Cowboys free agency: Stealing a free agent from every NFC East team in 2025

Imagine if the Cowboys signed a free agent from every NFC East team.

There is no better feeling in the NFL than seeing your football team improve, while the others in your division take a step back during the off season. The Cowboys have been on the losing end of that stick for the last few years, but could things finally change in 2025?

It was announced on Wednesday that the salary cap would see a large jump in 2025 from where it was in 2024, an increase even more than teams expected this offseason. With the added cap space and some likely big restructures (Dak Prescott and CeeDee Lamb), and a potential Micah Parsons extension coming, the Dallas Cowboys could have north of $80M to spend this offseason.

With that money, the Cowboys would have resources to fill roster holes that are littered throughout their team. As of today, the Cowboys need starting caliber players at wide receiver, running back, cornerback, defensive tackle, defensive end, and linebacker and could use upgrades along the offensive line, safety, and tight end positions. Today we will take a look at free agents from the Washington Commanders, Philadelphia Eagles, and New York Giants and see what players they could realistically go after from their division rivals.

Washington Commanders

Jeremy Chinn, SAF

Projected Contract: 3 yrs — $7.5m avg/yr

Photo by Cooper Neill/Getty Images

The Cowboys currently have their two starting safeties from the 2024 season returning in 2025, but with some recent slippage in play, safety is a position they could upgrade this offseason. Jeremy Chinn is a versatile safety that can do a lot of the interchanging Matt Eberflus likes in his safeties.

Chinn, just 26 years old is young, relatively affordable, and is a quality player against the run and the pass on the backend. The Cowboys could save just over $5M in releasing safety Donovan Wilson and could use the savings to bring in Chinn, who has been a much better players recently.

Philadelphia Eagles

Milton Williams, iDL

Projected Contract: 3 yrs — $21m avg/yr

Photo by Gregory Shamus/Getty Images

This is where things get a little interesting. The Cowboys have a decision to make on their own player, Osa Odighizuwa, and they may be better off electing to move on from their former third-round selection and going with Milton Williams instead.

Pro Football Focus projects Odighizuwa’s contract to be four years, $21.25m avg/year while Milton Williams projected contract is three years, $21m avg/year. Odighizuwa and Williams are very similar players at the 3-technique position with Williams receiving a 70.1 overall grade from PFF and Odighzuwa receiving a 68.1 overall grade. Both Odighzuwa and Williams are very good pass rushers, who can struggle a bit to defend the run, but with Williams being a bit younger, projected to be a bit cheaper, and proving to be a slight upgrade over the last few years, this is the splash the Cowboys could make to give them a slight edge over the reigning Super Bowl champions.

Milton Williams went to high school at Crawley High School in Crawley, Texas and has some ties to the area, making his fit in Dallas one a bit more realistic than other destinations around the league.

New York Giants

Isaiah Simmons, LB

Projected Contract: N/A

Photo by Sarah Stier/Getty Images

This is the type of player the Cowboys normally like to go after in free agency. The former eighth-overall pick in the 2020 NFL draft has had a disappointing career so far, but this low-risk, high-reward signing makes all the sense in the world for the Cowboys.

Simmons will likely not be highly touted this offseason and Dallas has a big need at linebacker with Eric Kendricks a free agent and DeMarvion Overshown likely to miss most if not all of the 2025 season. The Cowboys love signing former first-round picks to one-year deals in free agency and seeing if they can get something out of them. Simmons will likely be cheap and will allow the Cowboys to fill a position of need heading into the draft.