While NFL teams shouldn't exactly focus on "winning" the offseason, it's never smart to actively lose it. Unfortunately for their fans, the Dallas Cowboys have mishandled virtually every step of the 2024 offseason. Thursday's extension for Jacksonville Jaguars quarterback Trevor Lawrence served as the stamp on Dallas' failing report card.

According to ESPN's Adam Schefter, Lawrence has agreed to a five-year extension worth $275 million. That puts Lawrence on par with Joe Burrow in terms of annual contract value and presents a massive problem for the Cowboys.

We had already given Dallas a failing grade for their offseason before the Lawrence deal. Now, the Cowboys' missteps somehow look even worse. The Cowboys failed to get an early extension done with Dak Prescott, and that's going to cost them in both the short and the long term.

Here, you'll find a look at exactly how the Cowboys mismanaged Prescott's situation, the likely repercussions and what's next for what has become arguably the league's most mediocre franchise.

Dallas Had Its Chance to Sign Prescott Early in the Offseason

Dallas' 2024 failure can mostly be traced back to its inability to extend Prescott at the start of the offseason. We'll dive further into that shortly, but none of that changes the reality that the Cowboys could have moved quickly to get a deal done.

Prescott even told reporters in mid-April that he didn't "necessarily" want to be the league's highest-paid quarterback. At the time, that might have meant a deal similar to those of Lamar Jalen Hurts, Lamar Jackson and Trevor Lawrence—who are set to earn $51 million, $52 million and $52.5 million annually, respectively.

That was before Jared Goff signed a deal worth $53 million annually, blurring the financial lines between above-average quarterbacks and elite ones.

Whether Prescott is truly an elite quarterback or not, he can expect to be paid like one. Lawrence's deal pretty much seals that reality because the 24-year-old had far less leverage than Prescott does and still got paid top-of-the-market value.

"We'd like to see more leaves fall," franchise owner Jerry Jones said in April, per Patrik Walker of the team's official website.

It's hard to know exactly what Jones was waiting to see, but waiting has only driven up his quarterback's price point.

The Cowboys Have Lost All Leverage with Prescott

Jacksonville should have been far more interested in waiting to see more from its quarterback than Dallas has. Lawrence was a Pro Bowler in 2022, but that campaign was sandwiched between two underwhelming seasons. Prescott is a three-time Pro Bowler who has helped deliver five playoff berths and led the league in passing touchdowns last season.

Lawrence had two years remaining on his rookie deal, while Prescott is scheduled to be a free agent in 2025. Keeping him via the franchise tag isn't an option for Dallas because Prescott's contract includes a no-tag and no-trade clause.

Dallas' only real leverage play was to try convincing Prescott that he wouldn't get the deal he is looking for on the open market and agree to terms that benefited the Cowboys.

Good luck with that now. In addition to Goff and Lawrence both getting their paydays, Kirk Cousins got a deal worth $45 million annually on the open market, despite being 35 years old and coming off a torn Achilles.

Prescott is five years younger and is coming off the best statistical season of his career.

A team-friendly deal simply isn't going to happen. With Lawrence getting $55 million annually and $200 million guaranteed, Prescott can now demand Goff's deal ($170 million guaranteed for four years) and act as if he's doing Dallas a favor with a straight face.

Or, he can simply college his $55.5 million in 2024 earnings and roll the dice in free agency. With both Tua Tagovailoa and Jordan Love still awaiting extension—and Brock Purdy extension-eligible next offseason— the market will only continue going up.

Keeping Dallas' Core Together May Be Impossible

Prescott isn't the only player waiting for an extension from the Cowboys. Star receiver CeeDee Lamb is entering the final year of his rookie deal, while pass-rusher Micah Parsons became extension-eligible this offseason.

However, it was always important for Dallas to extend its quarterback first. Parsons has two more years on his contract, and Lamb can be given the franchise tag in 2025. Of course, neither player will be cheaper to sign in the future than now.

The Cowboys have already watched Amon-Ra St. Brown, A.J. Brown and Justin Jefferson take turns resetting the receiver market this offseason. Jefferson now leads all NFL receivers—and all non-quarterbacks—with a contract worth $35 million per year. That's now the bar for receivers like Lamb and Ja'Marr Chase.

Parsons isn't in a rush to sign his second contract but also knows that waiting could result in a deal worth far more than Jefferson's.

"This market is going to just jump up and the cap goes up again next year," Parsons said, per Clarence E. Hill Jr. of the Fort Worth Star-Telegram. "They're talking about these contracts might for a high caliber player might be up to $40 million by then."

Even if the Cowboys can work out an agreement with Prescott, paying him, Lamb and Parsons a combined $120-130 million annually isn't exactly feasible. Unfortunately, jumping the market with either Lamb or Parsons might not sit well with Prescott as he waits for his turn at the table.

2024 Has Become a Super Bowl or Bust Season

Dallas' baffling reluctance to get core players under contract sits in stark contrast to what the Philadelphia Eagles have done. Philly locked up Hurts when it first got the chance and extended players like Brown, DeVonta Smith and Jordan Mailata this offseason.

The Eagles' core is in place for the foreseeable future, while Dallas' could split as early as next offseason. This makes 2024 perhaps the Cowboys' last real shot at pushing for a Super Bowl before a major overhaul ensures.

Adding to the make-or-break nature of the coming season is that head coach Mike McCarthy is on the hot seat. Jones may insist that McCarthy isn't playing for his job, but McCarthy isn't under contract beyond this season.

If the Cowboys lose early in the playoffs in embarrassing fashion—as they did in January—Jones will almost certainly look to make a change. That is, of course, assuming that Jones actually wants to win a Super Bowl and isn't just happy with his team being relevant.

"I like that fact that he's hanging around the rim, and I like what the team has done to hang around the rim," Jones said in January, per Michael Gehlken of the Dallas Morning News.

That's one way to put it. Dallas has won 36 games over the past three seasons and does remain interesting. Yet, it hasn't advanced past the divisional round since 1995. If the Cowboys don't make their run this season, they could be trying to make it with a new head coach and without several top players in 2025.

Except the 2024 Outlook Isn't Great Either

Let's circle back to Dallas' inability to extend Prescott early in the offseason. The Cowboys have just $10.2 million in cap space after Michael Gallup's post-June 1 cut hit the books. Theoretically, they could save quite a bit more by extending Prescott now.

According to ESPN's Todd Archer, a simple restructuring of Prescott's contract could save roughly $18 million. Dallas could generate that space by restructuring Prescott's deal as part of an extension. That might give the team enough space to negotiate with Lamb and/or Parsons, though Prescott would have to play along.

What the Cowboys can not do is go back to the start of the offseason and generate cap space ahead of free agency. They lost key contributors like Tyron Smith, Tyler Biadasz, Tony Pollard, Dorance Armstrong, Dante Fowler Jr. and Johnathan Hankins. Dallas signed Eric Kendricks, Ezekiel Elliott and Royce Freeman in free agency, and that's it.

The Cowboys will now depend heavily on rookie offensive linemen Tyler Guyton and Cooper Beebe, who will both be asked to play new positions in the NFL. The alternatives along the offensive line aren't great—they include moving Tyler Smith to left tackle and creating a hole at guard—and Dallas is eyeing several other problem areas.

Elliott, Freeman and Rico Dowdle don't exactly form a high-upside backfield. The Cowboys still lack reliable receiver depth behind Lamb, and Kendrick alone won't instantly fix a run defense that ranked 16th in the league last season.

Had the Cowboys extended Prescott early—possibly extending Lamb and Parsons subsequently—they might have been players in free agency. That window has closed, and there's no denying the fact that Dallas' roster is markedly worse than it was a year ago. That's not ideal in a make-or-break season.

Meanwhile, teams like Philadelphia, the Green Bay Packers and the Detroit Lions were able to improve through both free agency and the draft. All of this means that the Cowboys could be headed for disappointment in 2024 and a rebuild in 2025 and beyond.

That's the simple reality for a franchise that stumbled with Prescott's situation and has failed virtually every step of the way since.

*Cap and contract information via Spotrac.