The Dallas Cowboys conundrum

Once again, the Dallas Cowboys are at a crossroads.

The season-ending hamstring surgery for divisive quarterback Dak Prescott – two months after he signed a four-year, $240 million contract extension – while the Cowboys are 3-6, with a 2% chance of reaching the playoffs, amid a 29-year Super Bowl drought, brings to the fore an uncomfortable paradox between what this franchise signifies in theory and what it achieves in practice.

In mystique, aura and pageantry, the Dallas Cowboys are intergalactic. Sacrosanct, even. America’s Team, indeed. The NFL does not contain a more lucrative brand, nor a more powerful behemoth. Sports harbour no more valuable team, with Forbes valuing the Cowboys at $10.1 billion – more than the Green Bay Packers and Boston Red Sox combined.

The Cowboys also have world class physical resources. AT&T Stadium is perhaps the most awe-inspiring stadium on god’s green earth – a shimmering, 105,000-capacity monument to sporting opulence. The Star in Frisco, meanwhile, is an immaculate global headquarters without equal – a 91-acre campus, bold aspiration wrought in stainless steel. Between those two facilities, the Cowboys have almost $3 billion worth of cutting-edge amenities at their disposal – an unsurpassed foundation.

In the abstract, such advantages should drive the Cowboys to perennial success and semi-regular glory. However, in reality, their on-field performance consistently disappoints. Since the erection of those lavish buildings, Dallas has never won a single Super Bowl. It has not hoisted the Lombardi trophy since 1996, in fact – a bewildering fact at odds with the team’s illustrious image.

This, ultimately, is the Dallas Cowboys conundrum. They are excellent at everything, except winning on the field. Squaring that circle – solving that contradiction – has eluded multiple generations, and the attendant frustration gnaws at a conflicted fanbase.

The conundrum is Dolly Parton singing ‘We are the champions’ during the Cowboys’ Thanksgiving halftime show – a diet dupe of the Super Bowl extravaganza – while the team approaches a third decade without a ring. 

The conundrum is hordes of tourists traipsing through The Star on tours, paying a pretty penny, while players try to prepare for games.

The conundrum is those AT&T Stadium glass windows creating a mesmeric, sun-drenched backdrop for immense cinematography while blinding home receivers as routine catches go awry.

That which makes the Cowboys fascinating and compelling also makes them flawed and capricious. That which makes the Cowboys inspirational and prideful also makes them intransigent and preoccupied. That which makes the Cowboys majestic and lovable also makes them misguided and lost.

The Prescott injury crystallises these stark disparities once again. Indeed, Dak’s whole career – and, thus, his reputation – acts as a neat metaphor for a confusing Cowboys age. He has always been good, but never good enough, and that bittersweet realisation has become a staple of contemporary Cowboys fandom.

Remarkably, this was Prescott’s ninth season as the Cowboys’ quarterback. And while he has delivered five playoff berths, and holds an impressive overall regular season record of 76-46, he always seems to come up short when it matters most. In those playoff games, for instance, Prescott is 2-5, and he has never hauled Dallas beyond the Divisional round. His dignified failure has become metronomic, and Cowboys fans are stuck rooting for a likeable guy with infuriating flaws.

Prescott has become so predictable that his name is now associated with an entire tier of NFL quarterbacks – those who are generally very good, and who have elite abilities, but who ultimately fall below the elite echelon containing Patrick Mahomes, Lamar Jackson, Josh Allen, Brock Purdy and a few transient others. If somebody is described as a ‘Dak Prescott-type quarterback,’ you know exactly what that means and where they sit in the food chain. They are good, maybe even dynamic and exciting to watch, but they lack the X factor – the moxie, the nous, the killer instinct – to drag their team over the hump.

I really like Prescott and want him to succeed, but we now have almost a decade of data saying it will never happen. As Prescott goes, so go the Cowboys. And overall, they – the quarterback and his team – are just too nice. Nobody fears playing them, especially in the plush, climate-controlled comfort of AT&T Stadium. Rather, everyone relishes the chance to upset the Cowboys soap opera, which is remarkably easy to do.

As I wrote following last season’s 48-32 playoff humiliation by the Packers, ‘more than anything, the Cowboys are just too soft. I love the glitz and glamour. I respect the grandiose heritage and pristine image. But when the rubber meets the road, the Dallas Cowboys are never nasty. All too often, when the going gets tough, they roll over and have their bellies tickled. There is no substance to the sparkle, no concrete beneath the charisma. They are a castle built on sand, and the turrets get washed away every 12 months.’

The king of that compromised castle is, of course, Jerry Jones – the enigmatic owner, president, general manager, patriarch, emperor, ayatollah and commander-in-chief. Nobody – not even Prescott – embodies the Cowboys conundrum more than Jerry, whose bold dreams and bumbling colloquialisms have made him the focus of public attention for almost 40 years.

I will not re-litigate the polarising Jerry Jones debate here, because entire tomes have been dedicated to that arduous task. However, I mention Jerry simply because – like his beloved team – I still cannot pigeonhole the guy. He is at once a genius and a bottleneck, a visionary and a hindrance, a dreamer and a meddler, a showman and a curmudgeon, a bulwark and an egotist. To decipher Jerry is to decode the Cowboys – a thankless task immune to simple resolution.

Jones bought the Cowboys for $140 million in 1989 and has since presided over a 72-fold increase in his investment. There is a reason AT&T Stadium is known as Jerry World – because it is a physical manifestation of his peerless vision. Indeed, Jerry’s legendary business skills and unrivalled brand-building acumen ought to be taught on the national curriculum, and I have nothing but the utmost respect, appreciation and awe for what he has spawned. He transformed the Dallas Cowboys from a regional afterthought into a universal titan, and those contributions are immortal.

Jerry has also delivered three Super Bowl titles, of course. They were all in the 1990s, though, and with each passing year, their glorious afterglow struggles a little more to fuel modern rationale for the octogenarian Jones continuing as Cowboys general manager. Jerry is still responsible for all player personnel moves, and that frequently results in off-beat decisions such as the roundly-panned trade for Jonathan Mingo at the recent deadline. Analysts routinely mock Jerry’s roster-building, and the criticism is often valid.

Most specifically, the perpetual knock on Jerry Jones, GM, is that he lacks the patience and analytical acuity to construct Super Bowl-calibre teams. Grappling with a salary cap that dilutes the Cowboys’ financial fuel, Jerry is considered meddlesome, impulsive and, according to some, painfully out of touch with the latest evaluation practices. There are no checks or balances on Jerry’s autonomy, and his fickle whims dictate the Cowboys’ fate.

Yes, the Cowboys have been largely relevant for the vast majority of Jones’ premiership, and they even produced three straight 12-win seasons between 2021 and 2023 – a feat that many NFL teams can only envy. But such achievements ring hollow when, for generations, your own marketing machine has pushed a ‘championship or bust’ credo to anyone who would listen. You cannot set those standards in rhetoric, to attract passionate fans, then avoid accountability when said standards are not met in practice. To do so is incredibly disingenuous.

In this regard, there are myriad similarities between the Dallas Cowboys and New York Yankees – underwhelming modern teams encased in sacred, fabled franchises. It should come as no surprise, of course, that those two teams jointly own Legends Hospitality, a ‘food, beverage, merchandise and stadium operations corporation’ that yields $1.7 billion in yearly revenues. So long as people continue to buy jerseys and chicken buckets, championship rings are a ‘nice to have,’ rather than a necessity. And the Steinbrenner doctrine of winning – which inspired Jones as he formed his Cowboys blueprint – is now secondary to the mighty dollar.

Some say solving the Cowboys conundrum is as simple as compartmentalising Jerry’s remit; that the disparity between off-field excellence and on-field failure runs right through his spacious office. If Jerry would just surrender control of player personnel decisions, and focus on the brand he has so diligently crafted, the Cowboys could become a vertically integrated, fully functioning Death Star clicking on all cylinders – or so goes the prevailing critique. I tend to agree, but whether Jerry will ever swallow enough pride to make such a self-condemning move is the ultimate debate. Precedent says he will not.

When pressed on this, Jerry is quick to mention the theoretical advantages of his operating model – namely, its streamlined nature. Ostensibly, the Cowboys GM can conceive of a decision and execute it almost simultaneously, without having to jump through layers of interminable middle management – heads of this and presidents of that. In fairness, that simplicity is useful – if the person tasked with those GM duties is a football savant. And while Jerry’s hands-on involvement puts some NFL owners to shame, he is not a football savant. No amount of myth-making can change that.

All of which, naturally, brings us to the Cowboys’ miserable present and their uncertain future. Prescott will be back for kick-off in 2025. Mike McCarthy, the lame duck coach, almost certainly will not. A new figurehead will come in somewhere between Jerry, Stephen (his lieutenant son) and the field. The sliding scale of autonomy afforded to that incoming envoy will tell us a lot about how long the Cowboys’ champagne-scented malaise will persist.

To me, the perfect solution would be Bill Belichick – a disciplinarian to cure the culture, yes, but also a bottom-up conduit that could affect ethos change without altering the hierarchy too much. In other words, make Belichick the head coach and GM; let Stephen support him on player personnel operations; and bump Jerry to a Pontiff Emeritus position – the owner, marketing maverick and final arbiter, but with an epistemic distance to the experts running his football team.

Longtime Cowboys analyst Mike Fisher said it best this week when he called the Dallas Cowboys a ‘marketing company that just happens to play football on the side.’ And until they bifurcate those interests and give them equal, specialist attention, their chronic conundrum will continue. The Cowboys are at a crossroads, once again, and only Jerry can pick the correct way forward.


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