As we approach the start of NFL training camps, the group of people who have faith in the Dallas Cowboys having a successful 2025 season seems to dwindle exponentially. Every day, someone jumps ship or takes a shot.
And that’s understandable. The Cowboys seemed to be building toward something with consecutive 12-5 seasons in 2022 and 2023 before going fully in the tank in 2024 with a 7-10 record — and they’ve done little to show they’ll be much better this season.
Bleacher Report’s Alex Kay put the Cowboys at the top of his list of NFL teams who could be aggressive sellers at this year’s trade deadline — a.k.a. teams who will be out of playoff contention by the trade deadline.
In Kay’s scenario, if the Cowboys do struggle again it could lead to a massive rebuild that includes quarterback Dak Prescott taking a seat in favor of second year quarterback Joe Milton III.
“With Prescott heading into his age-32 season and coming off a hamstring injury that could lead to further regression, the Cowboys could be farther from a championship than ever,” Kay wrote on June 24. “Given how desperate ownership is to make it back to the biggest stage — it’s been three decades since Dallas reached the NFC Championship Game, let alone the Super Bowl — and a potential replacement for Prescott waiting in the wings in Joe Milton III, it may not be long before the Cowboys elect to initiate a roster overhaul.”
Prescott’s Legacy: Coming Up Short in Playoffs
Headed into his 10th season as the Cowboys starting quarterback, Prescott’s legacy seems to have 2 main talking points.
The first is his pay. He’s become the highest paid player in NFL twice, when he signed a 4-year, $160 million contract in 2020 and when he signed a 4-year, $240 million contract in 2024, making him both the NFL’s first $40 million per year player and first $60 million per year player.
The second and most defining part of Prescott’s legacy is his utter failure in the postseason. Despite being one of the NFL’s top regular season quarterbacks throughout his career, Prescott has yet to advance the Cowboys to the NFC Championship Game — something no Dallas quarterback has done since Troy Aikman following the 1995 season.
From NFL.com: “I wanna win a championship,” Prescott said, via the team’s website. “The legacy and the things, and whatever comes after I finish playing, will take care of itself. I wanna win a championship. Be damned if it’s just for my legacy, for this team, for my personal being, for my sanity — the legacy will take care of itself. I have to stay where my feet are.”
Unfair Criticism of Milton’s Rookie Year
Some of the criticism of Milton before he was traded from the New England Patriots to the Cowboys seems pretty unwarranted and unfairly tarnished his reputation.
Mainly, the criticism of Milton for being a “locker room problem” seemed especially unsavory. Essentially, Milton got bad stories leaked about him because he allegedly thought he was better than first round pick and starter Drake Maye.
While a long-term veteran backup might be more inclined to take a backseat to Maye or any other embedded starter, asking a rookie to do so on a team as bad as the Patriots is pretty wild — and explains why they’ve been so bad since Tom Brady left.
