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We've been blessed with all time greats, perhaps greatest ever, at both the Head Coach and Quarterback position for the last 15 years. The Patriots have won four Super Bowls, been to six, and played in 10 conference championships. The Patriots are the first and so far only dynasty of the 21st century in the NFL, but the reality is everything does not last. The Patriots are in a similar arena to where the 49ers stood in 1997 and the Steelers in 1984. In the case of those two examples, the franchises wound up struggling after their respective dynasties ended. The Patriots window with Tom Brady and Bill Belichick can't be expected to last longer than the expiration of Brady's contract after the 2017 season.
2016
The 2016 season will be the end of the Patriots current window as Super Bowl contenders. The majority of the core of the team will be eligible for free agency and the Patriots will inevitably not be able to keep all of them with a hard salary cap in place. That means the Patriots will have to prepare a possible contingency plan for losing Chandler Jones, Dont'a Hightower, Jamie Collins, Jabaal Sheard, and Malcolm Butler on defense. Outside of Hightower and Collins, the Patriots do have options to work with for the future past 2016. The Patriots need to extend at least three of those players to set up the 2017 and beyond contention window.
On offense, the Patriots have aging WRs and were decimated by injuries on the OL. The Patriots don't have a player who could start for them in 2017 with Marcus Cannon and Sebastian Vollmer set to become free agents and neither player worth keeping around for very long. The Patriots likely will have to draft their starting RT in 2017 in the 2016 draft because signing free agents are expensive. At the WR position, the Patriots must be able to shake off past demons and develop a successful strategy for identifying potential WR prospects. Perhaps a shift to Pro-Style offenses may be the trick considering the Patriots most successful college WR prospects came from Pro Style. For anyone that brings up Julian Edelman, he wasn't a college WR.
The 2016 offseason will set up the post-Brady core in both the draft and which players the team extends. The Patriots need to take care of their stars and keep them around long term. The Patriots have built up their defense to be a top unit over the last four years, now it's time to improve the talent pool on the offense. Belichick prides himself in having a top defense, so it wouldn't surprise me if he drafts a LB or DB ahead of an OT or WR, it really comes down to who's on the board and what options he has to move up/down or stay put. The Patriots do have some solid talent on the offense, but without Tom Brady the unit as a whole drops a couple tiers. The team will have to take on a similar identity from 2001-2006 where the defense and running game carrying the offense.
Free agents I expect to not return in 2017 are Rob Ninkovich, Sebastian Vollmer, and Alan Branch because of age. Danny Amendola and Marcus Cannon are restructure candidates that I also see getting the door after the 2016 season because there are cheaper replacements available in this year's free agent pool. The Patriots have already drafted Branch's and Nink's replacements in the 2015 Draft. The Patriots will have to draft Vollmer's replacement in the 2016 Draft as I stated above.
2017
The most important decision for the franchise will be the quarterback. Tom Brady and Jimmy Garoppolo's deals simultaneously expire after the 2017 season. The Patriots can keep Tom Brady another year with the franchise tag, but all that does is punt the decision to the next season and that's never a good idea. The Patriots need to make a decision on who their QB of the future is. Is it Brady, Jimmy G, or someone else? In 2017, I would not be surprised if the Patriots did draft a QB in the first round if one became available because that 5th year option is ridiculously valuable to franchises. If the Patriots choose their QB and it's Brady or Jimmy G then they should try to get an extension done in the 2016 offseason if possible. I would not be surprised for Brady to move cap space into future years via restructure to force the Patriots hand with the window possibly closing in 2016.
If the Patriots do make a change at the QB position, then the offense needs to change as well to fit the strengths of the new QB. If it's Garoppolo, the offense will change to include more plays that take advantage of Garoppolo's mobility skills in and out of the pocket. Garoppolo doesn't have the field experience that Brady has, so the reads need to be more simplified for him as he starts gaining that experience. An offense led by Garoppolo will likely need a stronger run game because Brady is the only QB who can win a game throwing 50+ times and even that is a dangerous strategy.
The Patriots biggest FA for 2017 outside of the QBs includes James White, Bryan Stork, Patrick Chung, and Malcolm Butler. Of these three, the Patriots most important player to extend is Butler then Stork. White is very fungible as a receiver-only type RB compared to the other two not mentioned. Chung's position can be replaced by a safety with similar skills such as Jordan Richards, although in 2017 they should prepare to draft Chung's replacement anyway in case Richards on-field play doesn't match his football IQ.
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I believe Belichick will still be the head coach after the 2017 season, but there will come a point where he will inevitably walk away from the game. We won't know when and what the team does after that. Bill Belichick will quickly deflect questions beyond what's important for that day and week. As for the roster, the Patriots will have to quickly find the next window of contention and whether it will include Tom Brady or not. The Patriots have stars to extend and decisions to make about who will lead the franchise in the future from the headsets and from under center. It's going to be hard for the next guy to follow behind those two.