Cowboy Roundup: Joe Milton’s Interest, Players in Need of Extensions

As the NFL offseason rolls on, the Dallas Cowboys continue to make headlines for their bold decisions and strategic moves, positioning themselves for a shot at the postseason in 2025. While much of the attention in Dallas is typically focused on the team’s offensive and defensive dynamics, there are a number of storylines that also warrant consideration, such as potential roster extensions and a surprise development surrounding a potential new quarterback.

In this Cowboy Roundup, we take a look at Joe Milton’s interest in joining the Cowboys, the players on the roster who may be in need of extensions, and the moves that could define the team’s future as it looks to return to Super Bowl contention. From contract negotiations to potential acquisitions, these storylines are key to understanding the Cowboys’ trajectory moving forward.

Joe Milton’s Interest in the Cowboys

The first major surprise to emerge from Cowboys circles involves Joe Milton, the quarterback from the University of Tennessee. Known for his strong arm and dynamic playmaking ability, Milton has caught the attention of several NFL teams as a potential prospect in the 2025 draft. However, recent whispers have suggested that the Dallas Cowboys may be particularly interested in the talented signal-caller, which raises some eyebrows and generates questions about the Cowboys’ plans for the future.

Milton, who has become a standout for the Volunteers, is an intriguing prospect with a rocket of an arm and an explosive presence in the pocket. At 6’5″ and with impressive athleticism, he has a combination of physical tools that many scouts see as intriguing, especially with his potential to develop into a starting NFL quarterback in the future. Given the Cowboys’ current roster situation, with Dak Prescott leading the offense, why would the Cowboys entertain the idea of drafting a quarterback in the first place?

Here are some possible reasons why Joe Milton could be a player of interest for the Cowboys:

1. Dak Prescott’s Contract Situation

Dak Prescott is locked into a significant contract that runs through the 2025 season, but at some point, the Cowboys will have to start thinking about the future. Prescott, while a talented quarterback, has had his ups and downs in recent seasons. The Cowboys front office may want to build an eventual successor, especially if they are unsure of Prescott’s long-term sustainability or if they feel that they could find a more cost-effective, high-potential option moving forward.

Milton, with his physical tools and raw potential, could fit that role as a developmental project behind Prescott. While he is unlikely to challenge Prescott for the starting role in the immediate future, the Cowboys could bring him in as a developmental backup with the hope of molding him into a future starter when Prescott’s contract becomes more burdensome, or if the team decides to move on from Prescott later.

2. Risk Mitigation

The Cowboys, after years of investing in Prescott, could also view Milton as a potential high-reward asset in case of injury. Having a talented backup quarterback who can step in and potentially thrive if called upon is always an appealing strategy, especially in a league where injuries are so common at the quarterback position.

Given Milton’s raw potential, Dallas could see value in drafting him later in the draft, letting him sit and learn behind Prescott for a couple of seasons before considering him as a viable backup or eventual starter.

3. Exploring Every Option at Quarterback

The Cowboys’ front office, led by general manager Jerry Jones, has often been criticized for not aggressively addressing the quarterback position in the past. In this cycle, if they are truly interested in Milton, it may reflect a change in philosophy — where they’re now open to exploring every option to build the future of the franchise, not just the present.

If Milton can develop into a starter with his cannon arm and ability to make plays under pressure, the Cowboys could be setting themselves up for the future without relying solely on the idea of Prescott continuing to carry the offense.

Players in Need of Extensions: Who’s Up for New Deals?

While the Cowboys are considering the potential future of the quarterback position, there are several key players on the current roster who are in need of contract extensions, which could have a major impact on the team’s future success. Here are the Cowboys players who could be in line for contract extensions or new deals in the coming months.

1. CeeDee Lamb – The Star Wide Receiver

CeeDee Lamb has quickly emerged as one of the top wide receivers in the NFL, and his contract situation is one of the most pressing issues for the Cowboys. Lamb, who was drafted in the first round of the 2020 NFL Draft, is entering the final year of his rookie deal in 2025.

Over the last few seasons, Lamb has shown tremendous growth, becoming Prescott’s go-to target and consistently putting up impressive numbers. With over 1,300 receiving yards and 9 touchdowns in 2024, he proved to be one of the most dangerous and reliable receivers in the league.

The Cowboys understand the importance of keeping Lamb as the centerpiece of their offense, especially in an era where star wide receivers are crucial to a team’s success. Lamb’s ability to separate from defenders, create explosive plays, and serve as a chain-mover makes him invaluable to the Cowboys’ offense. An extension for Lamb seems inevitable, but the question is how much it will cost the Cowboys.

A long-term deal for Lamb will be one of the biggest financial commitments the Cowboys make, but it’s clear that locking up Lamb for the future is a necessity if they are to remain a competitive offensive unit. Expect negotiations to heat up as the Cowboys aim to get this deal done ahead of the 2025 season.

2. Micah Parsons – The Defensive Superstar

Micah Parsons is another player who will likely be in line for a new contract soon. The former NFL Defensive Rookie of the Year and two-time All-Pro linebacker has cemented himself as one of the best defensive players in the entire league.

With his ability to rush the passer, cover ground sideline-to-sideline, and create havoc in every area of the defense, Parsons is a key building block of the Cowboys’ defense. His contract situation, however, is likely to get a bit tricky in the coming years. Parsons will be eligible for a massive extension after the 2025 season, and the Cowboys will have to decide how much they are willing to pay to keep him in Dallas long-term.

Given Parsons’ game-changing ability and his impact on the field, it’s almost certain that he will receive one of the most lucrative defensive contracts in NFL history. The Cowboys are likely to prioritize getting this extension finalized to ensure that their defensive centerpiece remains locked in for the long haul.

3. Trevon Diggs – The Ball-Hawking Cornerback

Another key piece of the Cowboys’ defense, Trevon Diggs, is also heading into the final years of his current deal. Diggs, known for his ability to generate turnovers and make game-changing plays, has become one of the league’s premier cornerbacks.

With a growing reputation for taking risks, Diggs’ ability to jump routes and create interceptions has made him a pivotal part of the Cowboys’ secondary. However, his aggressive style of play has also led to some inconsistent moments where he’s been burned by top-tier receivers. Still, his high ceiling and game-changing ability make him a valuable asset for the Cowboys.

Diggs will be due for a big payday soon, and if the Cowboys want to keep him as part of their defense, they will need to come to the table with a competitive offer. As with Parsons, locking down Diggs for the future is a top priority for the Cowboys.

4. Tony Pollard – The Versatile Running Back

Finally, Tony Pollard has emerged as the Cowboys’ lead back after the departure of Ezekiel Elliott. Pollard has proven himself to be a versatile and explosive playmaker, both as a rusher and a pass-catcher. After an impressive 2024 season, Pollard has solidified his place as one of the top running backs in the league.

Given the relatively short shelf life of running backs in the NFL, Pollard’s contract situation is one that needs to be addressed sooner rather than later. With the Cowboys likely to rely on Pollard as the centerpiece of their backfield for the next few seasons, they may need to extend him before he hits the open market.

Pollard’s versatility in the passing game adds another layer of importance to his role in Dallas’ offense. An extension for Pollard would ensure that the Cowboys maintain a consistent running game and keep a playmaking back on the field.

The Cowboys’ Financial Flexibility and Future Outlook

While the Cowboys face some challenging decisions when it comes to securing their core players for the future, they are in a relatively favorable financial position. With Prescott’s contract already locked in for the foreseeable future, and with the team able to make adjustments to the cap, the Cowboys should be able to make extensions work for key players like Lamb, Parsons, Diggs, and Pollard.

Ultimately, the Cowboys will need to balance their financial commitments while ensuring they maintain the necessary depth and talent across the roster. The upcoming contracts of these star players will shape the team’s future for years to come, and these decisions will likely play a significant role in determining whether the Cowboys can finally return to the Super Bowl.

The Path Forward for the Cowboys

As the Cowboys continue to navigate the offseason, the team’s interest in Joe Milton and the upcoming contract extensions for several key players are key storylines to follow. Whether it’s securing a future quarterback, locking down star players for the long term, or managing the team’s salary cap, the moves made in the coming months will define the Cowboys’ trajectory for years to come.

While the Cowboys’ roster looks strong on both sides of the ball, the ability to keep their core players in place will determine whether they can take the next step toward Super Bowl contention. With an eye on the future and the possibility of new stars emerging, the Cowboys are well-positioned to remain a top contender in the NFC.