2020 is less than two weeks old, but the Patriots have already entered into uncharted territory when it comes to numerous different elements of their franchise.

They had to play in their first Wild Card game since 2009, and were bounced out of the playoffs before the AFC Championship game for the first time since the 2010 season.

Away from the field, they’re in just as unique of a situation. While every year seems to bring questions about a potential end to New England’s dynasty, 2020 may serve as the first real dose of reality when it comes to any of those predictions.

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The team’s wide receiving corps is in shambles, and the laundry list of expiring contracts and injuries across the roster continues to grow. Their coaches are in a state of flux, with special teams/wide receivers coach Joe Judge heading to MetLife Stadium to become the head coach of the Giants, and offensive coordinator Josh McDaniels interviewing for a head coaching job with the Browns.

But, the biggest question mark of them all? It corresponds with one name: Tom Brady.

For the first time in his career, Brady has all of the freedom in the world to decide on his destination for the next NFL season. He’s been generous throughout his tenure in the league as it relates to team-friendly contracts, shifting money around in his contract numerous times to create financial space for the team to sign other assets on both sides of the ball.

But, circumstances change, and 2020 serves as the chance for Brady to embrace the motto, “New year, new me.” Does he want to spend his remaining years in the league as a member of the Patriots, finishing out his career with the team that drafted him? Or, is it time to get the money he’s earned over the last 20 years with a different offense in a brand new city?

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The situation is a tricky one, despite how simple things seem to be. It sounds like Brady wants to be back in New England. It sounds like Bill Belichick wants Brady to come back to the team, and it sounds like Patriots owner Robert Kraft wants Brady to either re-sign with the team, or retire as a Patriot.

So, with all of that in mind, why is it so hard to make it all happen as soon as possible? Because there’s more than nostalgia to worry about.

The 2020 offseason will undoubtedly turn into a game of chess between all three parties. Brady moved the first piece on the board when asked about the upcoming offseason in an interview with Peter King.

“I’ll explore those opportunities whenever they are,” Brady said after his season ended in a Wild Card loss to the Titans. “If it’s the Patriots, great. If that doesn’t work, I don’t know. I just don’t know. I love playing football. I still want to play football. I think I still can play at a championship level. I’ve just got to go do it. I’m motivated to get back to work and training.”

While Belichick strayed away from answering any questions about the future, as it relates to both Brady specifically and the Patriots as a whole, in the immediate hours and days following the end of the Patriots season, Brady chose to break any silence relatively quickly.

He posted a lengthy message on Instagram on January 8, just four days after the Wild Card loss, to confirm that he wasn’t done playing in the NFL.

“In both life and football, failure is inevitable,” Brady wrote. “You don’t always win. You can, however, learn from that failure, pick yourself up with great enthusiasm, and place yourself in the arena again. And that’s right where you will find me. Because I know I still have more to prove.”

While digging deep into an Instagram post like this may seem meaningless, Brady seems to drop some hints throughout the text to imply that he’s leaning towards a return to Foxborough in the fall. He uses phrases like “an organization that believes in me,” and highlighting what “TEAM is all about.”

He also mentions the need to “place yourself in that arena again,” followed by saying “that’s right where you will find me.” If the tea leaves are correct, it sounds like Brady wants to be playing at Gillette Stadium at least eight more times next season.

However, there are other teams that Brady may look at and see appetizing options, such as the Chargers in their new stadium in his home state of California, or a talented team in need of a mentor for a young quarterback, like the Colts with Brady’s old teammate Jacoby Brissett.

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Brady has options to work with, and seems like the party with the most say in the matter when it comes to where he wants to land. But, just like in chess, there are other players who need to make moves, as well.

In this case, the next logical consideration comes from Belichick.

Does the eight-time Super Bowl champion believe that the 42-year-old Brady (who will be 43 when the 2020 season starts) can still get the job done in the offense he wants to run? Or is he okay letting the man who helped him win six Super Bowls walk, saving him money to develop his quarterback of the future?

Belichick has never been one for nostalgia when it comes to his business decisions, although he’s shown off his affinity for history during his time in studio for the NFL 100 All-Time Team show on the NFL Network.

But, the relationship between he and Brady has been a strong one over the last two decades, evident by their time together on the quarterbacks episode of the All-Time Team specials, and could be enough to sway the Patriots head coach for a few years.

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Then, in Kraft’s case, he’ll move any of those chess pieces around if it means he can keep Brady in New England for his entire career.

“I love the young man like he’s part of my family,” Kraft said during Wild Card weekend. “Blood family. Anyone who’s done that has earned the right to control his future after 20 years.”

“My hope and prayer is number one, he play for the Patriots, or number two, he retires,” Kraft continued. “He has the freedom to decide what he wants to do and what’s in his own best personal interest.”

While he’s giving Brady the ability to make his own choices, just like any parent, he undoubtedly has his own mindset for how he wants the next two months to play out. Releasing comments like Kraft did could make an impending free agent further recognize how loved he is by his current organization, and how much swing he may have in a return to that team.

While Brady is getting his pawns in order and Belichick is looking to protect his king, Kraft is moving his knights, bishops and rooks away from the spotlight to try and get what he’s looking for.

But, after all of these mind games, what’s next? It’s tough to say, considering the factors that have added up over the last six months:

Brady has turned into a real estate master, selling his Brookline, Massachusetts home in the midst of a reported search of new housing in Connecticut.

The Patriots offense fell apart in the second half of the season, with the organization taking away Brady’s offensive weapons by cutting Antonio Brown and Josh Gordon.

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Brady looked lackluster during the home stretch of the season, with key losses to the Dolphins at home and Titans in the playoffs amplifying the negatives

Any negotiations between Brady and the Patriots stalled out after August, when his initial “extension” was signed which would void the last two years of the Patriots quarterback’s deal when the end of the 2019 season came around.

In the end, it’s tough to see Brady leaving New England with all of the information in hand, especially given the talent the Patriots possess on defense to help bail out the offense in any poor performances.

He’d have the largest leash with the coach he’s played for over the span of 20 years, and he can sign a deal which could help the team surround him with receiving talent to help him out as a 43-year-old quarterback. And, if it comes down to a $25 million deal with the Colts or a $20 million deal with the Patriots, it’s hard to imagine Brady chooses to uproot everything for a new offense for an extra $5 million.

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But, just like in chess, there could be moves happening in the background that everyone doesn’t notice until it’s too late, and there’s always a chance Brady could be donning a new uniform in 2020 as a result.

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