New York Giants quarterback Jameis Winston drops back to pass against the New York Jets. Rich Barnes-Imagn Images

3 backup QB options Cowboys should consider amid Joe Milton struggles

Originally posted on Dallas Cowboys on SI
By Randy Gurzi | Last updated Aug 18, 2025 8:10 AM ET

After watching Joe Milton struggle in his first two preseason starts, Dallas Cowboys head coach Brian Schottenheimer was preaching patience.

Schottenheimer said he doesn't need to name the team's backup quarterback yet and isn't ready to panic. While avoiding the panic button is a smart move, the Cowboys need someone to back up Dak Prescott whom they can trust.

While they have Will Grier on the roster, he hasn't taken a regular season snap since 2019 when he threw for 228 yards with zero touchdown passes and four interceptions. Instead of leaving their fate in his hands in an emergency situation, Dallas needs to explore one of the following options in free agency or through trade.

Kenny Pickett

A former first-round pick, Kenny Pickett spent two seasons as the starter for the Pittsburgh Steelers. He was traded to the Philadelphia Eagles in 2024, winning a Super Bowl as their backup.

This year, he's in a crowded quarterback room with the Cleveland Browns , where he's fallen behind Joe Flacco, Shedeur Sanders, and Dillon Gabriel. He could be waived, which would allow Dallas to put in a claim. They could also see if the Browns would be willing to take a seventh-round pick to ensure they landed him.

In three years, Pickett has 4,765 yards with 15 touchdown passes and 14 picks. He also has experience with George Pickens, and while they didn't always see eye-to-eye, Pickens had 1,140 yard s and five touchdowns the last year they worked together.

Carson Wentz

This one would be ironic since Carson Wentz was once seen as the savior for the Eagles. Still, he would make sense considering he has 94 career starts in the regular season and one in the playoffs. He's also the only one on this list who is currently a free agent.

Wentz never regained his form following a knee injury in 2017, but still has respectable numbers. He's completed 62.7 percent of his passes for 22,410 yards with 153 touchdown passes against 67 interceptions.

Jameis Winston

At first, this might seem like an impossible ask since it would involve the Cowboys making a trade with a rival, the New York Giants. However, the two teams did strike a deal in 2024, with Ne w York sending defensive tackle Jordan Phillips to Dallas.

The Cowboys should try and work out another trade with the Giants this year, targeting Jameis Winston. As it stands, Winston is third on the depth chart behind Russell Wilson and rookie Jaxson Dart. The Giants also have Tommy DeVito, meaning they could stand to part with Winston.

Of all the options out there, Winston would be the biggest addition. He could also be the biggest bust. Known for taking chances, the former No. 1 overall pick once threw for 5,109 yards but had 33 touchdown passes and 30 interceptions.

If anything, he would at least be fun to watch.