Reporter predicts if Cowboys will sign Dak Prescott, CeeDee Lamb before season

The unsettled futures of quarterback Dak Prescott and wide receiver CeeDee Lamb are casting massive shadows over the Dallas Cowboys, as both players remain on track to reach free agency following the upcoming season.

Cowboys beat reporter Jon Machota of The Athletic believes Prescott could stay unsigned through the campaign.

"In regards to Dak Prescott, an extension could get done before Week 1, but it also wouldn’t be surprising if they allowed him to play out the final year of his deal, see how the season goes and then decide to meet everything he’s looking for or decide to move on," Machota said for a piece published Monday. "The Cowboys generally don’t do deals during the season, so if Prescott doesn’t have a new deal by Sept. 8, it’s probably not happening this year."

It was reported ahead of the weekend by The Athletic's Jeff Howe that it didn't "appear" the Cowboys were close to getting something done with Prescott even though they "badly" want to lock him down via an extension. The 31-year-old finished second in Most Valuable Player Award voting for the 2023 regular season and could be looking to reset the market for players at the position via a deal worth up to $70M annually.

However, some have wondered if his 2-5 career playoff record has Cowboys owner and general manager Jerry Jones thinking twice about paying the signal-caller.

Dallas could try to replace Prescott by trading for a proven commodity such as Kirk Cousins of the Atlanta Falcons in March 2025.

As for Lamb, Jones raised plenty of eyebrows when he said last week he had "no urgency" to get an agreement done with the 25-year-old amid his holdout. Jones tried to walk that comment back on Sunday and insisted that Lamb is "missed" by the organization.

Per ESPN stats, Lamb led the NFL for the 2023 regular season with 135 receptions and 181 targets. He was second in the league with 1,749 receiving yards and third with 12 touchdown catches.

"It would be surprising to see the Cowboys not get a deal done (with Lamb) before the start of the season," Machota added. "They believe that even a contract holdout won’t prevent their star wide receiver from playing at a high level as soon as he returns. And they need Lamb at his best. Dallas' offense would be in significant trouble without its top playmaker."

As of Monday morning, DraftKings Sportsbook listed the Cowboys fourth among the betting favorites at +700 odds to represent the NFC in Super Bowl LIX. History shows championship-caliber teams can structure extensions in ways that allow them to hold onto multiple star players, but Jones appears to be in no hurry to make both Lamb and Prescott happy even though Dallas' regular-season opener is now less than a month away.