As the Dallas Cowboys conclude their summer training camp, concerns are mounting over rookie quarterback Joe Milton III’s readiness to serve as the primary backup for Dak Prescott. Milton, who joined the team from the New England Patriots this spring, has struggled in preseason games, including a notably poor 2-for-8 outing against the Baltimore Ravens. These struggles have triggered rumors linking the Cowboys to Jameis Winston as a possible trade acquisition from the New York Giants, aiming to stabilize the quarterback depth chart.
Milton’s path to securing the backup role has been turbulent. Despite past success at Michigan and Tennessee, his performance in Dallas has been inconsistent, offering flashes of ability but not enough to firmly secure trust from coaches and the front office.
Jameis Winston Emerges as a Potential Solution to Backup Uncertainty
Milton’s challenges have reignited interest in adding a more experienced quarterback to support Prescott. Jameis Winston, formerly a starter for the New Orleans Saints, currently holds a modest two-year contract with the New York Giants. Insiders suggest that a trade for Winston could provide the Cowboys with a quarterback known for his strong arm, leadership, and game management skills—qualities that are currently lacking behind Prescott.
The Cowboys have long faced a dilemma between investing in a developmental signal-caller and acquiring a seasoned veteran who can immediately command respect and stability on the sidelines. With Cooper Rush no longer with the team and Prescott’s injury history a recurring concern, Dallas faces pressure to make a clear decision before the 53-man roster is finalized.
While negotiations for Winston would be complicated by roster limitations and contract considerations, the potential trade talks underscore the urgency in Dallas to shore up the backup quarterback position with proven experience.
Final Chance for Joe Milton to Secure His Role
The current depth chart firmly places Dak Prescott as the starter, with Joe Milton positioned as the likely immediate backup, though his spot is not guaranteed. Will Grier remains in competition but appears headed to the practice squad unless he can outperform Milton in the final preseason game. Milton’s upcoming appearance is critical, as it could cement his place or lead to the Cowboys pursuing a veteran alternative.
If the Cowboys decide to pursue Winston, Milton’s hopes for the backup role could evaporate quickly. Conversely, a strong performance in the finale may convince Dallas to continue developing Milton internally despite the risks. The team’s dilemma ultimately centers on which quarterback they trust more to lead the offense should Prescott be sidelined.
As the deadline for roster cuts approaches, the Cowboys’ quarterback situation remains volatile. Joe Milton’s window to prove himself is closing rapidly, and a surprising move like securing Jameis Winston could significantly reshape the team’s backup plans.