In NFL history, few free agency decisions have reshaped the league like Tom Brady’s in 2020. But what’s less often remembered — and arguably just as fascinating — is the team that almost got him: the Los Angeles Chargers. Most fans know the story: Brady leaves the Patriots, signs with the Tampa Bay Buccaneers, and wins a Super Bowl in his first season there.
As Ari Meirov recently explained on the NFL Spotlight show, the Chargers were one of only two teams that made a serious push for Brady during that 2020 offseason. The Raiders showed early interest but backed out, leaving Tampa Bay and Los Angeles as the true finalists. While the Bucs went all-in — with Bruce Arians, GM Jason Licht, and others pulling every lever — the Chargers were right there until the end. Ultimately, Tampa landed Brady and set off a cascade of events that would ripple across two franchises.
Los Angeles Chargers-Tom Brady Sliding Doors: What Could Have Been
If Brady had chosen the Chargers, the impact would’ve been seismic. At the time, Los Angeles owned the No. 6 pick in the NFL Draft. With Brady in the fold, they almost certainly would not have used that selection on Justin Herbert, who has since become the franchise’s centerpiece. In fact, that pick may have been used to bolster an already solid roster, or possibly even traded for veteran reinforcements to help Brady win now.
Consider the Chargers’ roster at the time: Keenan Allen, Mike Williams, Austin Ekeler, Melvin Gordon, Joey Bosa, Derwin James — a group of ascending stars and Pro Bowl-caliber talent. With Brady at quarterback, that roster becomes a real contender in the AFC West. And given Brady’s gravitational pull, it’s not a stretch to imagine Rob Gronkowski joining him in L.A., just as he did in Tampa.
But the implications extend beyond Los Angeles. If Brady lands in L.A., the Buccaneers are left scrambling. Do they bring back Jameis Winston after a 30-interception season? Do they turn to Philip Rivers, who ended up in Indianapolis? And how different does Tampa Bay’s narrative look today without that Super Bowl title?
The Chargers, meanwhile, would have traded a decade-plus of potential with Justin Herbert for three (or more) seasons of Brady. Would it have led to a Super Bowl parade in Inglewood? It’s impossible to say. The AFC West gauntlet — with Patrick Mahomes and the Chiefs — would’ve made any playoff run grueling. But Brady has made a career out of silencing doubts.
As Meirov posed to fans: would you rather have had three years of Tom Brady and a guaranteed Super Bowl, or 15–18 years of Justin Herbert with an uncertain ceiling? The fanbase remains divided. Some say you never turn down a Super Bowl. Others are happy to bet on Herbert’s long-term greatness.
But either way, it remains one of the NFL’s great “what-if” moments — a fork in the road that could have defined two franchises in completely different ways.