It's a pastime that often ends with the Patriots polishing another Vince Lombardi Trophy, Brady adding another Super Bowl ring to his collection and the doomsayers beating a hasty retreat.
Yet as the Patriots prepare to host the Kansas City Chiefs on Sunday, the guessing game surrounding Brady is back on.
"Are these Tom Brady's final days with the Patriots?" asked one headline this week, wondering whether the 42-year-old quarterback was preparing for life in retirement or even with another NFL franchise.
Although the Patriots are sitting comfortably on top of the AFC East at 10-2, and should easily reach the playoffs, this time the questions appear to be backed by the numbers.
With an under-strength receiving corps, the Brady-led offense is ranked 14th in the league.
Brady's frustration was evident in a sideline dressing down of his team-mates last Sunday as the Patriots lost 28-22 in Houston.
Brady though insists New England are in no mood to hit the panic button. "We're not 2-10, we're 10-2," he remarked this week.
"We're working hard and trying to do the right thing, and sometimes it's been good," Brady said. "Other times, we obviously still have work we still have to do. That is just part of playing football."
Patriots coach Bill Belichick also brushed off underwhelming statistics from recent outings.
"Our goal here is to win, not put up numbers," Belichick said. "The number we're concerned about is the wins and losses. That's the way it will always be as long as I'm here and we'll focus on that."
- Going nowhere soon -
Belichick's opposite number on Sunday, Chiefs head coach Andy Reid, is also sceptical that Brady is on the wane.
"He doesn't seem to age," Reid said. "He's a great football player. That's what I see."
Chiefs quarterback Patrick Mahomes also doesn't see Brady going anywhere.
"It's not gonna be his last year any time soon," Mahomes said. "He's still playing at a high level. Unless he just doesn't want to play, which I don't see, I expect to see him for at least a couple more years."
Elsewhere this weekend, the San Francisco 49ers face another test of their championship credentials when they take on fellow Super Bowl contenders New Orleans in the Superdome.
The impressive 49ers are looking to bounce back after a loss to Baltimore last week, and Saints quarterback Drew Brees is bracing for a physical afternoon against one of the best defenses in the league.
"They've been pretty dominant," Brees said of the 49ers defense. "They have really good players across the board and there's no weak links. Big, strong physical, very well coached. Just very sound in everything that they do. The statistics reflect it, the numbers reflect it, the wins reflect it."
A win for the Saints on Sunday would leave them firmly on course for homefield advantage throughout the NFC playoffs.
Their nearest challengers for that No.1 seeding are the Seattle Seahawks, who improved to 10-2 on Monday with their 37-30 win over the Minnesota Vikings.
The Seahawks travel to the Los Angeles Rams on Sunday looking to tighten their grip on the division.
Wilson believes the Seahawks, who have already beaten San Francisco this year, are quietly building towards the sort of form that landed the franchise the Super Bowl in 2014.
"There's nothing that this team can't do, and I think it's about each other and it's about how we're going to go accomplish it together," Wilson said this week. "We're excited about the opportunity."