FRISCO – The Dallas Cowboys have made plenty of questionable moves in recent years, often leaving fans frustrated or amused. But their recent acquisition of quarterback Joe Milton III bucks that trend. The move adds depth behind starter Dak Prescott and gives the team a promising developmental player.
That smart decision sparked some wild speculation, including talk of trading Prescott himself. Former NFL quarterback Kurt Benkert joined in, suggesting the Cowboys send Prescott and their first-round pick to the Pittsburgh Steelers in exchange for T.J. Watt and the Steelers’ first-round pick.
Benkert posted on X:
“Steelers get a QB and avoid the contract + get pick #12. Cowboys get Pick #21 + Watt & get to see what Milton can do. They’d have the best D-line in the NFL and an actual shot in the NFC East.”
While the idea is bold, it’s more fantasy than reality — better suited for a Madden video game. Aside from Prescott’s heavy contract extension and public backing from the team, financially, this deal makes little sense for Dallas.
Moving Prescott would hit the Cowboys with $148 million in dead cap money. Meanwhile, acquiring Watt — who’s already hinting at wanting a big payday — could cost upwards of $160 million over four years. That’s a tough pill to swallow, especially with Dallas already trying to extend Micah Parsons, who may command a similar salary.
Yes, pairing Watt with Parsons would be a dream on defense, but the financial burden would severely limit the team’s flexibility — and force them to rely on an untested Milton to lead the offense.
Bottom line: Dallas made a smart, low-risk move in getting Milton. That’s where the story ends — not with a blockbuster trade for T.J. Watt.