General manager Ryan Poles might be the most popular he has ever been during his tenure with the Chicago Bears.

Poles recently pulled off a blockbuster trade with the Tennessee Titans for superstar defensive lineman Jeffery Simmons that we believe will end up being one of the best trades in franchise history, let alone of his tenure.

Simmons is already making a massive impact over two games and even though it took a historic package to get the deal done, the trade is starting to look like a steal for Chicago.

Interestingly enough, that trade might not have happened had he not made a big mistake upfront before the season started.

Ryan Poles' biggest mistake of 2026

The addition of Simmons no doubt changes the outlook of the Bears' defensive line, but Poles trading Gervon Dexter to the Atlanta Falcons was the biggest mistake he has made in 2026.

Of course, the Bears unloaded Dexter in a trade with the Falcons before the season started.

While we understand he was never a good fit in Dennis Allen's defense, there were still several problems with that decision.

Not enough of a return

The first issue was the return Poles got, which was a fifth-round pick and defensive back Clark Phillips.

Chances are that fifth-round selection won't amount to anything, and Phillips has played 58 snaps on defense and has two tackles and one QB hit.

For a starting-caliber player like Dexter who is a plus pass-rusher, we feel like the Bears should have gotten more, and at the very least, a starting-caliber player in return or a better pick.

The risky replacement plan

The next problem is the Bears overestimated the kinds of impacts they would get out of the guys they had pegged to replace a player who was the team's best interior pass-rusher.

Chicago expected Kentavius Street and Jordan van den Berg to step up, but neither really answered the bell.

Street had one sack, which came in Week 1, and he posted a bad run defense grade of 46.2. He is now likely to miss the rest of the season because of a knee injury.

The rookie has been even worse. After playing 22 snaps in Week 1, van den Berg hasn't played more than 11 since. Over his last four games, van den Berg has played eight and five snaps, was a healthy scratch, and then played a season-low three snaps.

In all, van den Berg has one tackle, one pressure and one QB hit in eight games played, and the Bears saw their interior defenders post one sack combined before Simmons arrived.

Hindsight is always 20/20, but it was always a risky proposition to depend on Street and even Neville Gallimore, both of whom have been backups during their careers, and a sixth-round rookie to replace a starter like Dexter.

Gervon Dexter's strong season

Meanwhile, Dexter is having a pretty good season with the Falcons.

He does only have 1.5 sacks, so he's on pace to finish with less than he had in 2025, but Dexter also is tied for 10th in pressures among interior defensive linemen, and he is posting the best run defense grade of his career with a 66.4, per Pro Football Focus.

Dexter has more sacks and pressures than the guys who were tasked to replace him combined.

The Jeffery Simmons save

Because of the Dexter trade and the failure of the guys who were pegged to replace him to step up, the Bears found themselves with a big need along the interior before the deadline.

Thankfully, Poles was able to seal that up in a big way with the trade for Simmons that took a historic package to get done.

We love that trade, but let's not pretend Poles wasn't fortunate to be able to make it. It absolves him of the mistake he committed with the Dexter trade, but it doesn't erase the fact that Poles is guilty of having made that mistake in the first place.

Perhaps that trade never happens if Dexter stays, but we can't say that for sure. We could have seen a scenario where Poles acquires Simmons and then flips Dexter after, and it's also possible that Poles could have gotten more for Dexter at the trade deadline.

Whatever the case may be, Poles has managed to come out smelling like a rose.