Kyle Shanahan expresses mild regret over 2020 Tom Brady decision

Kyle Shanahan regretted not signing Tom Brady to the 49ers when he was a free agent in 2020.

When Tom Brady hit free agency in 2020 after spending 20 seasons with the New England Patriots, there was a question of where he would go. Brady was fresh from a Super Bowl win in the 2018 season; however, his final year in New England left many wondering if the seemingly never-happening decline had begun.

Just a season after winning their sixth Super Bowl Championship, the Patriots appeared to be suffering from a Super Bowl hangover as they had a less-than-stellar 2019. They ended the 2019 season with a loss in the wild-card round to the Tennessee Titans.

In 2019, Brady signed a 2-year contract extension with the Patriots, worth $70 million through to the 2021 season; however, the contract terms allowed Brady to become a free agent in 2019. The day before his contract expired, Brady announced that he would not re-sign with the team for the 2020 season, ending his 20-year tenure in New England.

Brady then signed with the Tampa Bay Buccaneers.

The Buccaneers proved they had made the right decision by signing Brady, as in his first year on the team, he led them to their second-ever Super Bowl and his seventh.

49ers: Kyle Shanahan may regret not signing Tom Brady in 2020

As the San Francisco 49ers and Tampa Bay Buccaneers are set to face off in Week 14, 49ers head coach Kyle Shanahan was asked if he was surprised that Brady did not decline after the 2019 season. Shanahan stated, per NBC Sports:

"“I’d like to say of course not, but I think everyone since then, you’re wondering when is the number too high? but now like when you watch him that first week in Tampa, you’re like, what the hell was anyone thinking? The dude looks the exact same, he did that year [in 2020]. He does when he comes off injuries and I think he’s playing as good now and throwing the ball as well now as I’ve seen anybody do it.”"

Shanahan expressed more praise for Brady:

"He plays the postion better than anyone ever and he’s definitely the GOAT from what I’ve seen, but I don’t say that just because he has won Super Bowls, I say it because of how he plays the position. The ball always goes to the right spot and that answer is based off of a thousand different things that could be matchups, it could be the coverage that could be based off of down and distance, the time in the game, how the defense is playing.”"

A year before Brady hit free agency in 2020, the 49ers had a stellar 2019 season. Led by quarterback Jimmy Garoppolo, a former Patriots teammate of Brady’s, they had a 13-3 record and would advance to the Super Bowl, where they lost to the Kansas City Chiefs. Despite the Super Bowl loss, the 49ers had Garoppolo, who had proven he could win and play at a high level. Did they need Brady when they already had a younger, successful quarterback in Garoppolo? After what he did in 2020, maybe they regret not signing Brady after all.

Tom Brady anticipates the 49ers matchup

Brady, a San Mateo, California native, grew up as a 49ers fan. He idolized the 49ers’ legendary quarterback Joe Montana. He was in attendance, at Candlestick Park, for the iconic “The Catch” play, where Montana threw a 6-yard touchdown pass to receiver Dwight Clark in the back of the end zone, which is highly regarded as one of the greatest plays in NFL history.

In a recent press conference, Brady expressed how much he loved the 49ers growing up and also how he came to hate them. He said, per NBC Sports Bay Area:

"“I always consider myself a California kid and grew up loving Joe Montana and Steve Young. Going to 49er games is where I fell in love with football and we’d sit up there in the nose bleeds…I was lucky to grow up in the Bay Area.“I love the 49ers. I loved them through college and they skipped over me six times and I started to hate the 49ers.”"

As he is set to be a free agent once again in 2023, there is a chance Brady finally becomes a 49er if he chooses not to retire or re-sign with Tampa Bay.

Tom Brady has faced the 49ers three times in his career, all with the Patriots. He has yet to meet his childhood team as a Buccaneer, and he is currently 2-1 against San Francisco.