Ex-Packers QB proposes blockbuster Dak Prescott-T.J. Watt trade as Steelers star seeks contract extension

Former NFL quarterback Kurt Benkert, who played briefly with the Green Bay Packers in 2021, suggested a blockbuster trade involving Dak Prescott and T.J. Watt.

On Thursday, Benkert broke down on X how this hypothetical move would help both teams, as they'd address two key issues.

"TJ Watt for Dak Prescott & a first round pick swap — who says no Steelers get a QB and avoid the contract + get pick #12 Cowboys get Pick #21 + Watt & get to be see what Milton can do. They’d have the best D line in the NFL and would give them an actual chance in the NFC East."

"I actually think it gives upside to both teams situations mainly because they don’t have a chance at winning their division with their current circumstances roster build wise."

T.J. Watt is entering the final year of his four-year, $112,011,000 deal with the Pittsburgh Steelers. One would imagine a new contract would have been sealed by now, but the reality is different.

The Steelers are focused on Aaron Rodgers, who's been deciding on his future since the start of the 2025 free agency. Meanwhile, their top player's future is up in the air.

On the other end, the Dallas Cowboys made a bold move, trading for Joe Milton III with the New England Patriots. With Drake Maye poised to be their franchise quarterback, Milton wouldn't have many chances to shine in Foxborough.

Prescott is recovering from a season-ending hamstring injury, which could accelerate his decline. Having Milton on the roster is a solid backup plan for the NFC East.

Who would win a Dak Prescott-T.J. Watt trade?

This is an intriguing option for both teams, although unlikely at this point. The Dallas Cowboys have a young quarterback ready to take over from Dak Prescott, while the Steelers don't seem to be losing sleep over T.J. Watt's situation.

A hypothetical trade between these two squads would look like the Steelers won it at the beginning, since Prescott would connect with DK Metcalf and George Pickens, providing them an instant boost. However, over time, Watt and the Cowboys could emerge as the true winners of the deal.

Joe Milton III has a bright future, and Watt isn't slowing down. Pairing him up with Micah Parsons would be a nightmare for opponents. They should be more competitive than the Steelers in the long run, as long as Milton pans out just fine.