Cowboys urged to get ahead of looming Dak Prescott issue.

Dak Prescott’s contract situation with the Dallas Cowboys suggests the team should consider preemptive negotiation to avoid paying a lockup price in the near future. The Cowboys have already restructured Prescott’s deal twice, pushing substantial guarantees into the next two years, with about $76 million due next year and $86 million the following year. As those future sums loom, leverage wanes, making an earlier extension more favorable to cap space and long-term value.

NFL insider commentary argues the Cowboys should explore a new contract after this season, rather than waiting until the end of the current deal. The rationale is that delaying negotiations has historically cost the team leverage, and initiating a deal with two years left could allow folding some old money into a new, longer-term agreement while pushing more of the cap hit farther out. Prescott remains a top quarterback, coming off a productive 2025 season despite hamstring injury concerns, with strong passing totals and high completions, suggesting he remains market-leading.

Key considerations:
– Prescott’s health history and age (33 at season start) influence the risk-reward of a new deal.
– The Cowboys’ goal to balance immediate cap flexibility with securing a top-tier quarterback into the prime years.
– The strategic timing to avoid brinksmanship that previously eroded leverage.

Key Takeaways:
– The Cowboys are urged to proactively address Prescott’s contract to maintain leverage and cap control.
– A timely extension could consolidate current earnings into a longer, more team-friendly deal while extending his tenure as a top quarterback.