The Cowboys are staring down the most important offseason a marquee NFL franchise has had in some time. In the past few seasons, Dallas fielded what many considered a top-flight roster. Its recent drafts yielded quality players at a variety of positions, and a handful of aggressive trades provided reinforcements. It was hard to identify many weaknesses on the depth chart. But this spring, a staggering number of players are set to hit free agency, and the way the Cowboys have allocated their resources and handled certain negotiations could prevent them from retaining some of their best talent.

Any list of spring priorities begins with Dak Prescott. Negotiations with Prescott have dominated the post–Super Bowl news cycle, and it seems that the two sides still aren’t close to a long-term deal. It’s easy to cast blame on the Cowboys in this scenario; by waiting to extend Prescott, they’ve cost themselves money in the long run. But it takes two sides to get a deal done. Clarence Hill of the Fort Worth Star-Telegram reported that Prescott rejected a deal in September that would have paid him $33 million annually. That suggests the Cowboys have made a serious effort to keep Prescott, but there are a lot of outside factors to keep in mind. By that point, the Seahawks had made Russell Wilson the highest-paid player in football with an average annual value of $35 million. More importantly, the Rams had given Jared Goff a four-year extension with a $33.5 million AAV and a record $110 million in practical guarantees. Prescott’s representatives likely looked at the Goff deal, considered their client’s pending free agency, and thought, “Ya know what, we’re good.” The bet paid off in a big way. Prescott put together the best season of his career in 2019: He averaged 8.2 yards per attempt and threw for 4,902 yards with 30 touchdowns to lead an offense that ranked fifth in Football Outsiders’ passing DVOA.

If a team knows it wants to sign a player to an extension, waiting is a dangerous game. Delaying the Prescott deal gave the QB one final chance to pump up his value in a loaded offense with a promising first-year coordinator. It left time for the Seahawks to sign Wilson to a deal that dramatically shifted the quarterback market. And it brought Prescott to the brink of possibly using Patrick Mahomes’s impending mega-contract to gauge his worth. If Prescott’s desire last offseason was to become the highest-paid QB in the NFL, the Cowboys could have inked him to a deal north of $30 million per year. If that number was closer to the $35 million per season that Wilson received, that seems like a figure the Cowboys now wish they had forked over. A few million here or there isn’t going to make or break a team’s chances when it comes to a QB’s salary. On the other hand, having to use the franchise tag on Prescott for a combined total of about $70 million guaranteed in 2020 and 2021 before losing him would be devastating.

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There are other details that complicate matters. The Cowboys favor long contracts for homegrown players that keep their stars cost-controlled for five or six seasons. But the quarterback market shifts every couple of years. Prescott is only 26 and likely hopes to cash in one more time after QB price tags have soared higher. As a fourth-round draft pick in 2016, Prescott’s rookie contract made him arguably the biggest bargain in football up to this point. He’s earned the right to cash in—with this contract and beyond.

All the moving parts make it difficult to fully assign fault in this saga, but it’s safe to say Dallas missed a chance to clear this up somewhere along the way. Even if giving Prescott a record deal last summer might have been painful in the moment, losing a few million bucks per season would have hurt less than what’s on the horizon.

A potential stalemate and Prescott holdout is far from the Cowboys’ only issue this offseason. Amari Cooper, Byron Jones, Robert Quinn, Maliek Collins, Jason Witten, Randall Cobb, Blake Jarwin, Darian Thompson, Jeff Heath, and Michael Bennett are also set to become free agents. Some of those names are more important than others, but the collective takeaway stands out most: Dallas may have to replace up to eight starters going into the fall. The Cowboys are currently projected to have about $77 million in space, according to Over the Cap. That number could climb to nearly $100 million if the team chooses to convert a chunk of DeMarcus Lawrence’s $16.9 million base salary into a signing bonus and release or restructure the deal of defensive tackle Tyrone Crawford, who is set to count for $9.1 million against the 2020 cap. Yet even $100 million in space starts to dry up quickly when you consider how many holes the Cowboys have to fill.

The exclusive franchise tag would pay Prescott about $32 million in cash. Cooper is likely looking to top the five-year, $96.3 million extension that Michael Thomas got from the Saints last summer. Jones has been a bit lost in these conversations, but he’s a 27-year-old 2015 first-round pick who’s found a niche since settling into an outside corner role in the past two seasons. On the open market, it wouldn’t be surprising to see Jones land a deal comparable to the five-year, $75.3 million contract Xavien Howard got from Miami last May. The Cowboys could structure the Cooper and Jones deals to limit the total cap hit in 2020, but even then they’d still hand out about $67 million in new AAV during a single offseason. And that would be before addressing all of their other needs.

Someone is likely to be the odd man out among Prescott, Cooper, and Jones, and it’s almost certainly not going to be Prescott or Cooper. The quarterback’s relative negotiating power is obvious, and because Dallas traded a first-round pick to acquire Cooper in 2018, the 25-year-old receiver also has uncommon leverage. It’s hard to imagine a future in which both Prescott and Cooper aren’t Cowboys next season, but that won’t come cheap. And it’ll probably mean that a quality player like Jones will go elsewhere. Some may look at the Cowboys’ predicament this spring as a good thing. When you’ve hit on so many draft picks, it becomes virtually impossible to keep them all. But the franchise’s looming cap issues are about more than just the big contracts coming this offseason.

If the above scenario plays out, it would be misleading to say that Dallas is choosing Cooper over Jones. As contract talks stalled with some of their stars last year, the Cowboys handed out other deals that complicated matters. The difference between keeping or losing Jones doesn’t come down to a couple million more for Prescott. It’s what happens when you combine a Prescott deal with a six-year, $90 million extension for Ezekiel Elliott two years ahead of schedule and a five-year, $63.8 million contract for Jaylon Smith. The Cowboys were always going to extend Elliott after drafting him in the top five in 2016, and rewarding Smith after his incredible comeback from a career-threatening knee injury made some sense. But much like it’s wrong to frame the Prescott standoff as an inevitability, it’s wrong to treat the possibility of the Cowboys losing Jones as something that was always bound to happen given the circumstances.

Smoothly handling all of these simultaneous negotiations was never going to be easy for Dallas—and it was made even tougher after the franchise completed successful trades for Cooper and Quinn near the end of their deals. But it still seems like the Cowboys will field a weaker roster in 2020 than they could have. Dallas retained an off-ball linebacker and a star running back while failing to lock up an excellent quarterback and receiver duo for the long term, and the cumulative effect could mean that a reliable cornerback will walk away. The Cowboys have the resources to retain most of their core, but retooling this roster to match what it’s been in recent years will be a challenge. Dallas is turning over a new leaf under head coach Mike McCarthy, but it may be lamenting the chances it’s already lost.