The Dallas Cowboys entered the preseason with high hopes for Joe Milton, expecting the young quarterback to solidify his role as Dak Prescott’s backup. However, Milton’s performances have been underwhelming, to put it mildly. His raw talent, evident from his days at Tennessee, hasn’t translated to the NFL stage. In two starts, Milton completed just 17 of 29 passes for 143 yards, with one touchdown overshadowed by two interceptions. According to PFF, his four turnover-worthy plays lead all quarterbacks with at least 30 dropbacks, and his dismal 40.9 passing grade is the lowest among his peers. The Cowboys’ offense has sputtered under his command, getting out-snapped 79 to 47 against Baltimore’s backups in a recent preseason game. If Milton were thrust into regular-season action, Dallas might be staring down a top-five draft pick in 2026.
Despite offensive coordinator Brian Schottenheimer’s insistence that the team isn’t “panicked,” the reality is stark: Milton isn’t ready to steer the ship if Prescott goes down. The Cowboys need a reliable backup, and a golden opportunity has presented itself in the form of a potential trade with the New York Giants for Jameis Winston—a move that could be a steal for Jerry Jones at the cost of a mere 2026 sixth-round pick.
Intra-division trades are rare, but this one makes sense for both teams. The Giants have already named Russell Wilson as their starting quarterback, and he’s looked sharp in the preseason, completing 10 of 14 passes for 136 yards. If Wilson maintains that form, he’ll hold the starting job all season, assuming New York stays competitive. Meanwhile, the Giants’ 2025 first-round pick, Jaxson Dart, has turned heads with a 74.3 percent completion rate on 39 dropbacks and an impressive 8.4 yards per attempt without a single interception. Dart’s readiness to serve as Wilson’s backup makes Winston expendable.
Winston, signed to a two-year, $8 million deal with only $5.25 million guaranteed, is a low-risk acquisition. Trading him would save the Giants $1 million in cap space while incurring just $2 million in dead money—a small price for a team confident in its quarterback depth. For Dallas, Winston represents a massive upgrade over Milton. The former No. 1 overall pick may not have lived up to his draft hype, but he’s proven himself as a capable backup. Last season, he went 2–5 as a starter for the Cleveland Browns, yet his ability to keep the offense humming outshone any other quarterback Cleveland fielded.
Dak Prescott’s injury history looms large over the Cowboys’ season. While a prolonged absence would likely derail their playoff hopes, Winston’s presence could keep Dallas in the fight week after week. His experience and ability to manage games would provide a level of stability Milton simply can’t offer. In a worst-case scenario, Winston could prevent the kind of catastrophic collapse that might result from Milton starting multiple games.
For a 2026 sixth-round pick, Jerry Jones has a chance to secure a seasoned quarterback who can keep the Cowboys competitive in a pinch. Winston’s arm talent and veteran savvy could be the difference between a respectable season and a complete disaster if Prescott misses time. The Giants, with Wilson entrenched and Dart waiting in the wings, have little reason to hold onto Winston. This trade is a rare win-win, and for Dallas, it’s a chance to bolster their roster without breaking the bank.