As the Dallas Cowboys gear up for the regular season, team owner Jerry Jones is in the midst of roster evaluations, aiming to construct a playoff-caliber squad. However, a glaring weakness at the backup quarterback position has emerged, prompting speculation about a potential blockbuster trade to bolster the depth chart behind starter Dak Prescott.
The Cowboys initially had high hopes for Joe Milton, acquired via a fifth-round pick trade in April. Milton was expected to solidify his role as the primary backup after the team praised his potential earlier this offseason. However, his uneven preseason performance—completing 26 of 47 passes for 265 yards and one touchdown—has raised doubts about his readiness. With only journeyman Will Grier as the other quarterback on the roster, Dallas is now exploring external options to ensure they have a reliable backup for their postseason aspirations.
Pro Football Talk’s Mike Florio has proposed a bold idea: the Cowboys should inquire with NFC East rivals, the New York Giants, about trading for their announced starter, Pro Bowl quarterback Russell Wilson. Florio’s suggestion hinges on the Giants’ emerging rookie, Jaxson Dart, who has turned heads with an impressive preseason, completing 26 of 35 passes for 291 yards and two touchdowns in just three games. Dart’s stellar play suggests he could soon claim the starting role, potentially making Wilson expendable. However, with the regular season approaching, the Giants are likely to give Wilson, a former Super Bowl champion, every opportunity to lead before transitioning to Dart. The Giants also have Jameis Winston, another potential trade candidate, adding intrigue to their quarterback situation.
Florio also floated other options for Dallas, including Kenny Pickett or Joe Flacco from the Cleveland Browns, or Sam Howell from the Minnesota Vikings. Each brings a different level of experience and upside, but none carry the same divisional drama as a potential Wilson trade. Acquiring a quarterback from a rival like the Giants would not only strengthen Dallas’ roster but also send shockwaves through the NFC East.
Another strategy for the Cowboys could be to wait until roster cuts, when teams trim down from 90 to 53 players, potentially making quality quarterbacks available. This approach would allow Dallas to assess the market without committing to a high-profile trade immediately.
With the regular season looming, the Cowboys face a critical decision. Will they stick with Milton and hope he develops, pursue a veteran like Wilson to challenge a division foe, or target a different signal-caller to secure their backup role? One thing is clear: Dallas is determined to leave no stone unturned in their quest for a Super Bowl run.