No-brainer quarterback trade package is too good for Cowboys to refuse

Baltimore Ravens v Dallas Cowboys - NFL Preseason 2025
Baltimore Ravens v Dallas Cowboys - NFL Preseason 2025 | Sam Hodde/GettyImages

The Dallas Cowboys went into the preseason hoping Joe Milton would show enough progress to cement himself as the backup quarterback behind Dak Prescott. Whether it's nerves or simply slow-moving development, Milton has looked just as raw as he did coming out of Tennessee.

In two starts, Milton has completed 17 of 29 passes for 143 yards and one touchdown to two interceptions. His four turnover worthy plays are most among any quarterback who's dropped back at least 30 times and his 40.9 passing grade is the lowest of any QB, per PFF.

Brian Schottenheimer insists the Cowboys aren't "panicked" about Milton's play, but he cannot be trusted to run the offense if Prescott were to suffer an injury. Another trade unfortunately might be necessary, and the Giants have a no-brainer upgrade in Jameis Winston.

Cowboys should trade a 2026 sixth-round pick to the Giants for Jameis Winston

Intra-division trades are rare, but this makes sense for both parties.

The Giants have already named Russell Wilson their starter. He's looked good in the preseason, completing 10 of 14 passes for 136 yards. Assuming that carries over into the regular season and New York is competitive, he should start for most of the year.

What really makes Winston expendable, though, is the play of 2025 first-round pick Jaxson Dart. The former Ole Miss star ranks third among qualified QBs with a 74.3 percent completion rate on 39 dropbacks and owns an impressive 8.4 yards per attempt without throwing an interception.

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The Giants want Dart to learn the ropes rather than throw him to the wolves, but he's good enough right now to be the backup behind Wilson.

They signed Winston to a two-year, $8 million deal this offseason, but only $5.25 million of that is guaranteed. Trading Winston would save $1 million on the cap and result in a palatable $2 million in dead money.

Winston hasn’t lived up to being the No. 1 overall pick, but he's a competent backup who would at least keep the Cowboys competitive if Prescott missed time with another injury. He went 2–5 as a starter for the Browns last season, but had the offense clicking more than any other QB Cleveland trotted out.

Milton's play led to Dallas being out-snapped 79 to 47 against the Ravens' backups. The Cowboys would get their door blows off if Milton had to start regular season games for an extended period of time. They'd end up with a top five pick in next year's draft.

While a Prescott injury would likely sink the season anyway, trading for Winston would instill some hope that the team could compete every Sunday. That is all you can ask from a backup quarterback.

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