LOS ANGELES -- For more than a decade, a three-ring royal blue binder labeled "Peyton Manning" sat on the office bookcase of Los Angeles Chargers general manager Tom Telesco.
Telesco grew so accustomed to seeing the binder on his shelf, he stopped seeing it at all.
Inside, Telesco had penned meticulous notes during his time as the Indianapolis Colts' director of player personnel. He had a front-row seat as Hall of Fame general manager Bill Polian orchestrated two contract extensions with Manning while also finding a way to field a Super Bowl-winning roster around his quarterback.
Telesco didn't discard the binder when he became a first-time general manager for the Chargers in 2013, but he didn't reference it often, either.
"I didn't have it really thinking, 'I'm going to need this with another job.' I just thought this is stuff I really need to drill down on," Telesco said, adding, "I didn't even think of pulling it out."
Until he did.
With Justin Herbert's continued ascent and the impending explosion of the quarterback market, it became all but certain this past fall that the Chargers would enter negotiations with the 2020 sixth overall pick on a long-term extension when he became eligible after the season.
"I pulled it out, started flipping through it," Telesco said. "And I'm like, thank God I have this."
The binder is a manual on how to navigate a quarterback contract extension that will consume a significant portion of the salary cap, while also building a team capable of a deep playoff or Super Bowl run.
"Some of it doesn't apply anymore," Telesco said, noting the change in the rookie pay scale implemented in 2011 to provide consistency among salaries and address excessive paydays for new pros. "But there's still some things in there that I've written down that I've learned that like, yeah, this definitely is going to apply."
Telesco and the Chargers are among several NFL front offices navigating how to retain young franchise quarterbacks and simultaneously build a playoff-caliber team around them. General managers, coaches and agents from around the league talked to ESPN about how to achieve it and the risks of doing it wrong.
After Philadelphia Eagles quarterback Jalen Hurts agreed to a five-year, $255 million extension that included $180 million guaranteed, and contentious negotiations between the Baltimore Ravens and Lamar Jackson ended with Jackson agreeing to a five-year, $260 million extension with $185 million guaranteed, Herbert and Cincinnati Bengals quarterback Joe Burrow are likely up next.
"When you're paying someone like we're going to pay this quarterback, he's making people better," Chargers coach Brandon Staley said of Herbert. "Not the other way around."
Determining whether a quarterback is capable of leading a team to a Super Bowl is the first hurdle. The next is ensuring he has enough talent surrounding him to get there.
"It's really a factor. It's a very real situation," Seattle Seahawks coach Pete Carroll said of reworking a roster around a significant quarterback extension. "The dynamics of the structure of your roster shifts.
"You really have to be creative and you really have to be fortunate in mixing the makeup of the roster to make it work."
TOM BRADY, WHO retired with seven Super Bowl rings, and Patrick Mahomes, with two titles over the past four seasons, haven't just skewed expectations for quarterback play on the field.
They've proved to be the outliers off it.
Each signed what some have labeled "team-friendly" contracts. Brady's deal equated to less money, and Mahomes agreed to a deal that spread a then-record-breaking extension over a long period, in an effort to help manage the salary cap.
So, how do you keep your quarterback financially content and build a team for long-term success?
"You've got to have a quarterback who understands the business and who's willing to ultimately have those conversations with his agent and us to find a deal that takes care of him, gives him the guarantees and the money he needs," Buffalo Bills general manager Brandon Beane said.
Brady, in 23 NFL seasons, didn't attract headlines with record-shattering contracts. He retired after the longest career in league history with $317 million in career earnings, according to Over the Cap, not including endorsement deals or the reported 10-year, $375 million contract he signed with Fox Sports to be a broadcaster in retirement.
Stars naturally gravitated toward playing with Brady, but it didn't hurt when courting wide receiver Randy Moss in 2007 and signing cornerback Darrelle Revis in 2014 that Brady's contract helped allow for their deals.
As he attempted to earn a seventh Super Bowl ring in Tampa, his first without the Patriots and coach Bill Belichick, Brady signed a two-year deal in 2020 with an average of $25 million per year guaranteed.
"Tom always took team-friendly deals to continue to surround himself with guys to help him win," Tennessee Titans general manager Ran Carthon said. "So it's one of those things that is based on the organization and that person in that role to help you figure out how you're going to continue to build a team."
Mahomes and Kansas City agreed to an eye-popping $503 million deal after he led the Chiefs to a Super Bowl in 2020. The extension spans 10 years -- an unusual contract length by NFL standards.
"Some people, they might say he is underpaid," Carthon said about Mahomes, who averages $45 million per season. "But you know, he has it figured out and it's cap-friendly and allows them to keep their guys and keep signing guys."
Mahomes' salary ranks seventh among the league's quarterbacks, but he said he wasn't concerned about money at Chiefs OTAs last week.
"Me, my agent and the team, always keep open communication and we try and do whatever is best for the team, but obviously I want to do the best for myself as well," Mahomes said. "But at the same time, I want to -- I've always said I worry about legacy and winning rings more than making money at this moment."
Chris Cabott, CEO of Equity Sports, represents Mahomes and several other NFL quarterbacks.
In Cabott's experience, multiple factors come into play when executing a quarterback extension, including whether there is stability in ownership and coaching, along with a nucleus of players who can help a team to a Super Bowl.
If those criteria aren't in place, a long-term extension -- like one that spans 10 seasons -- might not be best.
But if they are?
"You can have it all," Cabott said about the dynamic between a quarterback and team when negotiating an extension. "You can have the big contract and you can keep winning. It just takes a lot of work and it takes a lot of trust and takes a lot of communication.
"You can't win the game by yourself, so you have to be diligent about everything around you, but that should never be at the mercy of the compensation or the guarantees."
It wasn't long after Mahomes and the Chiefs struck their deal that Beane and quarterback Josh Allen played a round of golf together and the conversation turned to contracts.
"He and I talked a little bit about the pros and cons of that [Mahomes] deal and just some broad strokes of it," Beane said. "And we talked about Tom Brady and the championships he won, and so that's where it gets tough, because, yes, you want to be fairly compensated and it's not good for the team to get you on some deal that's not fair to you either because you're going to be unhappy and that doesn't work."
A year after Mahomes' extension and on the heels of an AFC championship appearance, Allen signed a six-year, $258 million contract.
"Josh was very adamant about -- 'I'll work with my people and yes I want to be recognized -- there's a respect thing -- but I also [want] to win and I want to be able to keep player X, player Y,'" Beane said. "Now, if I do that and then I don't back it up and I'm losing some of the guys that he thinks can help us win or we're going cheap now, we're probably going to have a problem."
THERE ARGUABLY IS no task more difficult in the NFL than finding a franchise quarterback.
"If you've got a quarterback, you're excited," Minnesota Vikings coach Kevin O'Connell said. "If you don't, you're excited to go find them."
That alone gives quarterbacks leverage when negotiating an extension, because when a team has a good quarterback, let alone a great one who has made the playoffs and had success, he will command record-breaking money.
It's known as the "pay-me-or-else mentality," one AFC executive said. It dares the organization to attempt the alternative and find a new quarterback, knowing there's zero guarantee how that will turn out.
Ask the Washington Commanders.
In 2018, Washington would not sign quarterback Kirk Cousins to an extension after he played two seasons on the franchise tag. Cousins reached free agency and signed a three-year, fully guaranteed $84 million deal with the Vikings, who have made two playoff appearances with him since.
The Commanders, meanwhile, have been in search of a quarterback ever since -- starting 12 players at the position in four seasons, all void of a winning record.
For the team, there is some pushback available: The most compelling way is to convince a quarterback he can achieve long-term success like Brady and Mahomes by taking a deal that, over time, will help him earn more by way of career success, longevity and endorsements.
"You got to know that there's some give-and-take that when you come across one of the great ones and you have to ultimately pay that high dollar number, you have to go along with the give-and-take of it," Carthon said. "There are teams that have figured it out."
But the question for many teams is getting the message to their quarterback, because agents oversee most contract negotiations, and their job is to get their client paid.
It could be perceived, with each deal richer than the last regardless of results, that some agents are mostly out for the money and are less concerned about the team's ability to field a great product around their player.
"The agent just wants bragging rights on getting the most money," one NFC executive said.
But Drew Rosenhaus, owner of Rosenhaus Sports Representation whose extensive client list boasts some of the NFL's top playmakers outside of the quarterback position, offered an alternative view.
"As an agent you try to balance it," Rosenhaus said. "You want to get the best deal for your client, but you're also interested in going to the right circumstance."
For the Mahomes deal, it was a giant puzzle that included not only putting a contract together but examining what each piece meant to the puzzle -- it was about being paid what he earned but also about setting the organization up for long-term success.
"For any quarterback at the end of the day, what your career is going to be measured by is 'Did you win? Did you win Super Bowls?' And if you can win multiple, you join a very, very exclusive club where obviously Tom Brady is at the top of the mountain" Cabott said.
Said Beane: "You got to think about your legacy, your career and the more money you take ... the less I can do to put weapons around you."
THE EAGLES SET the market with Hurts' deal. The Ravens followed, paying Jackson a little bit more. Now, the Chargers and Bengals are chasing an ever-increasing number.
For Herbert and Burrow, it's possible one is waiting for the other, knowing he will get a little more.
And many executives hope their quarterback is different.
"At least in our situation, I don't think I need to have that talk with our quarterback. I think he's fully aware, has really good self-awareness on how much money he is going to make, how it affects the team," Telesco said. "But like most agents will tell you, like, it's my job to figure out how to make sure that the player gets the value that he deserves and we build a team around him."
Herbert acknowledged seeing Hurts' and Jackson's new deals, but deferred to his representation when asked about the balance of getting paid and building a Super Bowl-caliber cast around him.
"That's the great thing about the people that I hired to work on my behalf is, I kind of leave it up to them because they're the experts and I don't know nearly enough about those negotiations, about those extensions," Herbert said. "... I have to be the best quarterback that I can be ... but obviously putting your input and making sure that everyone knows exactly what you would like from the situation."
Even with a recent influx of massive salaries, which included signing cornerback J.C. Jackson and trading for outside linebacker Khalil Mack last year, the Chargers have vowed all the moves have been made with the understanding their quarterback would be earning a significant, if not record-breaking, extension -- the type of deal they completed for outside linebacker Joey Bosa and safety Derwin James Jr. to pay them at the top of the market.
Across town in Los Angeles, the Rams have navigated several quarterback situations during the six-season tenure of coach Sean McVay, whose teams have reached the Super Bowl with a quarterback playing on a rookie deal -- Jared Goff, who earned $3 million in 2018 -- and with a veteran quarterback -- Matthew Stafford, who in 2021 was playing the final season of a five-year, $135 million extension that he signed with the Detroit Lions prior to his trade to L.A.
"Whether you have a quarterback on a rookie contract -- when we had Jared and the things that you were able to do, certainly it frees up finances, cash, cap, things like that that do make it a little bit easier to surround them with some of those great players," McVay said. "But then there's examples where you say you get a guy like a Matthew Stafford, you pay a player like Jared Goff because the importance of that position, and if that means you have to be disciplined in other areas you know, that's what you have to be able to do."
Telesco long maintained ahead of opening negotiations with Herbert that he does not subscribe to the theory that championship-caliber teams can only -- or most easily -- be constructed with quarterbacks on rookie contracts.
During the salary cap era, albeit ahead of the rookie wage scale, he watched it happen in Indianapolis, when Manning in 2004 signed the richest contract in NFL history -- a $99.2 million, seven-year deal that paid a league-record $14.17 million annually -- then two seasons later, led the Colts to a Super Bowl title.
"We've seen all sorts of teams do it and do it successfully," Telesco said. "The team I came from did it and did it successfully."
He might have spent years overlooking that binder, an artifact from when he was an understudy.
But he's certainly thankful to have it now.
Along with a quarterback who will be paid.