Tom Brady, Chicago Bear? Apparently it almost happened in 2020, says Brady

Turns out Tom Brady isn’t done breaking teams’ hearts yet.

Chicago Bears fans, take a deep breath. Yes, drafting Mitchell Trubisky over Patrick Mahomes is Da Bears’ most painful “what if” of the 21st century. But this one might be a close second.

Think back to 2020. No, don’t remember the pandemic or the election. Remember how Brady and the Patriots parted ways? Remember how Brady entered the free agent market and immediately set the other 31 teams in the NFL on fire? He, of course, ended up with the Tampa Bay Buccaneers and brought the franchise its second ring. But as he noted on Sunday’s Fox broadcast from Tampa, he almost went north.

“There were a lot of reasons to choose Tampa, and I came up with about 18 criteria as to why, and it was all kinds of things ranging from salary obviously to the weather, the facilities and how great the players were,” Brady said. “At the end of the day, Chicago was a team, and I’ve never told that story before. They were very discreet in their recruitment. I seriously considered them.”

Brady held up the cards he used to make his decision, cards that are sure to break the hearts of Bears fans. “But ultimately it came down to Tampa,” he continued, citing the proximity of his son and then-head coach Bruce Arians, along with players like Mike Evans and Chris Godwin.

The revelation that he almost ended up in Chicago was Brady’s second big moment on the Buccaneers-Eagles broadcast, the first being his quiet war of words with Baker Mayfield. After hearing Mayfield’s comments that the Bucs wanted a less stressful environment post-Brady, the seven-time Super Bowl-winning ex-quarterback responded early in the broadcast.

That could have been you, Chicago.

With all due respect to Brady’s developing play-announcing skills, this is exactly what NFL fans expect from him: honest perspective and behind-the-scenes stories. However many of these he left in the tank, get them out, because that’s a lot more interesting than, say, routine analysis of the Eagles’ secondary.

During their three years with Brady under center, the Buccaneers won the NFC South three years in a row and captured a Super Bowl. During those same three years, the Bears finished second, third and fourth respectively in the NFC North, and reached the playoffs once, losing in their only game. Their quarterbacks along that stretch: Trubisky and Justin Fields. There’s no guarantee Chicago would have been better with Brady in uniform, but…ah, who are we kidding? Bears fans, you missed three years of glory. Sorry about that.