With the window closing, if Belichick/Brady don't win another championship together, how would their legacies be affected?
Stephen: If Brady and Belichick aren't able to win another title, I think their legacies lose some luster. These two are considered the best at their positions in this era, and I think they would firmly cement themselves as the best duo ever by capturing at least another title or two. Also, they haven't won since 2005, so it would help for them to go out on top.
Jason: I think it's safe to say that the legacies of Brady and Belichick are already etched in stone. The list of quarterbacks with three or more Super Bowl wins is pretty short (Joe Montana, Terry Bradshaw, Troy Aikman, all Hall of Famers). The group of head coaches with at least three Super Bowl rings is equally exclusive (Chuck Knoll, Joe Gibbs and Bill Walsh, all Hall of Famers). B&B are already in the discussion for the best coach/QB combo in history. Based on what they have already accomplished, I don't think it's absurd to say that another ring or two wouldn't change a whole hell of a lot in terms of their legacy.
Rick: The legacies of Tom Brady and Bill Belichick are set in stone right now and they will go down as one of the best QB-coach combos in the history of the sport. Despite not winning a title since 2005, you have to look back at the coaching jobs Belichick has had. You can look at 2008 where the Pats went 11-5 with a QB in Matt Cassel who hadn't take a snap since high school. Also, look no further than last year when New England went 14-2 with one of the youngest defenses in the league. Even though Brady is not putting up the rings, he is putting up some awesome numbers with a makeshift receiving core to add to that resume. They will win 1 or 2 more, but either way, they are still a top duo.
Derek: For Brady and Belichick, another title is the difference between being rememberd as one of the best and being remembered as THE best. As it stands, they will go down in history with the 60's Packers, the 70's Steelers, the 80's Niners, and the 90's Cowboys, and a fair case can be made that they dominated their decade of the 00's more than any of those four dynasties that I just mentioned. If you add a fourth title to the mix, they managed to separate themselves even further from the pack, and if they can somehow grab a fifth, they will stand alone in the history books.