Aug 19, 2016; Arlington, TX, USA; Dallas Cowboys quarterback Dak Prescott (4) and quarterback Tony Romo (9) talk during the pregame warmups against the Miami Dolphins at AT&T Stadium. Mandatory Credit: Tim Heitman-Imagn Images Tim Heitman-Imagn Images

The scary Dallas Cowboys QB question Tony Romo knows all too well

Originally posted on Dallas Cowboys on SI
By Matthew Schmidt | Last updated Jul 2, 2025 12:30 PM ET

The Dallas Cowboys signed Dak Prescott to a massive four-year, $240 million contract extension heading into last season, making him the highest-paid player in NFL history in terms of average annual salary. But was it worth it?

Prescott's deal officially kicks in this season, one year after he saw his campaign end as a result of a brutal hamstring injury eight games into the season.

The 31-year-old is no stranger to injuries, having missed considerable time three of the last five years, which has certainly created a strain on the Cowboys.

Dallas went out and acquired Joe Milton via trade with the New England Patriots earlier this offseason to provide some insurance...or perhaps a successor?

Perhaps a broader question is whether or not Dallas would stick with Milton if he is forced to replace an injured Prescott in 2025, much like the Cowboys stuck with Prescott back in 2016 following a preseason injury to Tony Romo.

Remember: Romo was the sure-fire franchise quarterback at the time, but his last injury ultimately served as the final straw for Dallas. The Cowboys moved on from Romo, who then retired.

It was a jarring decision by Dallas that stunned the fan base, but everyone understood that it was the right move after seeing how well Prescott had been playing. Prescott was an unassuming fourth-round pick, but he established himself as the Cowboys' signal-caller moving forward.

Milton has not shown nearly enough to demonstrate he can actually be a viable starting option, so we should all probably pump the brakes for now. But it's important to remember that the same could be said for Prescott during his rookie campaign, and we saw how that worked out.

If Prescott gets injured again and Milton steps in and impresses, a conversation may need to be had. A very expensive one, at that.

This article first appeared on Dallas Cowboys on SI and was syndicated with permission.

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