A fairytale swansong with hometown team the San Francisco 49ers had been touted, while the Los Angeles Chargers, Indianapolis Colts, Miami Dolphins and Denver Broncos were also reportedly in the mix.
However, Tampa Bay will become veteran quarterback Brady's new home after 20 incredible seasons in Foxborough.
From six Super Bowl titles to a team without a playoff appearance since 2007, Brady will reportedly earn $30million per season on a two-year contract with Bruce Arians' Bucs.
But why did the Buccaneers turn their backs on former number one pick Jameis Winston for a 42-year-old quarterback? Well the writing was on the wall…
October 13, 2019 – Arians on Winston: He has a habit of trying to be Superman
Now an unrestricted free agent and with starting options running out, Winston frustrated Bucs head coach Arians throughout the 2019 campaign.
After throwing five interceptions and managing two fumbles in a 37-26 loss to the Carolina Panthers in London, Arians had some words for the 2015 number one draft pick.
"Throw the damn ball away. He had avoided one [turnover after losing the ball], you might have avoided two, but you aren't throwing it anywhere to a receiver. Throw it away," Arians told the media after the game. "He has a habit of trying to be Superman. That's been a problem in the past.
"The fumbles haven't occurred this year until today. But, again, trying to make something out of nothing. It's just a matter of knowing when to quit on a play."
December 4, 2019 – Arians not ready to decide on Winston's future
Arians was noncommittal on Winston being Tampa Bay's quarterback after 2019.
Amid a difficult season, Arians was asked if he would throw his support behind Winston if quizzed by the Bucs' hierarchy and he told reporters: "I'm gonna pass on that one. I'm gonna wait until the end of December."
"There's been really, really, really good and there's been some really, really bad," Arians added. "I'm gonna pass until it's over and then we'll make a decision."
December 21, 2019 – Winston throws four picks
Winston threw four interceptions as the Houston Texans recorded a 23-20 road win over the Buccaneers to seal the AFC South title.
Quarterback Winston completed 25 of his 48 passing attempts for 335 yards, throwing one touchdown with his four picks.
On the day when it was reported the team had decided to retain his services for next season, Winston made the worst possible start by throwing a pick-six to Texans cornerback Bradley Roby on his first attempt and it did not get much better from there.
December 29, 2019 – Winston backs himself despite making unwanted NFL history
Winston insisted "I'm going to be the best" despite making unwanted NFL history against the Atlanta Falcons.
Winston became the first player to throw for at least 30 touchdowns and 30 interceptions in a season as the Buccaneers ended their campaign with a 28-22 overtime loss.
He joined the dubious 30-30 club after he was pick-sixed by Falcons linebacker Deion Jones on the first play of overtime in Tampa.
Winston – who became the eighth quarterback in league history to throw for 5,000 yards in a season – said: "I'm focused on how I can get better. I know if I eliminate those, I'm going to be the best. Bar none. You'd better check your sheet.
"If you look at the numbers, I'm balling. I've got to stop giving the ball to the other team. It's not a trick question. I know if I eliminate those [interceptions], I'm going to be the best, bar none."
Arians added: "You look at it and there's so much good and so much outright terrible. We got to weigh that and see what happens."
December 30, 2019 – Arians says Bucs can win without Winston
"[If] we can win with this one, we can definitely win with another one too," Arians told reporters. "We're going to have this defense."
Pressed on Winston's future heading into the offseason, Arians said: "It will be a while. I would think in a few weeks we will have a decision on which way we want to head. Will we let it out? Probably not. Because you lose your leverage on that one too. So it's 'stay tuned.'"
"Well, free agency, who's available?" Arians added. "What's behind door number two? That's the first question. Then as you evaluate for the draft, that's another question. Are they better than what you have? Then you evaluate and that's when you make your decisions."
February 26, 2019 – Arians names Brady as option
Speaking at the NFL scouting combine, Arians said: "As a head coach, you have to decide. Is there a better option?"
Pressed on free agency, Arians reeled off some names to reporters.
"Tom Brady. Philip [Rivers] is another guy. We'll see," he said.
"When those dominoes start falling, other guys are going to be on the market. I don't want to drag it out very long. It's one thing I want to get done soon."
March 16, 2020 – Bucs pass on tagging Winston
After throwing for 5,109 yards in 2019, the Buccaneers opted against using the franchise tag on Winston.
Instead, Tampa Bay used it to keep Shaquil Barrett from becoming a free agent.
March 17, 2020 – Brady announces Patriots exit
"I don't know what my football future holds but it is time for me to open a new stage for my life and career. I thank you from the bottom of my heart and I will always love you and what we have shared - a lifetime full of fun memories," Brady wrote in part via Twitter as he bid farewell to the Pats.
March 20, 2020 - Bucs arrival announced by Brady
Brady confirmed he would be continuing his career with Bucs. In an Instagram post, he wrote: "Excited, humble and hungry ...if there is one thing I have learned about football, it's that nobody cares what you did last year or the year before that...you earn the trust and respect of those around through your commitment every single day.
"I'm starting a new football journey and thankful for the Buccaneers for giving me an opportunity to do what I love to do. I look forward to meeting all my new team-mates and coaches and proving to them that they can believe and trust in me...
"I have always believed that well done is better than well said, so I'm gonna not gonna say much more - I'm just gonna get to work!"