The Dallas Cowboys are staring down a pivotal offseason, where tough decisions are more than just a possibility-they're a necessity. After a season that revealed deep-seated issues on both sides of the ball, the Cowboys must now rethink their roster's identity.
With cap constraints and the aftermath of previous blockbuster deals, the front office finds itself in a tight spot. If Dallas is serious about reclaiming its contender status, sentimentality can't dictate their strategy.
Veterans who once embodied grit and stability might now be seen as financial burdens. Three pending free agents are at the heart of these crossroads.
The 2025 season was a rollercoaster for the Cowboys, ending in disappointment with a 7-9-1 record and missing the playoffs for the second year in a row. The season kicked off with a major trade, sending defensive star Micah Parsons to Green Bay for defensive tackle Kenny Clark and valuable draft picks. This move marked a defensive shift, but the transition was anything but smooth.
Dak Prescott delivered top-tier performances, but the team's inconsistencies elsewhere overshadowed his efforts. New addition George Pickens shone brightly, earning All-Pro honors and providing a true threat on the boundary.
Yet, the defense struggled, often losing momentum due to blown assignments and poor gap discipline. The Cowboys dropped four of their last five games, culminating in a deflating 34-17 loss to the Giants, a game that underscored the gap between expectations and reality.
What seemed like a roster reload felt more like a reset.
As the 2026 NFL Free Agency period approaches, the Cowboys face a defensive identity crisis. They need to overhaul the core of their defense.
After ranking among the league's worst in EPA per play in 2025, Dallas can't afford half-measures. Replacing the pass-rush production lost in the Parsons trade is the top priority, closely followed by finding a dynamic linebacker who can cover the field.
Safety depth is another pressing concern. Communication breakdowns and missed tackles plagued the secondary, highlighting the need for more agile coverage defenders.
On offense, the front office must carefully balance finances. With Pickens eligible for an extension and Javonte Williams as a key retention target, keeping Prescott's arsenal intact is crucial.
Every dollar spent on defense must be weighed against preserving offensive power.
This financial juggling act sets the stage for some tough goodbyes.
Donovan Wilson has long been a fan favorite for his physical style of play. However, roster building is about looking forward, not backward.
By March 2026, Wilson will be 31, and his aggressive play style, while effective, accelerates wear and tear. The Cowboys seem ready for a shift under defensive coordinator Christian Parker, focusing on range, coverage, and versatility-areas where younger players might excel.
Juanyeh Thomas, a restricted free agent, offers a more cost-effective and flexible option. Letting Wilson go could free up cap space for bolstering the pass rush or extending Pickens. It's a recognition that Dallas needs to get younger and faster in the secondary.
Running back decisions often reveal a team's competitive mindset. Miles Sanders' upcoming free agency comes at a tricky time for Dallas. Once a dynamic playmaker, Sanders is now approaching 29, with declining efficiency and explosiveness.
The Cowboys have clear priorities in the backfield. Javonte Williams is the top choice as a younger, more robust runner. Investing veteran money in Sanders would create redundancy, not balance.
The smarter move is to leverage the 2026 draft, known for its depth at running back. Pairing Williams with a cost-controlled rookie offers financial flexibility and versatility. While Sanders still has value on the open market, Dallas needs to prioritize youth over veteran continuity.
Jadeveon Clowney's role in 2025 was specific-bringing veteran pass-rush credibility after the Parsons trade. Clowney showed flashes of disruption and leadership, but the Cowboys' 2026 strategy is different.
At 33, Clowney can still set the edge and pressure the quarterback in bursts. However, he no longer fits as a foundational rusher. Dallas must focus on developing talents like Marshawn Kneeland and Sam Williams.
Financially, letting Clowney go is a straightforward path to cap relief. With Dallas projected near the cap limit, veteran edge contracts are a luxury.
Investing in younger, high-upside rushers or multiple rotational players better aligns with the team's rebuilding path. Clowney was a bridge, but extending that bridge delays necessary changes.
Allowing Donovan Wilson, Miles Sanders, and Jadeveon Clowney to leave would signal more than just financial adjustments. It would show that Dallas is ready for a structural overhaul rather than a superficial change.
The Cowboys are still anchored by elite offensive production and a high-performing franchise quarterback. But to sustain contention, they need defensive reinvention, cap discipline, and patience with development.
Saying goodbye to veterans is tough, especially when they're respected locker-room leaders. Yet, holding on to the past will only prolong mediocrity.