Odds Favor Drew Brees Retiring After 2020 NFL Season

• Saints quarterback Drew Brees is favored to retire after the 2020 season (-150)
• The 41-year-old future Hall of Famer signed a two-year, $50 million contract in March
• Find out below if we think the best bet is Brees calling it quits

New Orleans Saints quarterback Drew Brees is a slight favorite to retire after the 2020 season (-150) vs a return in 2021 (+110).

The 41-year-old — who will be a enshrined in Canton as a first-ballot hall-of-famer — signed a two-year, $50 million contract in March. A big reason why he has not retired yet is because New Orleans has suffered heartbreaking defeats in the playoffs three straight seasons.

Will Drew Brees Retire After the 2020 Season?

Odds taken Sept. 11

Brees, who is entering his 20th season in the NFL, made headlines this week saying he is “on borrowed time.”

"I'm on borrowed time. I got nothing to lose. I'm turning it loose and letting the chips fall where they may." – Drew Brees on his mindset heading into the season: pic.twitter.com/dzEePn58ZM

— Jori Parys (@JoriParys) September 9, 2020

If that isn’t a tell, I’m not sure what is. And while there may have been some uncertainty if Brees would even return this season, he ultimately inked the deal. The team also extended do-it-all backup Taysom Hill to a two-year, $21 million deal. That’s a lot of money at one position (not to mention third-string QB Jameis Winston).

So, while Brees is under contract for two more seasons with the Saints, he also reportedly signed an agreement with NBC Sports to become an NFL analyst whenever he decides to hang it up. Smart man.

Saints head coach Sean Payton even suggested earlier this year that this would be Brees’ “final season.” But the coach later called himself a “big dummy” for his word choice, saying he doesn’t know when Brees plans to retire. Sure. Is there a more simpatico player-coach relationship in the league than Payton-Brees?

All signs clearly point to Brees riding off into the sunset after the 2020 season is over. But what if his last game this season ends in injury or defeat? Therein lies the rub. Let’s handicap each side of the retire/return coin and make a pick.

Groundhog Day

The Saints have won more regular-season games (37) than any team in the NFL over the past three seasons, but haven’t been to the Super Bowl since winning it in February 2010.

Saints fans are all too familiar with the “Minneapolis Miracle,” the “No-call” and a second gut-wrenching loss in the playoffs to the Vikings last season in overtime. The hat trick of disappointment must make it seem like Groundhog Day for Who Dat Nation once the postseason begins.

Brees may have already retired if he had hoisted a second Lombardi Trophy anytime during the last three seasons. But coming so close only to come up short has provided the motivation to return.

If New Orleans wins Super Bowl LV, there’s no doubt in my mind Brees walks. But if they don’t, does he come back in 2021?

Set Up For Success

We mentioned earlier Payton and Brees share a unique bond. The veteran head coach and expert playcaller is also building that relationship with Hill. And considering Brees and Hill each signed two-year deals earlier this year, this team likes their QB tandem. Brees doesn’t mind it either.

Drew Brees just now on @PFT_Live: "If I'm back, and Taysom's along side me, call the plays that puts us in the best position to win. If that means Taysom Hill is taking 30 snaps a game, 25 snaps a game, so be it. I'm all for that."@ProFootballTalk #Saints #WhoDat

— Chris Simms (@CSimmsQB) January 31, 2020

The Saints are also on the verge of extending running back Alvin Kamara to a big contract. Keep in mind the organization is on pace to be more than $71 million over the cap next season as currently constituted (according to overthecap.com).

So, while this is clearly a “Super Bowl or Bust” season for the franchise, the team is set up for success. The Saints feature an incredibly talented roster and a creative front office.

The best-case scenario for Brees and New Orleans is a similar scenario to how Big Easy native Peyton Manning’s final season played out. After years of chasing that elusive second title and numerous disappointing postseason defeats, you finally cash in (though Brees’ arm is in better shape than Manning’s at the end). Or …

The Brady Route

But if the Saints lose again before the Super Bowl — or lose in the Super Bowl — does Brees pull a Brady (or Petyon to a certain extent — though neck injury question marks lingered) and play for another team? That seems unlikely. While both Brady and Manning had become synonymous with New England and Indianapolis, the relationship Brees has with New Orleans is next level.

We discussed the “Who retires first?” debate between Brady and Brees late last year and, even then (before Brady’s move to Tampa), Brees was a favorite (-140 vs +100). The pair face off in Week 1 Sunday. It will be the first game in NFL history in which both starting quarterbacks are over the age of 40.

Brees may be in the best position out of any of the quarterbacks mentioned. He’s as productive as ever and plays on a team with an elite roster. He bounced back from a thumb injury last season and looked splendid in his return.

But as he said, he’s on borrowed time. Plus, he has a cush broadcasting gig waiting for him that will likely pay him nearly the same as he’s making now (something Brady did not have).

Win or lose, 2020 will be Brees’ last one in a Saints uniform — and his last in the NFL.

The pick: Will Brees retire after the 2020 season? Yes (-150)