Insider reveals just how much waiting will cost Cowboys with Dak Prescott

When Dallas Cowboys owner Jerry Jones said the team would be going "all in" for the 2024 campaign, fans anticipated an offseason of blockbuster trades and splashy signings. The excitement never came. Instead, Dallas began to hemorrhage quality starters in free agency.

Regardless of what Jones said in his headline-generating press conferences, the Cowboys offseason was always going to be a quiet one. Dallas couldn't afford to make splashy free-agent signings with new contracts looming for quarterback Dak Prescott, wide receiver CeeDee Lamb, and linebacker Micah Parsons.

The problem? Dallas didn't sign any of their three star players to a long-term contract extension. The Cowboys have found themselves in a precarious situation and they have nobody to blame except themselves. The Cowboys have approached contracts in quite a baffling way.

In 2012, the New England Patriots signed tight end Rob Gronkowski to a six-year, $54 contract extension. He was just two years into his rookie contract. Bill Belichick, who was notorious for his conservative spending, locked down the future Hall of Fame tight end through the 2019 season, when he would be 30 years old. In comparison, Jones has kept his hands in his pockets for far too long.

The Cowboys don't seem to learn from their blunders. Just three years ago, Prescott backed Dallas into a corner. Dallas didn't sign Prescott early into his contract and, after two consecutive franchise tag designations, Prescott squeezed the team for a four-year, $160 million contract extension.

Cowboys may wind up paying Dak Prescott the richest deal in NFL history

Dallas appears to be repeating history once again. NFL agents and executives believe Prescott could command a contract in 2025 with a staggering average annual value of $60 million, according to Charles Robinson of Yahoo Sports.

“If money is his priority, he’ll get there,” one prominent agent said. “Especially if it gets to free agency and there’s more than one team involved.”

The figure may seem absurd at first glance, but it isn't too far off from the recent quarterback deals.

Signing Prescott last offseason or earlier this offseason would have saved Dallas a lot of salary cap space and, of course, money. Instead, Prescott increased their value with a first-team All-Pro campaign. The stellar performance, compounded with the rising market, made Prescott's value skyrocket.

Last year, the Baltimore Ravens signed quarterback Lamar Jackson for $52 million per year and the Los Angeles Chargers signed Justin Herbert for $52.5 million per year. This offseason, quarterbacks with fewer accolades have already surpassed those figures. The Jacksonville Jaguars signed quarterback Trevor Lawrence to a five-year deal with an average annual value of $55 million and the Detroit Lions signed quarterback Jared Goff to a four-year deal with an average annual value of $53 million.

Any quarterback who is more accomplished than Lawrence will certainly demand a higher figure than Lawrence's $55 million average annual value. Prescott certainly fits into that category.

Dallas could have inked their quarterback to a deal around Lawrence's value, but they opted to allow Prescott to enter the final year of his contract without an extension. If Prescott plays well, he'll need to be paid well. If he doesn't play well, the Cowboys season will be a disaster. Either way, Jerry Jones has set himself up to get hurt.

Dallas isn't new to contract blunders. The Cowboys signed Michael Gallup and Terrence Steele after major injuries, overpaid Ezekiel Elliott and Jaylon Smith, and shot themselves in the foot by waiting too long to sign Prescott. They already made the mistake of not extending Lamb last year, and now they're repeating that mistake by not signing Parsons in his first year of eligibility.