Cowboys Arriving at 'Inflection Point' as Free Agency Nears

The Dallas Cowboys are one of the most intriguing teams this offseason and now, the franchise has reached the most pressurized moment in recent memory.

The Dallas Cowboys are quickly arriving at a defining point in the offseason as what transpires over the next couple of weeks could determine how the 2024 season pans out.

With the contract situation of Dak Prescott looming as the biggest domino to fall (or not to fall), much of what the Cowboys can and can't do rests on the outcome of that contract battle.

After coming up short again in the playoffs, the Cowboys, ideally, would be players in free agency and look to sign players that could put them over the top and give them a genuine push for a Super Bowl. 

But again, that is all predicated on Prescott's contract situation being sorted out. As such, ESPN thinks that Dallas is fast approaching a "damned if you do and damned if you don't" moment this offseason.

“The Cowboys are at a significant inflection point, with a good amount of cap resources to extend their stars -- QB Dak Prescott, WR CeeDee Lamb and LB Micah Parsons -- over the next year," ESPN writes. "But it will leave them with little room to sign external free agents. However, they do have to decide whether they should re-sign Tyron Smith -- who is unlikely to return -- Tony Pollard and Stephon Gilmore.”

Which way the Cowboys will go remains one of the greatest mysteries as we approach not only free agency but the start of the new league year (March 13).

If the Cowboys do harbor any serious intention to be Super Bowl hopefuls, then extending Dak or spreading the cap hit out over his remaining two seasons is what will give the franchise its best shot at being able to lure free agents to The Star. 

Additionally, the list of starters that are set to hit the free agent market is rather long. 

Tyler Biadasz, Stephon Gilmore, Tyron Smith, Jayron Kearse and Dorance Armstrong loom as more big decisions that Dallas has to make on whether it tries to retain them.

With Cowboys Nation fed up with the lack of postseason success, naturally the want for the franchise to genuinely go "all in" for that elusive Super Bowl is at an all-time high.

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But here we sit, with more questions than answers about the franchise's direction moving forward and there does appear to be an unwillingness to push all the chips into the middle of the table.

The events of the next couple of weeks have the potential to give Cowboys fans hope that the 2024 season might just be different than previous years, or that they could be set for a rather uncomfortable year ahead.

And it starts with what transpires with Prescott's contract situation.