Was the 49ers' free agency error in 2020 one of the biggest in NFL history?

When Tom Brady entered free agency in 2020, his number one landing spot was with the San Francisco 49ers.

An excerpt from Seth Wickersham's new book, "It’s Better to Be Feared: The New England Patriots Dynasty and the Pursuit of Greatness," published by Sports Illustrated, revealed how San Francisco was top of Brady's list when he was searching for a location for the "final chapter" of his historic and illustrious career.

Brady, then 42 years old, reached out to his former New England Patriots teammate and 49ers wide receiver coach, Wes Welker, to sound out the possibility of making the move back to his home state of California.

Brady was ready to pack his bags, head straight to the Bay, and pull on the jersey of his boyhood team, the 49ers. But in a sliding door moment, general manager John Lynch and head coach Kyle Shahanan passed on the opportunity to bring the then six-time Super Bowl-winning quarterback on board.

What caused them to make that decision? And, given what Brady has gone on to achieve with the Tampa Bay Buccaneers, was it one of the biggest errors in NFL history?

Why did the San Francisco 49ers not sign Tom Brady in 2020 free agency?

The 49ers were still licking their wounds from their Super Bowl LIV heartbreak, a 31-20 loss to the Kansas City Chiefs when Lynch and Shanahan learned about Brady's interest in moving to Golden Gate City.

Brady's former teammate, Jimmy Garoppolo, was potentially a couple of plays away from winning a Lombardi Trophy in his first year as an NFL starter. After going 13-3 that season, the 49ers' brass were feeling good about Garoppolo.

The excerpt from Wickersham's book explains:

"Brady rarely failed in those moments. He knew it, and he knew that the 49ers’ coaches knew it. The 49ers were tepid, but realized they had to listen. One of the greatest football players of all time, capable of elevating an entire building with his preparation and mentality alone, was offering his services. Kyle Shanahan instructed the offensive coaches to watch all of Brady’s 2019 throws. He did so himself, turning his Cabo vacation into a film session."

It seems that Shanahan was willing to acknowledge the limitations in Garoppolo's play, not to mention the fact that the QB was not able to execute under the brightest spotlight – with the game on the line in the Super Bowl. But Garoppolo still ended up being the 49ers' preference. Their decision is described below:

"The coaches liked Brady’s film—but didn’t love it. He was better than Garoppolo, they thought, but not that much better—not so much that it was worth trading away a locker-room leader, not to mention one who was nearly 15 years younger and coming off a Super Bowl appearance."

The rest is history. At the time, Lynch and Shanahan were likely not anticipating trading up to number three overall to select a quarterback in the 2021 NFL draft. With the benefit of hindsight, it's easy to say they made the wrong decision.

Was it the biggest mistake in NFL history? That's a big call. But the 49ers have not won a Super Bowl since Steve Young downed the San Diego Chargers in 1994. Place the 2020 and 2021 version of Brady into Shanahan's offense, and it's potentially the 49ers that are charging towards back-to-back Super Bowl wins.