The Cowboys have a championship window. How long can they keep it open?

It's a bit surreal that we're even having this conversation about the Dallas Cowboys.

The Cowboys always foster playoff talk because of branding. They're one of the most successful organizations in football, and every unsuccessful season added to their 27-year Super Bowl drought makes the spotlight brighter.

The brutal reality, though, is that the Cowboys have rarely sustained success long enough to merit the idea of a championship window. They've made the postseason just nine times over the past 23 years, and 2022 saw them make consecutive playoff appearances for the first time since 2006-07. Whatever windows we've seen in Dallas recently have shut just as quickly as they've opened.

Whether you want to credit Mike McCarthy or the talent on his roster, that finally seems to be changing.

The Cowboys are eyeing a third consecutive playoff appearance in 2023, having won double-digit games each of the past two seasons. In that stretch, they've posted more regular-season wins than every other NFL team except Kansas City and Buffalo. With the NFC losing Tom Brady and Aaron Rodgers in the same offseason, the Cowboys look primed to continue that run of form.

So while the postseason success remains elusive, they are at least putting themselves in the conversation.

It begs the question of how much longer this roster can keep it that way. To that end, here's an attempt at an answer.

It starts with Dak 

This could all have a very simple answer depending on how the Cowboys handle their quarterback's contract. Dak Prescott's salary-cap number is incredibly manageable for 2023 after an offseason restructure, but that shift means he'll count roughly $60 million against next year's cap. The list of quarterbacks who can win big while accounting for roughly a quarter of their team's cap is not long, and Prescott isn't on it.

It doesn't leave Dallas much in the way of choices. The Cowboys could theoretically let Prescott play his contract out, eat the number and seek to draft a new quarterback in 2024. But given where they're likely to be drafting, not to mention what that would do to their chances of contending, that seems unlikely.

The more realistic scenario, as has been said all along, is that the Cowboys front office would be wise to get in front of an extension. Stability at the quarterback position goes a long way toward postseason success, and if re-signing Prescott early can push his cap figures down even a little bit, so much the better.

Deals left to make

I've written before about the financial obstacles ahead of the Cowboys in the form of contract extensions for CeeDee Lamb, Trevon Diggs and eventually Micah Parsons.

This team has never had issues re-signing its stars, so there's not much in the way of uncertainty there. If the Cowboys want to keep these guys around, they more than likely will. The question is mainly about the timeline for those decisions, and how much flexibility they can give themselves.

Lamb's fifth-year option has already been picked up, locking him in for at least two more seasons and giving the Cowboys more time to negotiate an extension. I'm going to go ahead and assume a year ahead of time that the front office will pick up Parsons' fifth-year option around this time next year. 

It's nice that they'll have the luxury of added time for these negotiations, but that shouldn't lessen the urgency. The sooner Lamb can be signed, the more years the Cowboys will have to spread out his cap hit, meaning the longer they'll have before his cost becomes a burden for them. The same can be said for Parsons when he's eligible to negotiate an extension starting next year. That's what makes Diggs the wild card. He was a second-round pick, so there is no option in his contract. He either needs an extension by March, or the Cowboys may be stuck carrying an $18 million cap charge on their books if they must franchise-tag him.

Bookkeeping isn't necessarily fun to read about, but these are the types of decisions that shape rosters. The timing and structures of these deals will have a major impact on what this team looks like over the next two or three years.

Reshaping the offensive line

It's tough to write about the Cowboys' offensive-line transition without feeling like a senior citizen.

Those who follow the Cowboys closely understand that the legendary lines of 2014 and 2016 are a distant memory. But we're approaching a day when even the cornerstones of those units will be gone. Tyron Smith, who joined the organization at the age of 20, is turning 33 this year and is playing out the last year of his contract. Zack Martin, a perennial All-Pro since being drafted in 2014, somehow is entering his 10th NFL season and has just two years left on his deal.

That's not to jump to conclusions. Martin is still arguably the best guard in football, and Smith can still play at a high level when healthy. It's not time to close the book on either career, but it is a brutal reminder that time is fleeting in pro football. As crucial as both players have been to the Cowboys' success, it's no longer too soon to consider the future. 

The Cowboys got ahead of that last year by spending a first-round pick on Tyler Smith, and that appears to have been a smart decision. Terence Steele looks like another timely find, though Steele is already in line for a new contract next spring. The same can be said for Tyler Biadasz, who earned his first Pro Bowl nod just in time for a contract season. Chalk it up to the joys of NFL roster construction.

[Is the answer to Cowboys' offensive-line uncertainty simpler than it seems?]

It's not to say the Cowboys need to go on another spending spree like they did in 2011-14, when they drafted an offensive lineman in the first round three times in four years. But this team does know the value of good line play. If the Cowboys want to maximize Prescott's value in the back end of his career, they'd be smart to stay a step ahead of that problem — a lesson they've hopefully learned from Tony Romo's career.

Nail the draft

Sounds simple, right? It is anything but.

The NFL Draft remains the best way to build and/or maintain a contender, because it's the only way to acquire premium talent without paying premium prices. Look no further than Lamb, Diggs and Parsons for evidence of how a great draft pick can affect your outlook.

For all the valid criticisms we can levy at them, the Cowboys have proven themselves as capable drafters. Roughly 85% of their two-deep for 2023 is comprised of guys they found during the draft process. Seven of their past 10 first-round picks have been voted as All-Pros at some point.

Past success isn't a guarantee for the future, though. Given the expenses that lay on the horizon, the Cowboys need to maintain their pipeline. Draft success is imperative to a team with an expensive quarterback — and even moreso if there are several other market-setting players on the books.

As the roster continues to turn in the next few years, draft success will be critical to remaining competitive.

Conclusion 

A fair amount of projection goes into this, and every year the NFL reminds us why predictions are a waste of time. Still, the foundation of a contending roster is in place for the time being, and the NFC is as wide open as it has ever been.

Consider the primary factors. The quarterback is costly and might need a new deal. The offensive line is aging into a new era. The secondary is littered with soon-to-be free agents. But led by Parsons and Lamb, there's a core of young talent that should ease a lot of concerns. It's just a matter of how costly that talent will become and how soon.

By my best guess, the Cowboys have three seasons to climb the proverbial mountain with this version of the roster in place. It's a short enough window to allow their longtime veterans to contribute while also keeping costs down on their coming extensions.

Good luck figuring out if that's good enough to reach the ultimate goal of a long-awaited sixth championship. At the very least, it's a welcome change to think the Cowboys have put themselves in the conversation for at least a few more years.

David Helman covers the Dallas Cowboys for FOX Sports. He previously spent nine seasons covering the Cowboys for the team’s official website. In 2018, he won a regional Emmy for his role in producing "Dak Prescott: A Family Reunion" about the quarterback’s time at Mississippi State. Follow him on Twitter at @davidhelman_.