Evaluating Ryan Poles’ Bears tenure as Chicago heads into Year 5

The Chicago Bears’ offseason talk has a clear center of gravity. Heading into the 2026 season, Ryan Poles is entering his fifth year as general manager, and the franchise’s baseline expectations have shifted because of what happened in 2025. According to the Yahoo Sports column assessing Poles’ tenure, Chicago won the NFC North and, perhaps more importantly, recorded its first playoff win since the 2010-11 season.

That success matters, because it changes how fans and executives measure both draft classes and trade swings. A winning record can hide structural problems, but a division title and a playoff victory also suggest the roster is capable of competing in the postseason, where roster construction gets tested in tight windows. When a team reaches that level, the evaluation conversation moves from “Did Poles rebuild?” to “Which decisions actually turned into wins, and which ones created long-term opportunity cost?”

The Yahoo Sports piece frames the question by looking at “the five worst moves” of Poles’ Bears tenure, essentially treating his draft and roster decisions like a portfolio. Even without agreeing with any one writer’s ranking, the premise is standard NFL analysis. Every general manager is judged on the combination of hits and misses, but misses are especially scrutinized when they overlap with prime team-building periods, when the quarterback situation stabilizes, or when other expensive parts of the roster begin to demand additional upgrades.

In that context, Poles’ Year 5 is a consequential stage. General managers often get defined by their ability to repeatedly add impact starters, not just to assemble a playable team. Bears success in 2025, including the franchise’s first playoff win in well over a decade, means the organization will be expected to sustain performance rather than chase it. That makes “worst moves” more than a trivia exercise. Moves that look forgivable during a rebuild become harder to defend when the team has stopped rebuilding and started contending.

There is also a practical roster logic behind why these lists matter. If a general manager makes a series of decisions that do not translate into reliable starters, the team can find itself repeatedly paying “retooling taxes,” spending premium draft capital or cap resources to fix problems created by earlier choices. That does not require a specific claim about Poles’ individual transactions to understand the underlying risk. In the NFL, the margin for roster construction mistakes is small, and the opportunity cost of a misstep often shows up years later, when younger talent might have been developed or when cap space could have been allocated to different needs.

Still, any retrospective ranking carries caveats. A “worst move” label is inherently comparative, and it depends on the counterfactual. One team’s value at a particular position might change with coaching schemes, quarterback performance, health, or league-wide trends. A player’s development trajectory can swing widely, even when the decision to acquire or draft them was reasonable at the time. That is why a single list cannot settle the broader debate about a general manager’s competence.

What to watch next is not the argument itself, but how Chicago’s offseason choices line up with the evaluation. Poles’ fifth year will be judged by whether the organization can convert its division-title momentum into sustained contention, and whether the Bears’ course corrections, if any, address the types of weaknesses that tend to show up in postseason losses. The 2026 season will function as the referendum on both the front office’s vision and the roster’s execution, with the “worst moves” debate serving as the backdrop.

In the end, the Yahoo Sports column’s timing is telling. Coming off an NFC North championship and a long-awaited playoff win, Chicago is no longer being measured by potential alone. It is being measured by continuity, and that is where the consequences of earlier decisions, good and bad, become unavoidable. If Poles truly has a few moves that did not pan out, this season is where the Bears can either compensate or suffer the lingering impact.