Cowboys Consider Trades to Upgrade Quarterback Depth Before Season

As the Dallas Cowboys approach the end of their 2025 preseason, critical roster decisions loom, including the potential trade of wide receiver Jalen Tolbert to bolster the defensive line depth. Backup quarterback Joe Milton has struggled significantly in the preseason, showing a low completion rate and multiple turnovers, prompting calls from analysts and insiders for the Cowboys to trade for a more reliable QB2, such as Jameis Winston from the Giants. Despite Milton being named the starter for the final preseason game, concerns remain about the lack of preseason reps for Dak Prescott, who has not played in a game setting since a hamstring injury last November, raising questions about the team's readiness for the regular season opener against the Philadelphia Eagles. The Cowboys face a tough NFC East division, with the Eagles recently acquiring wide receiver John Metchie, an upgrade that has sparked criticism from commentators like Skip Bayless, who urge Dallas to make significant roster improvements to remain competitive. The injury to Jonathan Mingo during the preseason, a key offensive player, further complicates the Cowboys' preparation, emphasizing the need for strategic moves ahead of the season. Overall, the Cowboys must address both quarterback reliability and overall roster strength to contend with the division's rising competition.