
Cowboys Encouraged to Consider Trading Dak Prescott for Steelers’ T.J. Watt
The Dallas Cowboys are no strangers to controversial decisions, often drawing criticism for their moves. However, their recent acquisition of quarterback Joe Milton III was widely praised, adding both depth behind Dak Prescott and a potential long-term project. The buzz surrounding that trade has even led some to suggest Dallas go a step further — by dealing Prescott altogether.
One of the more bold ideas came from former NFL quarterback Kurt Benkert. He proposed a blockbuster deal: the Cowboys send Prescott and their first-round pick to the Pittsburgh Steelers in exchange for linebacker T.J. Watt and Pittsburgh’s first-round selection.
In Benkert’s words, “The Steelers get a QB and avoid a new contract, plus pick No. 12. Cowboys get pick No. 21 and Watt, and get to see what Milton can do. They’d have the best D-line in the NFL and a real shot in the NFC East.”
While imaginative, the scenario feels more fitting for a video game than reality. Beyond Prescott’s status as the team’s starting quarterback, his contract would present a massive obstacle. Trading him would leave the Cowboys with $148 million in dead cap money. On top of that, acquiring Watt — who’s seeking a new deal — would cost Dallas an estimated $160 million over four years.
The financial complications don’t end there. The Cowboys are also negotiating a major extension with star linebacker Micah Parsons, who may also command around $40 million per year. Pairing Parsons and Watt would certainly create a dominant defense, but it could severely limit Dallas’ salary cap flexibility. Plus, it would place pressure on Joe Milton to lead the offense.
In the end, while adding Milton was a smart and intriguing move, it’s unlikely to signal a shift away from Dak Prescott. For now, the Cowboys seem committed to their quarterback and their current path forward.