Tom Brady Strongly Considered Bears During 2020 Free Agency

A free agent ahead of his age-43 season, Tom Brady‘s decision produced numerous headlines four years ago. Nearly a third of the NFL was connected to the all-time QB great, with the passer-turned-broadcaster’s final decision believed to be a Buccaneers-or-Chargers call.

That may well have been the case, but Brady — doing his fourth regular-season broadcast for FOX (h/t FOX Sports’ Ralph Vacchiano) — confirmed the Bears were part of his decision-making process. We heard in September 2020 the Bears made an offer to the then-20th-year quarterback but lost out due to multiple factors, but Brady said Sunday he gave “serious consideration” to choosing Chicago.

When the Bears-Brady connection surfaced four Septembers ago, the NFC North team was described as “in the running.” A cold-weather city did not appeal to Brady at that point, and the quarterback was intrigued by throwing to Mike Evans and Chris Godwin while playing closer to his oldest son, Jack, whose mother is actress Bridget Moynahan. Brady also mentioned Bruce Arians playing a key role in convincing him to sign with Tampa Bay, which gave him a fully guaranteed $50MM deal over two years.

The Bucs and Chargers were both agreeable to Brady’s terms by the end of the process, pointing to the Bears potentially finishing third here. The ageless passer had been interested in his hometown 49ers, who stuck with Jimmy Garoppolo, and replacing Drew Brees — had he chosen to retire, which the future Hall of Famer did not — as well. Among realistic options, Chicago joined L.A. in needing to take another route after the high-profile FA’s decision.

At that point, Chicago was coming off an 8-8 season — a step back from its 12-4 2018 showing — and had begun to determine Mitch Trubisky was not going to be the franchise option they’d envisioned. The Bucs and Chargers did not have starting QBs under contract, with Jameis Winston and Philip Rivers each free agents. This Bears’ pursuit also differed from the Raiders’ effort, as Las Vegas then bowed out early — as Brady has famously discussed — and had a second-contract QB (Derek Carr) rather than a former first-round pick playing on a rookie deal.

That Bears edition rostered Allen Robinson, who was heading into his third season with the team; Darnell Mooney arrived weeks later as a fifth-round pick. Chicago had Matt Nagy calling plays with an offensive line that included the likes of Cody Whitehair, James Daniels and veteran tackles Charles Leno and Bobby Massie. Pieces from Vic Fangio’s defenses still comprised much of Chicago’s depth chart on that side, with Khalil Mack, Roquan Smith and Akiem Hicks anchoring the unit. The Bucs, however, checked more boxes and were quite willing to accommodate their free agency prize in free agency and trades.

Brady undoubtedly would have elevated the Bears’ setup, with Rob Gronkowski — and, for better or worse, Antonio Brown — presumably following wherever his Patriots QB went. But it is safe to say his Bucs decision was correct, seeing as he piloted Tampa Bay to its second Super Bowl title that season and earned second-team All-Pro honors at age 44 in a statistically superior campaign a year later.

The Bears are now multiple starting QBs removed from that what-if, having drafted both Justin Fields and Caleb Williams after letting Trubisky walk in 2021. After Brady’s decision, Chicago traded for Nick Foles as a player to push Trubisky. Although the latter opened the season as the team’s starter and reclaimed his job from Foles down the stretch — en route to an 8-8 season that did produce a playoff berth — the former No. 2 overall pick has been unable to prove worthy of a starting job since.