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Derek Carr is a cautionary tale for Chicago Bears and Caleb Williams

Originally posted on Chicago Bears on SI
By Pete Martuneac | Last updated May 11, 2025 2:38 PM ET

After 11 years in the NFL, quarterback Derek Carr shocked the NFL world on Saturday by announcing his retirement. He was already expected to miss the 2025 season due to a major shoulder injury, and Carr has apparently taken that as a sign that his time playing football is over. While never among the game's truly elite quarterbacks, Carr at his best was a good, reliable starter, as evidenced by his four Pro Bowl bids.

Despite all his individual success, however, Carr never won a single playoff game, appearing in only one, a Wild Card loss to the Cincinnati Bengals in 2021. His 11-year career was better than the vast majority of quarterbacks that come and go in the NFL, yet he never had the slightest taste of postseason success.

Now, Carr's decision to retire while still relatively young should serve as yet another cautionary tale to the Chicago Bears. Carr was a talented quarterback even by NFL standards, but the Raiders never put enough talent around him to get him to football's highest stage, the NFL playoffs. In the ultimate team sport, Carr was often asked to carry subpar rosters as far as he could manage.

What does that mean for the Bears? Quarterback Caleb Williams entered the NFL in 2024 as the consensus first overall pick, a generational talent according to some analysts and scouts. Fair or not, he is expected to put together a career full of individual and team accolades. He has the talent to do it, but no quarterback can succeed alone.

If the Bears go the path of the Raiders, constantly missing on draft picks and free agency signings, Williams will be one more addition to Chicago's quarterback graveyard, another promising career wasted by organizational incompetence.

Luckily for Bears fans, Chicago GM Ryan Poles has seemingly taken the Bears off this road just one season into Williams' career. Since January, Poles has made a string of decisions that strike every analyst and expert as smart. He hired the best available head coach to lead the Bears and call plays for Williams. He targeted and either traded for or signed the best available offensive linemen. He drafted two of the best pass catchers available in the 2025 NFL draft.

They still need to prove it on the field, but the 2025 Bears already look like a team that's a good quarterback away from making a deep postseason run. If Williams lives up to the hype, they just might do so.

This article first appeared on Chicago Bears on SI and was syndicated with permission.

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