It’s safe to say the Dallas Cowboys are not going into the 2025 season looking at themselves like almost everyone else in the football loving world does — like a team that looks cooked from the start.
When reality does set in — probably in the first month of the season and maybe sooner — the Cowboys will do what they usually do and try and keep up appearances. Sometimes it’s almost like sleight of hand, with a fancy trade here or there to distract from what’s really going on.
To that end, the Cowboys seem like they could stir up some good will by making sure they have a competent backup quarterback behind former NFL All-Pro Dak Prescott, which they don’t have right now with Joe Milton and Will Grier.
Heavy Trade Pitch Paints Realistic Scenario
Heavy’s Max Dible thinks the Cowboys might make a splashy move and trade with the Cleveland Browns for quarterback and former first round pick Kenny Pickett, with Cleveland receiving a fifth round pick in return.
“Joe Flacco is the starter, so Pickett is liable to become available at some point,” Dible said. “That may not happen until the team transitions to its rookie QBs at some point mid-season, likely when they are past the opening six-game stretch of mostly playoff opponents and out of viable postseason contention. But Pickett will have value ahead of the deadline, and Dallas could be a destination. Dak Prescott missed nine games last year and has missed 27 over the past five seasons. Dallas traded for Joe Milton III, but he has been bad during two preseason outings and Will Grier is the only option behind him.
“History says the Cowboys will probably need a backup QB to start approximately one-third of the season for them. If Pickett can be that guy and go 3-2 or 2-3, that’s worth a fifth-round pick and then some — particularly if those two or three wins put Dallas over the top in a divisional and/or playoff race.”
Pickett On Third Team in Three Seasons
Things have gone sideways for Pickett in terms of his NFL career over the last few years. Taken in the first round (No. 20 overall) by the Pittsburgh Steelers in the 2022 NFL draft, Pickett was Pittsburgh’s full time starter his first 2 seasons until the team decided he wasn’t the right fit and traded him to the Philadelphia Eagles before the 2024 seasons.
Pickett was a dutiful backup behind Super Bowl MVP Jalen Hurts last season and got the opportunity he was chasing this offseason with a trade to the Browns, where he seemed like the favorite to become the starter in 2025.
That was before one of the stranger quarterback competitions anyone has ever seen began to unfold. After trading for Pickett, the Browns added 3 more quarterbacks in the next 6 weeks; veteran free agent and former Super Bowl MVP Flacco followed by 2 draft picks with third rounder Dillon Gabriel and fifth rounder Shedeur Sanders.
At this point, Pickett’s opportunities to be a full time starter may have run out. That doesn’t mean he won’t have a lengthy (and lucrative) career as a high level backup.
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This article was originally published on Heavy Sports
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