The Eagles’ lauded general manager isn’t a cap wizard — he’s just a man with a bold plan, crafted when he had nothing to lose.

“Let’s make really good bets. If a high percentage of them work out, we’re gonna be good. If they don’t, we’re not gonna be good, and I’m probably gonna be out in this crowd somewhere, watching this conference.”

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That was Howie Roseman about 14 months ago, speaking at the 2018 Wharton People Analytics Conference. This quote concludes the story of some free agent signing — I think it’s Alshon Jeffery — that owner Jeffery Lurie originally opposed, but changed his tune after taking a look at the various data that Roseman presented. This, Roseman thinks, is what makes the Eagles synergistic, different, and successful: their obsessive hunt for information, and their willingness to adjust course based off of it.

There’s no way to prove him wrong. As he speaks, the Eagles are fresh off of their first Super Bowl victory in history, yet only two years removed from the head-spinning 2015 season that cast Roseman into the timeout chair. With Howie at the helm, they sprinted back into contention with one of the priciest trade-ups in QB history, an unfettered approach to free agent acquisitions, and fearlessness in the face of fourth down.

Now, they 1) might 2) probably 3) do have the best roster in the league. But we’re getting ahead of ourselves.

It wasn’t that the Eagles just picked the right players and hired the right coaches — that happened, but it isn’t enough to explain the quantum leap. In 2015, the league was chugging along on its well-trodden path, wondering when the scales of the universe would finally drag the Patriots back down into the pack. Roseman had been exiled, yes — but from his stool in the corner, he could see the field a bit differently.

When he speaks of the year that Chip Kelly wrested control of the front office, Roseman discusses how an extrication from football allowed him to connect to other team-builders, other contract authors, other leaders. And when he came back, he wasn’t just refreshed or reinvigorated — he was rebuilt.

The Quarterback Builds The Window

“The history of trading up for one player, when you look at those trades, isn’t good for the team trading up and putting a lot of resources into it.”

That was Howie Roseman, about 4 years ago, speaking at the 2015 Sloan Sports Analytics Conference. He’s just begun his timeout, and over the next few weeks, he’ll watch as newly crowned personnel King Kelly moves on from LeSean McCoy, Trent Cole, Evan Mathis, and Jeremy Maclin for the sake of Byron Maxwell, Kiko Alonso, DeMarco Murray, and Ryan Mathews.

Oh, and he’ll ship Nick Foles off to the St. Louis Rams for Sam Bradford. That’s an important one.

When Kelly fell and Roseman regained control of the Eagles’ roster as a New Year’s present in 2016, national and local media wagged their heads. The wunderkind who never was had somehow wiggled his way back on top of a franchise he couldn’t hope to run, spouting off about the lessons learned during his 2015 hiatus. Head coaching candidates seemed lukewarm on Philadelphia — though, in hindsight, the term “head coaching candidate” seems lukewarm on Ben McAdoo — and the eventual hire of Doug Pederson was criticized as a uninspired remix of a glorious, forgotten age of Andy Reid football.

Roseman was anything but uninspired. The Eagles gutted Chip Kelly’s roster, retaining only productive holdovers and securing long-term talent. Fletcher Cox, Zach Ertz, Lane Johnson, and Malcolm Jenkins all got extensions; Brandon Brooks, Nigel Bradham, and Rodney McLeod were signed. Those seven names are important: each will restructure his contract at least once in the next three years.

These are Roseman deals — but as the man himself said in 2015, the massive trade-up for Carson Wentz went against his mode of thinking, against his models. The teams trading up were rarely favored in those mega-deals — but, crucially, the team that never traded up was even worse off. At the second overall pick, with scant draft capital over the next couple of seasons, and picking the wrong quarterback was a bad place to be — picking in the low teens once again, still without a starting quarterback, was even worse. Sure, if you swing, you might miss — but if you don’t, you’ll go down looking.

So Roseman got his rookie QB — and the rookie QB circumscribes the Winning Window, as prevailing NFL philosophy has discovered and flocked to in recent years, like frozen wanderers around a small fire. If we have this, we might be able to make it — we just might survive.

The rookie wage scale, installed in 2010, created the exploitable edge. Fixed so that teams didn’t have to pay rookies like the aforementioned and inglorious Sam Bradford a whopping $78M over six years before they saw him take a snap, the wage scale dictates rookie salary by pick slot. So Wentz — drafted second overall in 2016 — signed for a $26.7M contract over four years, and once pen touched paper, the clock started ticking.

With a starting QB on a rookie deal, the Eagles had room to make moves. The money that wasn’t going to Carson could go elsewhere. As The Ringer noted, the cap the Eagles saved on Carson Wentz’s 2018 deal, as opposed to Jimmy Garoppolo’s bank-breaking contract in San Francisco, was enough to pay for Jason Kelce, Michael Bennett, Lane Johnson, Alshon Jeffery, Zach Ertz, and 3 million Wendy’s Frosties. Or 750,000 Häagen-Dazs pints, if you prefer.

But the Winning Window doesn’t necessarily close when the QB enters his second deal, as Carson Wentz is about to do, following his market-setting extension. It’s hard to get to Super Bowls with rookie-deal QBs and even tougher to win them, due in large part to the fact that rookie-deal QBs are...well, young players. They aren’t perfect yet, and if you drafted one to start, it’s likely that your team isn’t that good either.

What’s anecdotally harder about the second-deal QB is acquiring and retaining surrounding talent, because you’re tighter up against the cap. Your star player suddenly quadruples in yearly value, and swallows up all that Häagen-Dazs money. All the while, he’s getting older, and while that may mean better, it could also mean more beat up — Eagle fans know all too much about that.

But Roseman was not content to let the cap close down on the Eagles, recent Super Bowl champions, 4-1 in the playoffs during his second tenure after going 0-2 in his first. The Eagles poured money into the 2016 season, doubling the league up on guaranteed money spent — and when they were up against the 2017 cap, Roseman kicked off Phase 2 of his reimagined philosophy.

Wrapping The Gauze Tighter

The restructuring began with Zach Ertz, four days before the 2017 league year opened — remember, Ertz had just signed a 5-year extension one year ago. At the time that Ertz crossed his T, the 5-year, $42.5M contract looked like this:

A relatively simple structure: base salary comprises the meat of the yearly paycheck, and can be either guaranteed or non-guaranteed conditionally. Signing bonus is money that immediately goes into the the player’s pocket, but the cap hit of the signing bonus can be spread across multiple seasons via a mechanism called proration. Ertz’s signing bonus was $8M, and it is prorated across five seasons (2016-2020, 2016 not depicted) at a rate of $1.6M/season.

Now, before the 2017 league year began, Howie, Zach, me, you, and your mama knew that Zach Ertz was going to play for the Philadelphia Eagles in 2017. To cut such a young, talented player was absurd from both a football and cap perspective. So, to create that 2017 cap room the Eagles needed, Roseman took as much of Ertz’s 2017 $4M base salary as he could and converted it into signing bonus.

This was good news for Zach Ertz. You have to wait to get base salary in the form of weekly game checks — signing bonus money goes directly into your pocket, guaranteed. But this was also good news for Roseman, as it meant he could now prorate that signing bonus money across the remaining seasons of the contract.

Zach Ertz’s 2017 restructure opened up $2.58M of cap space for the Eagles, which — when combined with a Sam Bradford trade and a Connor Barwin cut — got the Eagles safely in under the 2017 cap ceiling. And sure, it tacked $645k onto the cap of the next four seasons — but that was an easy long-term pill to swallow for the short-term relief.

Roseman quickly became infamous, in league circles and among Eagles fans, for his manipulation of the cap. Roseman would restructure another 2017 contract (McLeod) for further cap relief, and subsequently restructure five 2018 contracts (Jenkins, Cox, Johnson, Brooks, and Ertz) to create further cap room. Ertz’s was executed one day after the league year began, and opened up over $7M in cap space — which the Eagles almost immediately used to sign Haloti Ngata, Mike Wallace, and Richard Rodgers to 1-year deals.

Again, this is long-term risk for short-term reward — a kicking of the can down the road. The Eagles spent $1.8M of their cap room from 2019, 2020, and 2021 to sign 1-year role players like Ngata, Wallace, and Rodgers to fill out the depth of their roster. Instead of cycling in cheap draft picks with questionable NFL-readiness, they snagged still-cheap NFL veterans to take those snaps.

Things didn’t go according to plan with Wallace, Ngata, and Rodgers — each missed time with injury. But things didn’t go according to plan at all in 2018, with key franchise QB Carson Wentz missing time and playing through poor health.

When the new league year came around, the Eagles were once again up against the cap — at one point, projected to be $15M over the league ceiling. Rodney McLeod restructured; Nigel Bradham restructured; Lane Johnson restructured — Fletcher Cox had already restructured way back in October of 2018, in anticipation of generating 2019 cap relief. Why? Because the Eagles weren’t going to cut Cox before the 2019 season! So why not take that non-guaranteed base salary and turn it into guaranteed, immediate cash? Cash that Roseman could push even further down the line.

Still allegedly tight against the cap ceiling, the Eagles re-signed Brandon Graham, Ronald Darby — key veteran starters on a Super Bowl winning-roster. Most champions bleed talent — Roseman just wrapped the gauze tighter, keeping the Eagles’ cornerstones in place while increasing the pressure on the system.

Who made room for all of those free-agent retentions and additions? Zach Ertz, for the third year in a row, restructured his contract.

You’ll notice something new — namely, the years 2022 and 2023. There is no base salary for Zach Ertz in these seasons, his 10th and 11th in the league, 32 and 33 years old. That’s because he isn’t actually under contract in 2022 and 2023 — these years technically don’t exist.

In The Trash Compactor

I can’t tell you exactly when Roseman introduced the void years into his roster-building magic show — I think it was the Nick Foles contract originally signed in March 2017 — but now, they’re everywhere on Philadelphia’s roster. I count 11 contracts with significant void years currently on the Eagles’ roster — all of them either signed or restructured in the last 14 months.

The void year looks like a technicality and acts like a used car salesman — there’s no way this is real, and there’s no way it’s actually what it’s billed to be. These years serve as placeholders for proration, taking Roseman’s current methodology on cap extension and cranking it up to an 11. Roseman made his winning window — now he’s wedged himself inside its dwindling frame like Han and Leia in the trash compactor, trying to keep it open for just a second longer.

The more years over which you can prorate a signing bonus, the lower you can make the yearly cap hit of that prorated bonus. The CBA sets the current maximum at 5, and that length dictates Roseman’s use of voided years accordingly. He tagged 2 void years onto the end of Zach Ertz’s restructure in 2018 to prorate that restructured bonus over a total of 5 years (3 active, 2 void). When the Eagles re-signed Ronald Darby, it was on a 1-year deal with a $3.5M signing bonus...with 4 void years attached, putting the yearly cap hit at a mere $700k.

Sounds too easy, doesn’t it? Remember, void years are a used car salesman — or better yet, a payment plan. There are always hidden fees.

When the contract expires, it doesn’t matter how many void years are left — those dummy years vanish into thin air, and the player hits free agency. All of that prorated money accelerates back onto the year that the contract expired, and in effect, the only cap hit that is really lessened is the early year’s. Take Darby again: if he hits free agency in 2020, his four void years accelerate onto the 2020 cap, and the Eagles have to pay $2.8M of that $3.5M in 2020 to a player that isn’t on their roster.

Let’s look at Jason Kelce’s new contract as a clear example of the lies spun by voided years. Kelce’s was still slated to play on the team in 2019, but his restructure so significantly changed his deal, that it’s essentially a brand new contract. It looks like this:

The three void years are 2022, 2023, and 2024. They take on the final two years of the signing bonus ($7.57M divided over five years, 2019-2023) as well as the final three years of an option bonus, which is $7M divided over another five years, 2020-2024).

This contract looks so much more palatable than a contract without voided years. Kelce would still get the same amount of money, but it would gobble up the Eagles’ cap over its three-year duration. Roseman would never have signed this deal.

If Kelce plays out the course of his actual contract, which is in actuality a 3-year deal, then all of that prorated money floating in the limbo of the void years accelerates back onto the 2022 cap, when Kelce hits free agency. So, while the Eagles’ 2022-2024 cap numbers might look lower, in effect they’ll accelerate to become this:

Not nearly as pretty now, is it? Again, the Eagles would be paying $7.228M off the 2022 cap for a player not on their 2022 roster — that’s not good business.

And even a further note on the 2020 option, in navy blue: that option is early in the 2020 league year, and if the Eagles accept it, then they can prorate it across those 5 remaining seasons (2 active, 3 void) on the contract. If the Eagles deny it, all of that money accelerates onto the 2021 cap, as fully guaranteed salary.

This allows the Eagles to take a huge cap hit in 2021, to slightly lower the 2020 number and significantly lower the 2022 number. It’s unlikely that this happens at all — but if the Eagles are at a point where they know they won’t compete in 2021, it might be a year to eat up some money.

That 2021 year is important. When you calculate the effect of the voided deals on all of the Eagles’ cap projections over the next few years, 2021 is the year in which the difference is most drastic:

The Eagles cap numbers in 2020, 2021, and 2022 look smaller now (orange) — but when those contracts are voided and the prorated money accelerates back onto the cap (purple), the Eagles could find themselves paying nearly $10M to players not currently on the roster. That’s not bad for a team that isn’t competing — but for the Eagles, that $10M matters.

This paradigm is the key to understanding Roseman and the Eagles’ sudden rise: are you or are you not competing? Put another way: Do you have a quarterback who can take you to a Super Bowl? If not, then cap becomes useless and draft picks don’t do jack — you don’t have a shot anyway. That’s why you re-sign Sam Bradford and acquire Chase Daniel and trade the house for Carson Wentz, all in the same offseason. The quarterback builds the window.

But if you have him, then you’re competing, and you’re in the Winning Window — and just like that, draft picks matter and cap room is desperately needed. The switch flicks, and you’re denying team options instead of cutting players to prevent them from counting against you in the compensatory pick formula; you’re building a house of cards out of void years, with each addition increasing the trembling risk.

Is it worth it? Just ask Roseman: all decisions are bets. The Eagles bet on Wentz, got their franchise QB, and all of the subsequent decisions — the re-signings and the trades, the restructures and the voids — are double-downs. Wentz is the Window, and they’re all-in.

A Piper To Pay

The Patriots have been a competitive football team for the last 20 years — the Brady Window, we might call it, or perhaps the Brady Bay Window, or the Brady Skylight, or the Brady Greenhouse-Because-The-Entire-Doggone-House-Is-A-Window. Is that the model for the Eagles, and for the rest of the NFL? Is that how the pack catches up?

Almost certainly not. You can’t find another Belichick — if you could, it would have been done by now. The Patriots are an aberration, and even if you could distill their success into a formula, too much of it is dependent on one man.

For the rest of the league, it’s the understanding, acceptance, and maximization of the Winning Window that matters. If you have a shot, make it the best shot possible.

But with one end of the stick comes the other: with every Winning Window comes an other shoe just waiting to drop; a piper to pay; a flock of chickens come home to roost. Roseman saw an opportunity to get Carson Wentz, and he leapt at it — now he sees an opportunity to win another Super Bowl in 2019, and he’s after it again.

We don’t yet know what Carson Wentz’s mega-deal looks like, but we know enough about the ancillary contracts — Fletcher Cox, Brandon Graham, Brandon Brooks, Malik Jackson — that we can be certain a reset is coming. It might be in 2020, should Carson Wentz go down with another injury, and the Eagles need to restart the whole process; it might be 2021 or 2022, when the Eagles go dark in free agency and barely change the roster, suffocating under the prorated money come back from the grave; it might be even later, if Roseman elects to kick an even bigger can down the road.

Roseman is called a cap wizard in Philadelphia, and rightfully so — but not because he makes things disappear. He rather makes things jump, like a red sponge ball hopping from hand to hand to behind a child’s ear. It’s always somewhere, and he can choose just where it finally pops up.

The only thing the Eagles have that the rest of the league lacks is self-awareness — that which Roseman claims he found in 2015, he has crafted the organization after. They know they can win now, and they’re willing to do what it takes; later, they’ll know they can’t win, and they’ll amend their strategy accordingly. Having the humility to accept the day of reckoning when it arrives is key to the philosophy, but hey—that’s tomorrow’s problem.

For today, the Eagles are in line once again to compete for a Super Bowl.