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For the first time in his 20-year career, Tom Brady is poised to become a free agent.

On March 17 at 4 p.m., his contract with the Patriots will expire. On the last day of the 2019 league year, he’ll become an unrestricted free agent.

Beginning March 16, teams are allowed to contact the agents of players who will become free agents upon the beginning of the new league year.

Here’s a very simplified version of what could happen:

  • Brady re-signs with the Patriots before his contract expires. He avoids free agency and it allows the Patriots to spread the $20.25 million signing bonus he agreed to last August over three years (2019, 2020 and 2021), which helps with salary-cap ramifications.
  • Brady re-signs with the Patriots after March 18. If the contract is allowed to expire, the $13.5 million Brady was to be paid would be accelerated to the 2020 season, meaning the Patriots would need to have that money included in his new contract.
  • Brady signs a deal with a new team.
  • Brady changes course and decides to retire.

We’re tracking each move and development between now and March 17, or when Brady signs a contract — plus anything else you might need to know.

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Tuesday, Feb. 25 | 22 days until March 17

ESPN’s Adam Schefter said on “Get Up” this morning that the Tom Brady situation could gain some clarity later this week.

NFL teams are able to apply the franchise tag to players beginning this week. One question in the air: Will the Titans franchise Ryan Tannehill?

“If they put the franchise tag on Ryan Tannehill,” Schefter explained, “That would essentially take them out of any talks or discussions for Tom Brady.”

Schefter said we should “get a glimpse of what the Titans’ thinking is” and if they’re looking to get in on the Brady sweepstakes.

Monday, Feb. 24 | 23 days until March 17

Ian Rapoport of the NFL Network reports that the Patriots are expected to meet with Tom Brady’s longtime representative Don Yee during the NFL Combine in Indianapolis this week.

Tuesday, Feb. 18 | 29 days

Finally, we know what Ben Affleck heard. And he hasn’t heard much.

The movie star with local ties told ESPN’s “Get Up” that he shares a text group with Tom Brady and friend Matt Damon. When the two actors asked Brady what the plan was, all they got back was 🤷‍♂️.

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“Me and Matt texted him, and said, ‘What’s the deal? You going or you staying?’ And this is what we got back: an emoji,” Affleck said, doing his best impression of the shrug emoji.

Wednesday, Feb. 12 | 35 days until March 17

Will he stay? Will he go? Yes, it’s the question on every Patriots fan’s mind. But, as Ben Volin lays out, all the speculation likely won’t lead one to an answer. Heck, even Tom Brady probably doesn’t know what will happen.

That’s because deadlines matter in this situation. The deal won’t come together until the clock is ticking.

FOXBORO, MA - JULY 27, 2019: Nick Caserio director of player personnel speaks with the media before the New England Patriots training camp at Gillette Stadium in Foxboro, MA on July 27, 2019. (Craig F. Walker/Globe Staff) section: Sports reporter:
FOXBORO, MA - JULY 27, 2019: Nick Caserio director of player personnel speaks with the media before the New England Patriots training camp at Gillette Stadium in Foxboro, MA on July 27, 2019. (Craig F. Walker/Globe Staff) section: Sports reporter:Craig F. Walker/Globe Staff

In addition, the Patriots and director of player personnel Nick Caserio agreed to a contract extension that will keep the executive with the team for a 20th season.

Retaining Caserio offers continuity, explains Ben Volin. The Patriots have suffered several coaching and personnel losses the last few years, including Matt Patricia, Brian Flores, and several assistant coaches, plus current NFL GMs Bob Quinn and Jon Robinson, and several scouts on the personnel side.

But Bill Belichick, Josh McDaniels, and now Caserio — who is essentially the general manager — have remained, keeping the key pieces in place. This may make it easier to convince Brady to return for another season.

Monday, Feb. 10 | 37 days

Patriots owner Robert Kraft made an appearance at an Oscar party on Sunday in Los Angeles, and of course he was asked what he wants Tom Brady to do.

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“You know what I want."

Meanwhile, on the west coast, Phillip Rivers and the Chargers announced that Rivers would become a free agent instead of returning to the team for which he’s played for his whole 16-year career. Does that pave the way for Brady to head to Los Angeles?

Friday, Feb. 7 | 40 days

One thing is for certain: Tom Brady has had plenty of time to up his social-media game as of late. On Friday, he didn’t let the chance go by to take a shot at former rival Peyton Manning and his golf game.

Which begs the question: Is Tom Brady becoming a certified Internet troll? Chad Finn lays out the facts in a column from this week.

Wednesday, Feb. 5 | 41 days

Tom Brady took to Instagram to answer some questions about his fitness routine. Fans took the opportunity to ask about his future. (He didn’t take the bait.)

Tuesday, Feb. 4 | 42 days

Maybe this will convince Tom Brady?

Monday, Feb. 3 | 43 days

The Daily Mail spotted moving trucks outside the Brookline home of Tom Brady and Gisele Bundchen. Brady and his family are reportedly spending part of the offseason in New York City while they try to sell their Massachusetts mansion.

Sunday, Feb. 2 | 44 days

Tom Brady may have had some veiled references to his upcoming free agency in a Super Bowl commercial he appeared in for streaming service Hulu.

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View this post on Instagram

I have an important announcement #ad

A post shared by Tom Brady (@tombrady) on

“But me? I’m not going anywhere,” he spoke to the camera after making his pitch for consumers to sign up for Hulu.

Brady, Bill Belichick and the Patriots still dominated the conversation in Miami on Super Bowl Sunday. A number of former players were on hand for the NFL 100 pregame celebration.

View this post on Instagram

Pats Nation ❤️

A post shared by Tom Brady (@tombrady) on

After the Chiefs’ win in Super Bowl LIV, oddsmakers immediately began looking to next season.

Many sports books have odds on where Brady will end up, and Sports Betting Dime put it at 2-3 — the mostly likely scenario — that Brady remains a Patriot.

Thursday, Jan. 30 | 47 days

Tom Brady to the Titans?

That rumor was quickly debunked, but Brady played into the discourse with his cryptic social-media post on Thursday evening.

The post sent fans everywhere into panic mode. What could it mean?! (Turns out, it’s for a Super Bowl ad.)

Wednesday, Jan. 29 | 48 days

If you’re the betting type, you’ll love this news: The latest odds from DraftKings on where Tom Brady will start in 2020 have New England as the clear favorite. (Other teams in the top three: Chargers and Colts.)

Tuesday, Jan. 28 | 49 days

Rob Gronkowski weighed in on Tom Brady’s future, and he thinks his former QB has a right to test out that free agent market.

I truly believe that he deserves the opportunity to go explore — to see what’s out there," he told the Globe’s Jim McBride. "He’s been playing for so long and just the way that he’s been playing — just the level that he’s been playing at — he definitely deserves an opportunity to go out there and test the market.’’

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Where in the world is Brady, anyway? Manhattan, it seems.

NFL Network’s Mike Girardi reports that Brady, his wife Gisele and their children are living in New York City right now. Their home in Brookline has been on the market and remains unsold.

Monday, Jan. 27 | 50 days

Now we know what Joe Montana thinks.

The NFL legend, who began his career in San Francisco and finished it in Kansas City, knows how hard it is for a veteran to adjust to a new team.

That’s why he’s telling Tom Brady to stay with the Patriots.

“It’s not easy to go to another team and get accepted, no matter how much success you’ve had and how many years you’ve played,” Montana told NFL Media. “They still want to see you come in and be the same player and be that loyal to them as you were to the other team you just left. So, it’s not easy [for] guys looking at that change, especially at the quarterback position.”

Sunday, Jan. 19 | 58 days

Tom Brady tells Westwood One he’s still interested in playing in 2020, and said he’s going to embrace whatever the future brings “with open arms.”

And Brady’s former backup, Jimmy Garoppolo, is headed to the Super Bowl after the 49ers beat the Packers, 37-20, in the NFC Championship game.

One more thing of note: Phillip Rivers is moving to Florida.

The quarterback is a free agent and, after 16 seasons with the Chargers, it appears the team is moving on from him. Rivers told ESPN that it was time to get closer to family.

“What this means football-wise is to be determined but it was time for us to move back closer to home,” Rivers said.

Why does this matter when it comes to tracking Tom Brady? Brady is a California native and Los Angeles has been a rumored destination if he were to leave the Patriots. This opens up a clear path.

Saturday, Jan. 18 | 59 days

Tom Brady was spotted talking with Las Vegas Raiders owner Mark Davis on Saturday at a UFC fight in Sin City.

He wasn’t the only NFL star in attendance -- Christian McCaffrey, Myles Garrett and Baker Mayfield were also there -- and he also spoke with Mass. native and UFC president Dana White.

White had some thoughts on Brady’s impending free agency:

“If that dude isn’t playing for Boston, he’s playing here."

Sunday, Jan. 12 | 65 days

The Browns choose to hire Kevin Stefanski, offensive coordinator of the just-bounced Vikings, instead of Josh McDaniels for their open head-coaching position.

What does that mean for Tom Brady? Well, it means that Tom Brady may be more likely to return if he’s not in a position where he’ll have to form a new relationship with a new coordinator -- who might have a new offense. Ben Volin explains the details.

From Jan. 12: Why signing Tom Brady to a multi-year deal makes sense for the Patriots

Saturday, Jan. 11 | 66 days

Jimmy Garoppolo celebrates the 49ers' win on Saturday.
Jimmy Garoppolo celebrates the 49ers' win on Saturday.Ben Margot/Associated Press

Two familiar names are one step closer to the Super Bowl after Saturday’s divisional games.

Jimmy Garoppolo and the 49ers are headed to the NFC Championship game after beating the Vikings, 27-10, at Levi’s Stadium.

Related: 49ers fans love Jimmy Garoppolo. Like, really love him

Then, Mike Vrabel’s Titans stunned prohibitive favorite Baltimore in the late game, winning 28-12.

Meanwhile, Josh McDaniels is in a holding pattern over the Browns job.

Friday, Jan. 10 | 67 days

Josh McDaniels spent more than seven hours interviewing for the Browns head coaching job. He and his wife Laura were flown to Cleveland by team owner Jimmy Haslam.

He was the final candidate to interview for the final NFL job open during this hiring cycle.

Meanwhile, Jim McBride took stock of the Patriots roster. Here’s a look at how it stood on Jan. 10.

Thursday, Jan. 9 | 68 days

Joe Judge is introduced as the new Giants coach. He divulges the only piece of advice Bill Belichick offered up: “He told me to just be yourself, and that’s all I know how to be.”

Meanwhile, Ben Volin plays a what-if game: What if Tom Brady leaves? Who would he play for?

Here are 14 teams, with a reason he’d consider and a reason he wouldn’t.

Wednesday, Jan. 8 | 69 days

Brady posts on Instagram: “In both life and football, failure is inevitable. 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.”

What does that mean? It confirms his intentions to play football in 2020, just like he said after the Patriots’ loss to the Titans.

Tuesday, Jan. 7 | 70 days

Matt Rhule and Joe Judge both got new jobs. Josh McDaniels does not.

The Patriots offensive coordinator is scheduled to have interviews with the Panthers on Tuesday and the Giants on Wednesday. Instead, the Panthers chose to hire Rhule from Baylor; a few hours later, the word trickles out that the Giants are finalizing a deal with Patriots’ special-teams coordinator and wide receivers coach Joe Judge.

With Mike McCarthy off to Dallas, that leaves one option for McDaniels: the Browns. McDaniels is scheduled to interview with them on Friday. Or, he could opt to sit this cycle out, and try for another head-coaching job next season.

Any way you look at it, the Patriots will once again need to do some rebuilding on the coaching staff. Judge, 38, has been with the team since 2012 and received wide-receiver duties this season to help prepare him to step into a head role.

“Joe could probably coach any position on the field,” Bill Belichick said about him last year. “He does an excellent job of teaching players. He thinks quickly, the game comes easily to him. He understands concepts and adjustments and fundamental techniques. That’s the mark of a good coach.”

Now, Judge will be tasked with helping to develop Daniel Jones as he enters his first season as full-time starter in New York.

Monday, Jan. 6 | 71 days

Robert Kraft, speaking to NBC Sports’s Peter King, knows exactly what he wants when it comes to Tom Brady’s future: “My hope and prayer is number one, he plays for the Patriots. Or number two, he retires.”

Kraft lauded his quarterback just a day after Bill Belichick said “nobody respects Tom more than I do” but also said that the process is “not a one-way street.”

What does all of this mean? Here’s a breakdown from Ben Volin, who reads between the lines.

Sunday, Jan. 5 | 72 days

Bill Belichick found himself in an unusual place on a Sunday morning in early January: behind the podium at Patriots HQ for his end-of-season press conference.

The Patriots head coach wouldn’t say much about the way the Patriots plan to approach Tom Brady’s free agency.

“Everybody’s situation on the team is different. There are not two that are exactly the same, but future is the future for all of them, just like it is for Tom and anybody else you want to bring up,’’ said Belichick. “Certainly, Tom’s an iconic figure in this organization and nobody respects Tom more than I do.’’

The Patriots’ first-round draft pick was also determined on Sunday. They will pick No. 23.

Saturday, Jan. 4 | 73 days

There was nothing a hype video could do to save the Patriots in 20-13 loss to the Titans that ended their season. It was the first time the Patriots had to play in the wild-card round since 2009.

After the game, Tom Brady addressed the biggest question in his postgame press conference: How likely is he to retire? “I would say it’s pretty unlikely, hopefully unlikely.”

There you have it.

But if he continues to play, will it be with the Patriots?

“I don’t know what the future looks like,” Brady said Saturday night. “I’m not going to predict it.”


Katie McInerney can be reached at katie.mcinerney@globe.com. Follow her on Twitter at @k8tmac.