Drew Brees, who turned 39 on Jan. 15, is headed toward free agency. The quarterback might have thrown his last pass in a Saints uniform, although he has reiterated his desire to end his career in New Orleans after a stunning 29-24 playoff loss to the Vikings, when Minnesota's 61-yard walk-off touchdown thwarted his team's 17-point second-half comeback. 

The Saints made the playoffs for the first time since 2013 as NFC South champions after three straight seasons with a 7-9 record. Both sides were content in letting Brees' contract play out. Reaching a new agreement might not be a smooth process for a variety of reasons.

How the Saints and Brees got to this point

Brees held all of the cards during negotiations in 2016, when he was entering the final year of the five-year, $100 million deal he signed in 2012 to become the NFL's first $20-million-per-year player. Using a franchise tag on Brees in 2017 if his contract expired was going to be too cost prohibitive. His franchise-tag number would have been slightly over $43 million. The Saints also needed to lower Brees' league-high $30 million 2016 salary-cap number.

Brees signed a one-year contract extension for $24.25 million at the beginning of the 2016 season. The contract contained a $30 million signing bonus while being structured with 2018-20 contract years that automatically void on March 14, the last day of the 2017 league year. The inclusion of the three fake years permitted the Saints to prorate the $30 million over five years for salary cap purposes, instead of just two years. If these dummy years void, the Saints will have an $18 million cap charge during the 2018 league year relating to Brees' signing bonus, regardless of where he plays next season.

Brees was given a no-trade clause. More importantly, his contract also contains language preventing the Saints from designating him as a franchise or transition player. From a practical standpoint, the voiding date eliminates the possibility of Brees being given a franchise or transition tag since it's after the designation period ends on March 6.

The Tom Brady way

Brees must decide whether to exploit his leverage in an effort to remain in New Orleans or take some sort of hometown discount, like Tom Brady has done, to increase his chances of becoming a multiple Super Bowl champion before he retires by allowing the Saints to assemble a more talented roster than otherwise possible.

Brady started taking an unusual approach to his contracts in 2013, when he first renegotiated the 2010 extension which made him the NFL's highest-paid player at $18 million per year. He began consistently giving the Patriots hometown discounts instead of driving the market.

Brady's third renegotiation since signing the 2010 deal, in March 2016, added two years for $41 million running through the 2019 season, when he will be 42 years old. This 2016 renegotiation covers four years for total of $60 million. The new money Brady will receive through his multiple contract maneuvers compared to what he would have gotten had he played out his 2010 contract, which was set to expire after the 2014 season, is $71 million over five new contract years for an average of $14.2 million per year.

Being dramatically underpaid has been rewarding for Brady on the football field. Brady has gotten two more Super Bowl rings since starting this process. He's in excellent position to get a sixth league championship given that the Patriots are favorites to win Super Bowl LII.

However, Brady hasn't started a trend among upper-echelon quarterbacks by taking a discount. Eli Manning, Philip Rivers and Ben Roethlisberger signed lucrative extensions in 2015 as 33- and 34-year-olds heading into a contract year.

Likelihood of the Brady way

Brees would appear to be a good candidate to follow Brady's lead since he has made close to $200 million from his playing contracts during his 17 NFL seasons. He wasn't shown any inclination in the past to give the Saints a discount, although he didn't fully exploit the tremendous leverage he had when signing the 2016 extension. Nonetheless, Brees' current contract made him the NFL's second-highest-paid player by average yearly salary when signed, behind only Colts quarterback Andrew Luck's $24.562 million.

Acrimonious negotiations as a franchise player in 2012 led to Brees filing and winning a grievance against the Saints clarifying whether franchise tags applied across teams or were specific to teams. Brees was a named plaintiff in an antitrust lawsuit against the NFL during the 2011 lockout. As a part of the lawsuit settlement talks, he wanted an exemption from the franchise tag for the rest of his career but eventually relented.

Brees is also a former member of the NFL Players Association's executive committee, so he likely understands how undercutting the marketplace could potentially have a negative impact on the contract negotiations of other players. The NFLPA probably hasn't been happy with Brady's willingness to be so accommodating toward the Patriots, but would never express a negative opinion publicly about the contract dealings of such a prominent player. Given the history between the NFLPA and Brees, the union would likely try to discourage him from doing the same thing if it had knowledge of his intentions beforehand.

Brees' choice of representation, Tom Condon of CAA Sports, has a tendency to drive a hard bargain when circumstances allow it. Condon, who represents several prominent passers in addition to Brees (Sam Bradford, Eli Manning, Matt Ryan, Alex Smith, Matthew Stafford, etc.), typically negotiates strong quarterback deals that can be characterized as having a player-friendly structure. For example, he reset the NFL pay scale with the five-year, $135 million extension he negotiated for Stafford, the Lions' signal caller, during the preseason. Stafford's deal has a league-record $92 million of overall guarantees. His $50 million signing bonus is the largest ever for an NFL player. The $60.5 million fully guaranteed at signing is also an NFL record.

Any type of discount will require Brees specifically instructing Condon to leave money on the table, like Peyton Manning did when he signed with the Broncos in 2012 after the Colts released him. Twelve teams reportedly inquired about Manning once he became available. Manning narrowed his choices to four teams and picked his destination before having Condon commence negotiations instead of letting him leverage the considerable interest in him, which reportedly included a $25 million per year offer from the Titans, into a blockbuster contract. He still briefly set the NFL salary bar with his five-year, $96 million deal, which lasted until Brees signed four months later.

Beware of Father Time

The Saints would be justified in being reluctant to commit to Brees beyond the 2018 season given his age, despite him previously expressing a desire, just like Brady has, to play into his mid-40s. Although Brees threw for fewer yards (4,334) and touchdowns (23) than he has in any season since joining the Saints in 2006, he isn't showing many signs of slowing down. The Saints finally developed a running game to complement Brees thanks to taking Alvin Kamara, a leading candidate for NFL Offensive Rookie of the Year, in the third round of the 2017 NFL Draft. Brees set an NFL record by completing 72 percent of his passes this season and was second in the league with a 103.9 passer rating. He was also named to the Pro Bowl for the 11th time in his career.

Brees demonstrated that he was still fully capable of winning a game with his arm by leading the Saints to a 31-26 victory over the Panthers in the wild-card playoff round, when the rushing attack was shut down. He was brilliant against the Vikings in the second half while erasing the 17-point deficit. In the final two quarters, Brees completed 17 of 22 passes for 177 yards with three touchdowns.

Typically, there isn't a gradual decline with older quarterbacks. The drop-off occurs rapidly, as was the case with Brett Favre and Peyton Manning. Father Time snuck up on both of them like a thief in the night. Brees can point to Brady, who is about a year and a half older, doing a better of fighting the clock than any quarterback in league history. Brady is having the finest season ever for a quarterback after turning 40. It will be a mild surprise if, in a couple of weeks, he doesn't win his third MVP award.

Brady, who will be 41 in August, is approaching uncharted territory. A quarterback has never performed at an extremely high level after reaching that age.

A potential compromise

The Saints and Condon must have a new Brees deal in place before 4 p.m. ET on March 14 to keep the $12 million of signing bonus proration in his fake 2019 and '20 contract years from becoming a 2018 league year cap charge. There's more incentive for the Saints, but it might make sense for both sides to go year-to-year since Father Time is undefeated and Brees doesn't want to leave where 2018 is converted into a real contract, with the voiding of the '19 and '20 contract years delayed until the last day of the 2018 league year in March 2019. The no-trade clause and franchise/transition tag prohibition would likely have to continue also.

The Cardinals and Larry Fitzgerald, who represents himself, did something similar in November. Fitzgerald's contract, which was set to void five days after Super Bowl LII on Feb. 9, was negotiated into a real year in 2018 by eliminating the voiding mechanism while agreeing to a salary for next season.

Brees' fake 2018, '19 and '20 years have $22 million, $21 million and $20.75 million salaries with $28 million, $27 million and $26.75 million as the associated cap numbers. A $22 million salary in 2018 wouldn't be unreasonable considering Brees is in the twilight of his career, though Condon isn't going to think a pay cut is warranted.

It wouldn't be surprising if Condon insisted that Brees regain his place in the league's salary hierarchy upon signing. This would at least mean a one-year deal for 2018 in the neighborhood of $26.5 million, with Condon knowing that any extension he does for Ryan will exceed Stafford's, a long-term deal for Kirk Cousins would also likely surpass Stafford's and a new Aaron Rodgers deal would reset the market. The salary cap was $155.27 million when Brees signed his extension. An equivalent deal, assuming the 2018 salary cap is set at the $178.1 million high end of projections, would be just over $27.75 million next season.

Brees' cap number would be approaching the almost $34.5 million it will take for the Redskins to use a franchise tag on Cousins for a third time because of the $6 million of signing bonus proration from the 2016 extension. It would probably be better for the Saints to put a majority of Brees' 2018 compensation in a roster bonus due a few days after signing to avoid adding to the $18 million of bonus proration from the three fake years.

A two-year deal where voiding doesn't occur until 2020 also wouldn't be out of the question, thanks to Brady defying the odds as a 40-year-old this season. A portion of Brees' 2019 money being fully guaranteed at signing with the remainder becoming fully guaranteed a few days after the waiver period started that February, as in Brees' 2012 contract, would be something Condon would likely push for if a strict year-to year concept isn't utilized. The average yearly salary would not be dramatically affected with either contract length.

Final thoughts

It's hard to imagine that Brees won't be in a Saints uniform next season. The Bills, Broncos, Cardinals and Redskins (assuming Cousins leaves) would be potential options if there's a parting of the ways. The Saints provide Brees with the best chance to win another Super Bowl ring because of the infusion of talent from a stellar 2017 draft. That is, unless the Jaguars aren't sold on Blake Bortles playing 2018 for his $19.053 million fifth-year option.