More injuries around the NFL means that the Dallas Cowboys continue to face a decision at quarterback. The position continues to be a point of strength on Dallas’ roster with the team having both Sam Howell and Joe Milton as insurance behind Dak Prescott.
The Chicago Bears are dealing with a scary injury to franchise quarterback Caleb Williams. Could the Bears have an interest in one of the Cowboys quarterbacks?
Given the Cowboys have Milton on the team’s practice squad, Howell is a more likely potential trade candidate.
If the team moved on from Howell, Milton would be a prime candidate to take over as the Cowboys backup quarterback, a role the signal-caller had in 2025.
Let’s dive into what a potential Cowboys-Bears trade could look like.
NFL Rumors: Could the Bears Strike a Quarterback Trade With Cowboys?
It is hard to imagine the Cowboys could land much more than a late Day 3 draft pick for Howell in a trade. Chicago already has Tyler Bagent and Case Keenum on the team’s roster.
It is hard to argue that Howell is a major upgrade over either of these veterans. Howell is on a team-friendly one-year, $2.5 million contract with the Cowboys.
The signal-caller has earned more than $6.5 million over his career. Howell has played in 20 NFL games, including 18 starts, during his career.
Bears QB Caleb Williams Is Dealing With a Suspected Hamstring Strain, Says Sports Doc
Just how aggressive the Bears get in the trade market depends on the severity of Williams’ injury. The star quarterback left the team’s Week 2 game against the Minnesota Vikings with a hamstring injury.
“Caleb Williams. Hamstring strain. Carted off,” sports doctor David Chao detailed in a September 20, message on X.
“Unfortunately that’s a hazard of wet weather. TBD to see how bad the tear is.”
Cowboys Named Sam Howell as the Backup Quarterback Over Joe Milton
Howell struggled in his time as a starting quarterback for the Washington Commanders. Yet, Howell has enough talent to help an NFL team like the Bears win games while their franchise quarterback is temporarily sidelined.
Cowboys head coach Brian Schottenheimer explained why Howell got the nod over Milton as the team’s QB2 behind Prescott.
“When we looked at the whole body of work we felt like Sam had done a little bit better of executing the offense,” Schottenheimer told reporters on September 1, per ESPN’s Todd Archer.
Prior to Howell winning the QB2 role, Schottenheimer outlined the strengths of both quarterbacks. It will be interesting to see just how long the Cowboys can hide Milton on the team’s practice squad.
Teams Like the Bears Could Looks to Poach QB Joe Milton
Milton did pass through waivers unclaimed when the Cowboys briefly released the quarterback only to re-sign the signal-caller to the team’s practice squad.
“I think it’s a great competition…” Schottenheimer noted on August 24, per Cowboys.com’s Tommy Yarrish. “Joe’s performed beautifully in both games, you can’t look at the numbers and not know that… but Sam’s made a lot of play’s too.
“Sam did a beautiful two-minute drive against Seattle. Like I said, we don’t have to, and we’re not ready to make any decisions yet.”
Proposed Trade Has Bears Land Cowboys $6 Million 20-Game QB Amid Caleb Williams’ Injury