Ideally, the New Orleans Saints would have signed 37-year-old quarterback Drew Brees to a contract extension to lower his league-high $30 million 2016 salary cap number before free agency started on March 9. A new deal would have given the Saints, who entered free agency with approximately $8.8 million of salary cap room, more flexibility to improve a 7-9 team coming off its second straight season without a playoff berth. Curiously, the Saints' big free agency move has been signing tight end Coby Fleener to a five-year, $36 million contract with $18 million in guarantees despite possessing a historically bad defense in 2015.

It has been quiet on the Brees contract front since Saints general manager Mickey Loomis shot down the notion that the nine-time Pro Bowler could be traded or released in January and subsequently declared his intention to sign him to a new deal in a Sirius XM NFL Radio interview. Head coach Sean Payton expressed optimism about quickly reaching an agreement with Brees in an NFL Network interview at last month's NFL Scouting Combine. Tom Condon, Brees' agent, in an appearance on the Rich Eisen Show last week, anticipated that contract talks would begin in a couple of weeks. This projected timing coincides with the NFL's Annual Meeting in Boca Raton, Florida, set for March 20-23. Loomis declined to answer questions about Brees' contract at LSU's Pro Day yesterday.

Brees appears to hold all of the cards in negotiations with the Saints. He is 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 and reset the league's pay scale. $10.85 million of his $19.75 million base salary became fully guaranteed without an offset on February 10.

Using a franchise tag on Brees in 2017 if he played out his contract would be too cost prohibitive. His franchise tag number will be $43.09 million, which is based on 144 percent of his 2016 cap number. Brees must decide whether to exploit his leverage with a new deal or take some sort of hometown discount in an effort to help the Saints improve the talent around him to try to become Super Bowl contenders again.

Should Drew Brees give the Saints a hometown discount? (USATSI)

The Tom Brady approach

Tom Brady became the NFL's highest-paid player (by average yearly salary) in 2010 with a four-year, $72 million extension. Since then, he has given the New England Patriots steep hometown discounts in contract dealings.

Brady's 2013 offseason renegotiation that freed up substantial cap room for the Patriots over the next two seasons was at 40 to 50 percent of his market value. He received $33 million, which was fully guaranteed, in the first two years of the renegotiated deal instead of the $30 million he was scheduled to make in the remaining two years of his old contract signed in 2010. The final three years of Brady's pact (2015 through 2017) for $24 million were guaranteed for injury at signing. These years also became guaranteed for skill (without an offset) by him being on New England's roster for the final game of the 2014 regular season. Right before those playoffs started, Brady gave up the skill guarantee in the three years. In exchange, $1 million was added to each of his remaining base salaries.

Brady, who turns 39 years old in August, recently agreed to a two-year extension for $41 million running through the 2019 season when he is 42. Prior to the extension, Brady was making $9 million and $10 million in 2016 and 2017, the last two years of the 2013 renegotiation, on $15 million and $16 million cap numbers. He received a $28 million signing bonus while lowering his 2016 and 2017 base salaries each to $1 million, which is $11 million more than he was scheduled to make over this time before the contract adjustment. Both salaries are guaranteed for injury but 2017 becomes fully guaranteed on the third day of that league year (approximately March 10, 2017). Since Brady's cap numbers are $14 million in each year, the Patriots are getting $1 million and $2 million of cap relief in 2016 and 2017.

Brady is underpaid by practically every measure. His new pact can be viewed as a four-year, $60 million deal. Another way to look at it is to focus on the new money Brady will receive through his 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. There is $71 million of new money over five new contract years for an average of $14.2 million per year.

Tom Brady's below-market deals have helped the Patriots remain a contender. (USATSI)

Likelihood of Brady approach

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

Brees would appear to be a good candidate to follow Brady's lead since he has made $154.683 million from his playing contracts during his 15 NFL seasons. But there are a variety of reasons why Brees is unlikely to do the Saints a huge favor with an extension, like Brady.

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 NFLPA's executive committee, so he likely understands how starting a trend of 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 with his contracts but would never an 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.

Recent developments in the quarterback market

Recent developments in the quarterback market will likely have more of a bearing on the Brees negotiations than Brady's contract maneuvers. Joe Flacco took advantage of the Baltimore Ravens' tight cap situation a couple of days after Brady's extension was first announced to replace Green Bay Packers quarterback Aaron Rodgers as the NFL's highest-paid player. Rodgers' five-year extension from 2013 averages $22 million per year, while Flacco signed a three-year, $66.4 million extension (for an average of $22,133,333 per year) with an NFL record $40 million signing bonus. The $37 million signing bonus Brees received in his 2012 contract had been the previous high.

$44 million of Flacco's deal is fully guaranteed at signing. His 2017 and 2018 base salaries of $6 million and $12 million are guaranteed for injury only. The Ravens pick up $6 million of immediate cap space with the extension as Flacco's 2016 cap number drops from $28.55 million to $22.55 million. Flacco is under contract six years for a total of $125 million.

Brees' agent, Tom Condon, surprisingly got Sam Bradford, who has never come close to living up to the potential that made him the 2010 NFL draft's first overall pick, a two-year, $35 million contract with $22 million fully guaranteed ($40.5 million maximum through salary escalators and incentives) to stay with the Philadelphia Eagles as the March 1 franchise/transition designation period was ending. Brock Osweiler left the Denver Broncos in free agency for a four-year, $72 million deal with the Houston Texans containing $37 million fully guaranteed. Most view Osweiler's contract as excessive for a quarterback with only seven career starts.

Joe Flacco leveraged the Ravens' cap woes into landing a new mega-deal. (USATSI)

The Tom Condon factor

Besides Brees, Condon represents several other prominent quarterbacks. Some of his quarterback clients are Bradford, Manning, Matt Ryan, Alex Smith, Matthew Stafford and the recently retired Peyton Manning, who is Eli's older brother. Condon typically negotiates strong quarterback deals that can be construed as having a player-friendly structure. For example, the five-year, $103.75 million extension Ryan received from the Atlanta Falcons in 2013 contained $42 million fully guaranteed at signing. Ryan also had the most money fully guaranteed within the first 12 months when the deal was consummated at $59 million.

Agents are supposed to work for the player, even though it may sometimes seem as if it's the other way around. In the typical player/agent relationship, a player will give his agent input about a contract on a big picture level initially but may not get involved in the process again until the final stages of a negotiation, if at all. Because of this dynamic, an agent is usually given wide latitude to negotiate a contract that he or she feels is in the client's best interest.

Left to his own devices, Condon will likely attempt to reclaim the signing bonus record while reinstituting Brees as the NFL's highest-paid player (by average yearly salary) like he accomplished with the 2012 contract. Condon couldn't make the younger Manning the league's highest-paid player with the New York Giants last year despite widespread speculation that was the veteran agent's goal. Manning's four-year, $84 million extension ranked him fourth in average year salary at $21 million per year. He tied Rivers with the most overall contract guarantees at $65 million. Manning's $68.5 million is the best three-year cash flow in the NFL.

Any type of discount will require Brees specifically instructing Condon to leave money on the table like the elder Manning did when he originally 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 down to four teams and picked his destination before having Condon commence negotiations instead of letting him leverage the considerable interest, which reportedly included a $25 million-per-year offer from the Tennessee Titans, into a blockbuster contract. Instead, he still briefly set the NFL salary bar with his five-year, $96 million deal, which lasted until Brees signed four months later.

The Saints' realistic best case scenario

It's probably just wishful thinking by the Saints that Brees will accept a contract at or below the same $20 million per year as his current contract instead of Condon insisting his client replace Flacco as the NFL standard. The salary cap was $120.6 million in 2012 when Brees signed his deal. An equivalent deal adjusted to the current $155.27 salary cap environment is approximately $25.75 million per year with almost $78 million in guarantees.

The best bet to get Brees to give the Saints any kind of financial break is with an extremely frontloaded contract where he receives a modest raise using Manning's deal with the Giants as a guide. A new contract could look like the following:

Signing Bonus: $40 Million ($14 Million with 30 days of execution; $14 Million payable in 17 equal installments over the regular season; $12 Million payable on 1/15/17)
Guaranteed money: $54.5 Million
Fully guaranteed at signing: $41.75 Million
New money total: $85 Million ($105 Million over 5 Years)
Contract length: 4 Years Extension
Average per year: $21.25 Million

Here's the contract breakdown:

Suggested contract for Drew Brees
Year Base Salary Workout Bonus Signing Bonus Proration Salary Cap Number Cash Flow
2016 $1,750,000 $250,000 $18,000,000 $20,000,000 $30,000,000
Guaranteed for skill, injury & salary cap
2017 $12,750,000 $250,000 $8,000,000 $21,000,000 $55,000,000
Guaranteed for injury; skill & salary cap on 3rd day of 2017 waiver period; no offsets
2018 $13,750,000 $250,000 $8,000,000 $22,000,000 $69,000,000
Guaranteed for skill, injury & salary cap on 3rd day of 2018 waiver period; no offsets
2019 $16,750,000 $250,000 $8,000,000 $25,000,000 $86,000,000
Guaranteed for skill, injury & salary cap on 3rd day of 2019 waiver period; no offsets
2020 $18,750,000 $250,000 $8,000,000 $27,000,000 $105,000,000
Guaranteed for skill, injury & salary cap on 3rd day of 2020 waiver period; no offsets

Making sense of the suggested contract

Four contract years are being added so the Saints can get the maximum cap benefit from signing bonus proration. The possibility of there being a significant cap charge for Brees if he is released before completing the contract when he is 41 shouldn't be a sticking point to reaching an agreement since the Saints consistently push the envelope with their aggressive style of cap management.

Brees' cap numbers are more manageable than in his 2012 contract. His $20 million cap number for the upcoming season would be the eighth-highest among quarterbacks. Brees would have the fifth-highest quarterback cap charge for 2017. His original cap numbers in 2014 ($26.4 million) and 2015 ($27.4 million), the last two years of his existing contract, are greater than the cap charges in the last two years of the suggested contract.

The 250,000 annual workout bonus is consistent with Brees' current contract. The 2018 through 2020 salary guarantee dates mimic his existing 2015 and 2016 contract years. Deferring $12 million of signing bonus until January shouldn't be an issue since that's what happened in Brees' current deal. The payment date was January 15, 2013. $30 million in 2016 would also be $1 million more than Flacco is making this year because $15 million of his signing bonus is payable on March 15 in 2017.

Brees' cash flow is in line the Manning extension Condon negotiated with the Giants. Manning is at the same $55 million as Brees after the first two years of his deal and $68.5 million through three years. Brees' $69 million would narrowly eclipse Manning for the NFL's best cash flow over three years.

The concept could still work if Brees wanted to be the league's highest-paid player. For example, an extra $4 million could be allocated over the 2017 through 2020 contract years, which would make the cap numbers at the end of the deal more burdensome.

Possible uses of extra cap room

The Saints would pick up $10 million of much needed cap room from the suggested contract since the team is only approximately $2.575 million under the cap. Another $2.25 million of cap space will be gained on June 2 when cornerback Brandon Browner's post-June 1 designation takes effect.

The new cap room could be used to address a porous defense that has been neglected thus far in free agency. The Saints were last in the NFL in points allowed (29.8 per game), and next to last in total defense (413.8 yards per game) in 2015. 45 touchdowns were given up through the air, which is the most ever in an NFL season. Opponents also had a 116.2 passing rating versus the Saints, another NFL record.

Improving the pass rush is a priority according to Payton. Outside of Greg Hardy, whose considerable baggage is hindering him getting a job, there is slim pickings left in free agency for edge rushers now that Los Angeles Rams cap casualty Chris Long has agreed to terms with the Patriots. 

The Saints have expressed an interest in defensive tackle Nick Fairley, who would provide an interior pass-rushing presence. When Fairley's market didn't develop as he expected on the open market last year, he quickly took a one-year deal from the Rams in which he made $5,218,750. Louisiana native Jason Hatcher is also on the Saints’ radar screen. The Washington Redskins opted to let the 10-year veteran go instead of paying his scheduled $6.5 million 2016 salary.

The Saints have already kicked the tires on middle linebacker James Laurinaitis, who was released by the Rams at the same time as Long. The three-year, $21 million deal Derrick Johnson recently signed to stay with the Kansas City Chiefs may be a salary benchmark for Laurinaitis, whose last contract averaged $8.3 million per year. According to ESPN's Adam Schefter, Craig Robertson, who started 37 games with the Cleveland Browns during the last four seasons, will be brought in for a visit this week. He should be cheaper than Laurinaitis.

Cornerback is another area that may need to be upgraded with the uncertainty surrounding Keenan Lewis and the release of Browner from the three-year, $15 million deal he signed last offseason. Lewis was limited to six games in 2015 because of a hip injury and has had multiple surgical procedures since the injury occurred. Prince Amukamara established the salary ceiling for short-term deals by signing for $5.5 million (worth a maximum of $6 million through incentives) to play this season only with the Jacksonville Jaguars. The Saints might be able to sign Leon Hall, Jerraud Powers or Greg Toler for less than Browner's deal. Tracy Porter re-signed with the Chicago Bears for $12 million over three years.

Jahri Evans being released after refusing to take a pay cut created a hole at right guard. Geoff Schwartz could be a moderately-priced option. Louis Vasquez is also available.

A veteran presence at wide receiver could also be a consideration after the departure of Marques Colston, the franchise's all-time leading pass catcher. The New England Patriots released former LSU Tiger Brandon LaFell from a three-year deal averaging $3 million per year. He's destined to take a pay cut on his next contract. James Jones would like to remain in Green Bay but that may not be possible with Jordy Nelson coming back from an ACL tear and the presence of younger wideouts, Jeff Janis and Jared Abbrederis. The 31-year-old WR led the Packers in receptions, receiving yards, touchdown catches and yards per catch while making his league minimum $870,000.

Final thoughts

It may make sense for the Saints to re-think their plans for Brees if Condon's expected contract demands are viewed as outrageous or an agreement isn't reached prior to NFL draft, which begins on April 28. At this point, the Saints will be relying primarily on the draft for an infusion talent since the window of opportunity to improve through free agency will be gone for all intensive purposes. Although Brees isn't showing signs of slowing down, taking a wait-and-see approach on a new deal could become more of a consideration as time goes on.


Joel Corry is a former sports agent who helped found Premier Sports & Entertainment, a sports management firm that represents professional athletes and coaches. Before his tenure at Premier, Joel worked for Management Plus Enterprises, which represented Shaquille O'Neal, Hakeem Olajuwon and Ronnie Lott.

You can follow him on Twitter: @corryjoel | You can email him at jccorry@gmail.com