And he did it all by doing exactly what fans usually ask for from their general managers.
In my day-to-day life, I’m an English teacher. I spend a fair amount of time at the start of each semester reminding students that word choice matters and that they cannot assume others will share their definitions. I remind students that they need to be open to the idea that not everyone shares their same standards of judgment. I try to come up with examples all the time that show how two people looking at the same thing might have very different evaluations.
And Ryan Poles just took my job. Or rather, he taught exactly the same lessons with astonishing grace.
He just gave an absolute clinic on how definitions matter, and how dangerous it is to assume that others will share your same standards of judgment. He did this by focusing on the distinction between best player available and favorite player available. He also showed with astonishing clarity that while it is easy for armchair GMs to call for trading down in theory, it takes a special sort of grit to do it in real life. And then he added one more trick, but we’ll get to that later.
Heading into the 2025 NFL Draft, fans seemed to have reached a rough consensus. With a new head coach, a promising sophomore quarterback, and a free agency period that addressed the team’s biggest weaknesses, the goals seemed obvious and attainable. Even in a weak draft, Ryan Poles had an easy task. He needed to get a starter with high upside in the first round, get another pair of starters with the two second-rounders, and fill in the rest of the holes around those picks as best as he could. Most importantly, the draft’s few strengths–at running back and on the defensive line–seemed in tune with Chicago’s needs. Easy.
Lesson 1: Definitions matter
Despite a ton of fan hope, it is unlikely fan-favorite target Ashton Jeanty was ever really an option, and even if he had been, the cost would likely have been too high to manage while still achieving the other goals fans set out. Jeanty was therefore never the best player available because he really wasn’t available. He was, however, a favorite player that fans wanted to imagine was available.
Instead, Ryan Poles drafted Colston Loveland at #10. To be clear, I was on Team Loveland as early as March. He was my tenth overall prospect in this draft and had the highest rating from me of any offensive player left by the time Chicago drafted. I understand fans who wanted Tyler Warren, or Mykel Williams, or one of the Joshes at left tackle, but I was far from the only person who felt Loveland merited the tenth overall pick, and Loveland matched both the character profile and the team match profile that Poles desired.
By contrast, TreVeyon Henderson, my favorite running back for Chicago, went to the Patriots one spot before the Chicago Bears picked. This felt–emotionally–like a gut punch. I do not know if he was on Chicago’s board until that moment or not. Perhaps he was considered too much like D’Andre Swift or perhaps they were sure they could get him and so they didn’t try to trade up. Maybe they just didn’t evaluate him the same way that I did. Perhaps Poles should have traded up a little to be sure to get him. Or perhaps he simply did exactly what fans ask for from their GMs all the time and he was consistent with his own standards, not rushing ahead impulsively. Either way, he should be happy with the result.
After all, Luther Burden III does give Chicago perhaps the most complete set of passing targets a quarterback could hope for with Moore, Odunze, Burden, Kmet, and now Loveland. Burden was notably ahead of Henderson on Daniel Jeremiah’s Top 50 list, he was 27th on Dane Brugler’s list, and he was given a first-round grade in many outlets. And Poles picked him up in the second round. Burden was available, and he was probably the best player who was available, even if he was not my favorite player on the board at that time.
Lesson 2: Consistent Criteria Matter
Next, Poles met the goal asked for by fans all the time. He traded down. Had Chicago not traded down, they could have picked up one of a number of edge rushers or even one of the last remaining “target” running backs at #41. Instead they took a trade at a slight loss that pushed them into the 50s. Was Poles “too cute” here? Did Chicago get “sniped” as a result? It is an emotionally satisfying way to point the finger. It might even be correct. With multiple edge rushers and a pair of “fan favorite” offensive tackles taken before #52, it’s a compelling narrative. But it could just as easily be wrong.
At #52 Ryan Poles took a player who just a couple of years ago might have thrilled fans. Ozzy Trapilo is an almost perfect second-round tackle prospect. He has the requisite length and he has experience against high-level competition. Of the 38 college tackles drafted in the second round from 2011-2020, only eleven made it as regular starters at tackle. Those eleven share traits like extended playing time in college and length (with, of course, a floor of 33.13-inch arms). That describes Trapilo’s profile. The Boston College product seems (at least to me) to be an ideal candidate to compete for left tackle reps. I would prefer him at left tackle, though. He has light enough feet but lacks some power. He doesn’t interrupt, but he certainly deflects. Looking at my notes, of the eighty reps of his I watched, my nine “plus” reps included seven pass reps and two runs. I’m sure there are those who have watched more tape than me, but for what I watched, I liked what I saw.
Note that as a result of his maneuvering, before making his third second-round pick of a single draft class, Ryan Poles had successfully built out an offense by adding a tight end and a receiver with a first-round grade (each) and a plausible candidate for a starter at left tackle within a year. Consistency with the standards asked for by many Chicago fans would call that a well-prioritized and successful draft.
However, because he did not get Tyler Warren, Omarion Hampton, TreVeyon Henderson, Aireontae Ersery, or J.T. Tuimoloau–all players who he conceivably could have gotten at least two of had he approached the draft differently—some are going to be disappointed. Poles instead picked three players he and his staff had decided were the best available.
Notably, before the second day of the draft was over, Poles had added to the defensive line (a strength of the draft) at spot #62 with the 56th player on Brugler’s list. The defensive tackle was actually taken a spot ahead of Omarr Norman-Lott, whom the Bears hosted for a 30 visit. So this was, seemingly, an informed decision, and given that these two players were frequently next to each other on most ranking boards, it makes sense that they were taken in succession. However, Poles took the player he wanted, not one that he somehow settled for.
In fact, it’s unlikely that he settled for a player at all.
Lesson 3: Remember the Big Picture
Multiple trades later, Poles had converted his last three picks (109, 148, and 233) into a linebacker, a corner, an interior offensive lineman, and (finally) a running back—in addition to a future pick as well. In the course of calculating all of his maneuvering in terms of “trade value”, I realized that the chart was simply the wrong way of looking at it, because it blinded me to the masterclass Poles had put on. It’s important to look at this draft in terms of the timing of each of Chicago’s picks in order compared to where they were originally located and where they were located after all of the trades he performed.
Note that besides delaying #41 to #56 (taking Ozzy Trapilo instead of Aireontae Ersery, essentially), every later pick is actually ahead of schedule, and post-trades Poles actually made an eighth pick that he was not otherwise scheduled to make. Of course, he got ahead in another way, because this chart also excludes the extra 4th-round pick that Poles acquired for 2026. Looked at objectively and holistically, Poles most emphatically did not fall behind from his trading down, allowing himself to be sniped. Instead, taking a single shift down allowed him to (on net) trade up at every successive point in the draft, and he did so in a way that added two extra picks when he was done.
Conclusion
I always remind my students to check their biases and look at the whole picture, keeping an open mind. I always remind them to be consistent with their own criteria and to be clear in their definitions. Ryan Poles just put on a masterclass as to why that matters. Poles prioritized the offense and walked away with two first-round-graded offensive weapons. At the cost of “settling” for one developmental offensive tackle over another, he ended up moving the rest of his entire draft forward and still gained an additional selection in this draft and in the next one.
Whatever criticisms I might have had of Poles in the past, I can only tip my hat in utterly astonished respect at how well he maneuvered through the 2025 draft. I might not agree with all of the selections he made, but he absolutely made those selections on his own schedule and in a way that made more players available to him at each point, not fewer.
Bear Down.