Mickey Loomis and Sean Payton are longtime friends.

They spent 16 years together with the Saints, where — as general manager and head coach — they won a Super Bowl and led the franchise to its most successful run in club history. Off the field, they golfed, shared dinners and traveled around the country for guys’ weekends.

Their relationship has endured the test of time. It’s about to be tested even more in the days ahead.

Once allies in one of the most successful rebuilding jobs in NFL history, they now find themselves on opposite sides of one of the most high-profile transactions the league has seen in years.

The Sean Payton coaching sweepstakes will directly affect the lives of scores of people and alter the trajectory of two of the league’s 32 franchises. It’s a major deal, and both Loomis and Payton fully understand its potential ramifications.

Payton and Loomis are both seeking a win-win outcome, even though they know it ultimately might be difficult, if not impossible, to attain.

“I know Mickey well,” Payton said this week on Colin Cowherd’s "The Herd" radio and TV show. “He’s got a job to do as a general manager with the Saints. He’ll get the right compensation. If it (negotiations) gets that far, he will arrive at it.”

Loomis clearly has done his homework here. Anyone who knows him knows his negotiating skills are second to none. Loomis is a skilled poker player away from his day job, and he loves nothing more than to match wits in a high-stakes negotiation. This Payton deal is right in his wheelhouse.

Other than a franchise quarterback, Loomis believes a head coach affects a team’s chances at success more than anyone in an organization and should be valued accordingly.

The market for a franchise quarterback was established this past offseason in blockbuster deals for Deshaun Watson and Russell Wilson. Wilson signed a five-year, $242 million contract that averages $48 million a year. Watson received a five-year, $230 million deal that pays him an average of $46 million a year.

The Cleveland Browns traded three first rounds picks and two mid-round picks to acquire Watson. The Denver Broncos traded two first-round picks, two second-round picks, a fifth-round pick and three players — including starting tight end Noah Fant — in exchange for Wilson.

What does that mean for Payton?

It’s complicated — and somewhat unprecedented.

Payton is believed to be asking for a contract that would make him one of the highest-paid coaches in the NFL. Two sources said he is seeking a four-year deal that would pay him between $20 million and $25 million. 

Loomis’ stance is if a team is willing to pay Payton a deal worth roughly half that of a franchise quarterback, then the draft pick compensation should be of equivalent value.

He’s seeking compensation similar to what the Oakland Raiders received from Tampa Bay in exchange for Jon Gruden in 2002, with two first-round draft picks being the starting point. If future first-round picks are part of the offer, then they would have to be supplemented by higher mid-round picks this season.

Whether Payton’s suitors agree with Loomis’ valuation remains to be seen. But in this negotiation, Loomis holds the cards. Payton is under contract with the Saints through the 2024 season, so the Saints own his rights. And any team that wishes to hire him as its next coach must compensate the Saints for his services.

If they are unwilling to match Loomis’ demands, he can nix the deal. The team would have to find a new coach, and Payton would have to return to his analyst role at Fox Sports for another year.

Meanwhile, Payton and his potential new team could call Loomis’ bluff and see whether he is willing to nix the deal and receive no compensation in a year in which the Saints lack a first-round pick because of a 2022 trade with the Philadelphia Eagles.

Loomis has told people in the Saints organization that he is comfortable with waiting a year for compensation, if it comes to that.

Payton has countered that the compensation would change “considerably … if nothing happens this year.”

Loomis contends otherwise. And historical precedent is on his side. In 1997, the New York Jets were forced to trade multiple draft picks to the New England Patriots — including a future first-rounder — to acquire the rights to head coach Bill Parcells.

“It’s complicated because I have such great respect for him,” Loomis said last week, referring to Payton. “He’s a close friend of mine. He’s a great coach. I want the best for him. I do. We do, collectively as an organization. He gave everything he could possibly give to the New Orleans Saints and took us to heights the organization, the team, never achieved before.

"So I absolutely want the best for him. But I also recognize that … his contract is a valuable asset to our club, and it’s our duty to maximize that.”

Payton began the interview process this week, meeting with the Houston Texans via Zoom on Monday and visiting with Denver Broncos officials in Los Angeles on Tuesday. He is scheduled to meet with Carolina Panthers owner David Tepper in New York on Friday. The Arizona Cardinals also have sought permission to interview Payton, although an interview has not been scheduled.

The interviews with the Texans and Broncos went well, according to sources. Payton was particularly impressed with the Broncos group, who he met with for several hours. He likes majority owner Rob Walton and the management team he has assembled in Denver. He’s also comfortable with the Houston brain trust and likes the draft capital, salary cap room and wide-open playing field he’d have to rebuild the Texans.

These interviews, though, go both ways. Payton is interviewing team officials as much as they are interviewing him.

“I think that’s critical,” Payton said, adding that he plans to ask “some difficult questions” of teams during the interview process.

There’s always the chance Payton goes nowhere. Teams could find the cost of signing him too exorbitant.

Likewise, Payton could not like the answers he hears to his questions and choose to sit out another year and see whether a better market develops for his services in 2024.

Sources said he was leaning toward staying at Fox for another year before the interview process began, but things can change when you start meeting with people face to face.

Regardless, the Payton sweepstakes promises to be great theater with two good friends staring each other down on the opposite side of a poker table.

We will soon find out who has the winning hand.

Email Jeff Duncan at JDuncan@theadvocate.com or follow him on Twitter at @JeffDuncan_