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The most challenging season of Tom Brady's 23-year NFL career came to an end Monday night when the Buccaneers lost, 31-14, to the Cowboys in the wild-card round of the playoffs. Brady's decision to end last offseason's brief 40-day retirement to continue playing football cost him his 13-year marriage to supermodel Gisele Bundchen. The divorce was finalized at the end of October.

Brady had his first losing season in the NFL. The Buccaneers won a weak NFC South with an 8-9 record.

Father Time finally started catching up with the 45-year-old. He didn't come close to replicating his MVP-caliber 2021 campaign in which he threw for a league leading (and a career high) 5,316 yards and 43 touchdown passes. Brady broke his own NFL single-season records with 733 pass attempts and 490 completions this season. He was also third in the league with 4,694 passing yards.

Brady looked every bit of his age against the Cowboys. It was arguably the worst playoff game of his career. He only completed 53% of his eye-popping 66 pass attempts and was fortunate to only throw one interception. 

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Brady's contract history with Bucs

Brady was noncommittal on his future during his postgame press conference. He stated he was going to take things "one day at a time."

Brady is set to enter free agency for the second time in his career, as his contract expires March 15. He can't be prevented from hitting the open market. Brady's contract contains a clause prohibiting the Buccaneers from designating him as a franchise or transition player. 

The Buccaneers radically changed their approach to salary cap management after signing Brady to a fully guaranteed two-year, $50 million contract worth a maximum of $59 million with incentives as an unrestricted free agent in March 2020. Win-now mode personnel moves were constantly made with little regard to long-range planning. Salary cap obligations were consistently pushed into the future through a series of contract restructures with multiple players, including Brady. The bill will start coming due if Brady retires.

Brady freed up $19.3 million of 2021 salary cap room that March with a one-year, $27,941,176 contract extension, which helped the Buccaneers "keep the band together" to try to repeat as Super Bowl champions.

The extension included three voiding/dummy contract years (2023 through 2025), so his fully guaranteed $20 million fifth-day-of-the-2021-league-year roster bonus and $20 million signing bonus could be prorated over five years (through 2025) instead of over just two years (through 2022). Both of these salary components were each prorated on the salary cap at $4 million annually for these five years.

After Brady decided to play a 23rd season, his contract was reworked again last April. Instead of making $10,395,588 in 2022 on a $20,270,588 cap number, his compensation was raised to $15 million by essentially buying out the $4.5 million of incentives in his contract.

$13.88 million was converted to a roster bonus due one day after executing the new contract that would be prorated over the life of the contract, like a signing bonus, while a dummy/voiding 2026 contract year was added. The new dummy/voiding year allowed the roster bonus to be prorated on the salary cap at $2.776 million annually from 2022 through 2026. Brady's 2022 cap number dropped to $11.896 million in the process.

How Brady's decision impacts Buccaneers financially

If Brady retires

The Buccaneers will have $35.104 million of dead money, a salary cap charge for a player no longer on the roster, if Brady retires. The dead money would consist of $12 million in 2021 roster bonus proration (2023 through 2025), $12 million in signing bonus proration (2023 through 2025) and $11.104 million in 2022 roster bonus proration (2023 through 2026). 

An already difficult 2023 salary cap situation would get worse with Brady's $35.104 million of dead money. Assuming the 2023 salary cap is set in the $225 million neighborhood, Tampa Bay would have approximately a $52.5 million overage using NFLPA data under offseason accounting rules in which only the top 51 salaries (i.e.; cap numbers) matter. 

There is a way for Tampa Bay to get more favorable cap treatment with a Brady retirement. Brady and the Buccaneers would need to modify his contract so his dummy/voiding 2023 contract year is turned into a real contract year with his league minimum $1.165 million base salary as compensation. The voiding date for the 2024 through 2026 contract years could be pushed back from the last day of the 2022 league year (March 15) to the last day of the 2023 league year, or those three years could be turned into real contract years instead.

The Buccaneers would carry Brady with his new $11.941 million 2023 cap number until June 2 when his retirement would be processed and his $1.165 million base salary would come off the books. By waiting until June 2, the Buccaneers would be able to split the $35.104 million of dead money into $10.776 million in 2023 and $24.328 million in 2024. The $8 million of 2021 roster bonus proration from 2024 and 2025, the $8 million in signing bonus proration relating to 2024 and 2025, as well as the $8.328 million of 2022 roster bonus proration attributed to 2024 through 2026, wouldn't hit Tampa Bay's salary cap until 2024.

If Brady signs with another team

Brady playing a 24th season for another team would be the least desirable outcome for the Buccaneers from a salary cap standpoint. There wouldn't be any way to avoid Brady's $35.104 million of dead money being a 2023 cap charge. The $24.328 million of remaining bonus proration relating to his dummy 2024 through 2026 contract years would hit Tampa Bay's 2023 salary cap on March 15 when these years void. 

The Raiders are the most obvious team for Brady because of the Josh McDaniels connection and quarterback Derek Carr either being traded or released. McDaniels was Brady's quarterback coach and/or offensive coordinator for 13 of his 20 seasons with the Patriots. CBS Sports NFL writer Cody Benjamin identified several potential Brady landing spots earlier this week if he decides to keep playing football.

If Brady returns to Bucs

The Buccaneers reportedly want Brady to return should he keep playing. In a Brady return to Tampa Bay, an agreement would likely be reached a day or two before the current league year ends March 15, so the Buccaneers could avoid the $35.104 million cap charge from Brady's dummy contract years voiding.

Brady's voiding 2023 through 2026 contract year each have a $30 million base salary. $30 million for 2023 would be in line with the $87,795,588 Brady has made from his NFL player contracts during his three years with the Buccaneers, which have averaged just over $29.25 million per year.

$28.835 million of the $30 million could be a fully guaranteed roster bonus due a couple days after signing the new contract, leaving Brady with a $1.165 million base salary, his league minimum. The $30 million base salary would remain for the 2024 and 2026 contract years while a 2027 contract year at $30 million could be added. These four years could void on the last day of the 2024 league year. Brady's no-trade clause and the language preventing a franchise or transition tag that has been in his other Buccaneers contracts would continue to be included.

The $28.835 million would be prorated on the salary cap at $5.767 million annually for the five years (2023 through 2027). Brady's 2023 cap number would be $17.708 million. The components would be Brady's $1.165 million base salary, $4 million of 2021 roster bonus proration, $4 million of pre-existing signing bonus proration, $2.776 million of 2022 roster bonus proration and $5.767 million of new roster bonus proration.

Brady would prefer a roster bonus over a signing bonus. The Buccaneers wouldn't have rights of recoupment for any type of contract breach, including retirement, after the 2023 league year with the roster bonus.

The big drawback to having as much of Brady's 2023 compensation as possible being prorated is there would be $23.068 million of new dead money with Brady retiring after the 2023 season. The Buccaneers would have $47.396 million of dead money to contend with that most likely would be split into $16.543 million in 2024 and $30.853 million in 2025.

Final thoughts

No matter what Brady decides, he is going to be fine. Brady ending his career where it's abundantly clear that he hung on too long wouldn't diminish his legacy. He would still be a sure-fire first-ballot Hall of Famer and the greatest quarterback to ever play. 

Brady already has a great post-career transition in place. He will become Fox Sports' lead analyst on NFL games and work as an "ambassador" for the network with a focus on "client and promotional initiatives" once he permanently hangs up his cleats.

Brady's deal is reportedly worth $375 million over 10 years. It is the most lucrative contract in sports broadcasting history. The value of Brady's contract with Fox Sports is more than he has made from his NFL player contracts. None of Brady's NFL player contracts have averaged $37.5 million per year like his broadcasting deal.