2020

BigP
Last updated: 2025/09/18 at 3:09 PM
BigP Published September 18, 2025
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Tom Brady: Bears Were 'Pretty Much All-in' Recruiting Me Back in 2020
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Contents
Tom Brady Story Time: How the Bears nearly landed the GOAT 🤯 Inside the Infamous 4th Down IncidentTom Brady’s Week 2 Power Rankings 🚨

Tom Brady returns to Chicago this weekend for “America’s Game of the Week,” which will take place at a stadium he once thought about calling home.

In his first season as FOX Sports’ lead NFL analyst, Brady shared that the Chicago Bears were a “stealth” contender to land him when he became a free agent for the first time in 2020. Now, the GOAT is sharing that he was closer to landing in the Windy City than many of us realized. 

“They were pretty involved,” Brady said of the Bears’ pursuit in free agency. “A lot of things happened in free agency and different kinds of teams come out of the woodwork. I really wasn’t expecting Chicago to be one of them, but they were pretty much all-in. It was a strong consideration for a long time.”

Tom Brady Story Time: How the Bears nearly landed the GOAT 🤯 Inside the Infamous 4th Down Incident

Tom Brady Story Time: How the Bears nearly landed the GOAT 🤯 Inside the Infamous 4th Down Incident

Chicago’s pursuit of Brady came after Mitchell Trubisky’s underwhelming 2019 season, taking a step back after helping Matt Nagy and the Bears win 12 games in 2018. As a result, the Bears went 8-8 and missed the postseason as they weren’t viewed as a true Super Bowl contender. 

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But that didn’t stop Brady from preparing himself to take on the challenge of becoming the quarterback of the Bears, which might be one of the most cursed positions in all of sports. 

“I liked the idea of being there,” Brady said of Chicago. “There were a lot of things that were to like about being there.”

One of the reasons he might have liked joining the Bears was the defense the team had at the time. Khalil Mack was still one of the top edge rushers in the league and Chicago had been one of the top defensive units across the NFL in the two seasons prior to Brady’s free agency. 

Soldier Field might have also been on the list of things to like about playing in Chicago. 

“It’s one of those NFL stadiums that has aura,” Brady said. “You go there and you look around and you think of all the great Bears players that have played for that organization — I have played there several times, and it’s like a pinch-yourself moment to go out there and play well in this environment.”

But while Brady wasn’t afraid of playing in the cold weather, the proponent of playing for a team in a warmer climate was enticing after spending 20 seasons with the New England Patriots. So, Brady wound up signing with the Tampa Bay Buccaneers instead. 

“Being down here in sunny Florida is pretty great. It’s a pretty good quality of life,” Brady said. “Those extra three years in the warm weather kind of helped my, a little aging body get through the football process a little bit easier.”

Tom Brady’s Week 2 Power Rankings 🚨

Tom Brady’s Week 2 Power Rankings 🚨

Tom Brady lists his top 10 teams for Week 2 which include the Detroit Lions, Washington Commanders, Los Angeles Rams and more!

Brady’s decision to sign with the Buccaneers immediately paid dividends. He led the Buccaneers to a title in his first season with the team, capturing his seventh Super Bowl victory.

Of course, Brady got some help from his Tampa teammates. Mike Evans and Chris Godwin were arguably the top wide receiver duo in the NFL at the time, which could’ve intrigued Brady to sign with the Buccaneers over the Bears. But Chicago also had a talented receiver at the time in Allen Robinson, who had 1,250 yards in 2020, to go with David Montgomery, who was emerging as one of the game’s top running backs at the time. 

But Brady continued to harp about the major climate difference between Chicago and Tampa Bay.

“I’ve been there long enough to know what the weather forecast is in early March, and it’s not pretty,” Brady said. “The summers in Chicago, I spent a lot of those coming down from Ann Arbor to visit a lot of friends from Chicago. But the winter times there, those probably weren’t my favorite.”

As Brady makes his way to Soldier Field to call Sunday’s game between the Cowboys and Bears, he could think about what could’ve been for him in Chicago. However, he’s still got the weather on his mind.

“You know what, I’m going to check the forecast right now,” Brady said. 

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BigP September 18, 2025
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