Ryan Poles is like most GMs in that he prefers the draft and will occasionally dip into the free agency market.

He's far more reluctant to spend greatly on free agents, but he has been willing to trade and has made two of the biggest deals in team history.

The biggest trade they ever made was by Poles and was in 2023, so Thursday's trade the Bears made for Jeffery Simmons must rank right up there behind it in impact. No doubt he'll find a way to add back picks with offseason trades but this was earthshattering in scope.

The Bears have had their hits and their misses when it comes to the trade market over the years. The hits seem much bigger but some of the misses were gut wrenching.

20 snaps of Jeffery Simmons dominating in run defense: pic.twitter.com/3ZGiAc7Ycm

— Ryan Paganetti (@RyanPaganetti) October 29, 2026

Of course, the 2023 trade Poles made is the biggest ever because it meant the Bears could draft Caleb Williams, among others.

Here are the top trades in Chicago Bears history ranked.

Titans got more for Jeffrey Simmons than Browns got for Myles Garrett.

— Tony Grossi (@TonyGrossi) October 29, 2026

1. Thank the Panthers

Trading Carolina the first pick in 2023 is easily the biggest deal the Bears ever made and the gift that keeps on giving.

Because the Bears acquired the first pick of the 2024 draft to use for DJ Moore, and picks they used to draft tackle Darnell Wright, cornerback Tyrique Stevenson, punter Tory Taylor, and wide receiver Luther Burden, this one stands supreme for impact. Getting Williams ushered in a new era on offense for the Bears. Wright is their blocking force in the wide zone running game. Burden is their yards-after-catch impact receiver. Taylor looks like one of the league's best punters now. Moore won them a playoff game over the Packers and helped them beat Green Bay to win a division title, then got them a second-round pick when he was traded and they used it for moves made to draft Sam Roush and Malik Muhammad.

2. The Jeffery Simmons trade

The trade itself is not entirely unlike the Khalil Mack trade that Ryan Pace made. Except it's the most anyone ever traded away for a defensive tackle. For Poles, it's a superstar defensive player acquired for a pair of first-round picks and a fourth-rounder. Gervon Dexter might have been the best Bears defensive tackle drafted since Tommy Harris, and they traded him largely because he didn't fit what they were trying to do in Dennis Allen's scheme to the degree that he would justify paying out a big contract. Now they have their best defensive tackle since the early Lovie Smith coaching era.

Great trade for the Bears, but they could’ve just drafted Carter

— David R. 🦅 🎧 (@PhillyFanHND) October 29, 2026

3. Khalil Mack trade

Khalil Mack and a conditional fifth-round pick in 2020 came to the Bears and the Raiders in return got first-round picks in 2019 and 2020, a third-round pick in 2020 and a sixth-rounder. The trade triggered a season when the Bears dominated defensively but thanks to Cody Parkey's double doink they still couldn't get past the Eagles in the playoffs and they also still lacked the offensive punch needed to get bigger things done than win a division title. Mack did help them get into the playoffs in 2020 as well, but his first season of 12 1/2 sacks was easily his best and nagging minor injuries held him down thereafter.

This is how Ryan Poles sold it to Ben Johnson. Cole Kmet replacement pic.twitter.com/Av6MhwkM08

— Joe Herff (@JosephHerffNFL) October 29, 2026

4. Never forget the way they thrilled the nation

Bears founder George Halas needed a quarterback to run his new T-formation. He found exactly the right player using a first-round pick he acquired in a trade with Pittsburgh. He sent offensive and defensive end Edgar "Eggs" Manske to the Steelers for what turned out to be the second pick of the 1939 draft. He drafted Colombia quarterback Sid Luckman and the result was a dynasty. The Bears won four NFL championships between 1940-46 thanks to 1943 MVP Luckman, and their new T-formation. Then they got Manske back and he played a big role in winning the 1940 title.

5. Jay Day

In 2009, it had become apparent Rex Grossman wasn't the answer. Jerry Angelo traded for Denver quarterback Jay Cutler. While Cutty had some decent years, he was only .500 in terms of wins and losses while playing with a good defense from 2009-12 under Lovie Smith, then played for two more coaches and struggled. The worst part of getting Cutler wasn't just the draft capital surrendered. They gave up first-round picks in 2009 and 2010 and a third-rounder in 2009 for him and a fifth-round pick. But they also had to pay Cutler two big contracts and eventually it kept them adding players they otherwise could have used. Cutler did get them to an NFC championship game and they lost after he was injured in the first half. The best QBs they could have taken with the first-round picks they dealt was Tim Tebow, so from that end it was fine. But they traded away Kyle Orton to Denver with this deal and they simply could have kept him and used him as starter because his statistics weren't a lot different than Cutler's from that point onward. Cutler had an 85.2 passer rating in Chicago while Orton was 86.3. Orton had a TD percentage of 3.9 and interception percentage of only 2.3. Cutler had a better TD percentage of 4.7 but also a 3.1% interception percentage.

6. A Monster trade

The greatest defensive player in Bears history came to them as a result of a trade. On Dec. 2, 1963, as they were a few weeks away from winning the NFL championship, the Bears traded a 1964 second-round pick and fourth-round pick to Pittsburgh for a 1965 first-round pick. The pick wound up being the third overall pick and the Bears selected Butkus, a force of nature and home-grown talent who scared the NFL into hiding until a knee surgery gone bad ended his career in 1973.

A first, literally: Jeffery Simmons is the first defensive tackle in the common draft era since 1967 to be traded for multiple first-round picks. pic.twitter.com/EOrDCK5MCl

— Adam Schefter (@AdamSchefter) October 29, 2026

6. The Coming of Danimal

The Bears used one great defensive lineman to acquire another. Veteran Pro Bowl tackle Wally Chambers was traded away after a brief Bears career greatly muted by injury. The Bears sent Chambers and tight end Bob Moore to the Buccaneers for a first-round pick prior to the 1978 draft. The pick was the fourth one of the 1979 draft, and the Bears used it for Hall of Fame defensive tackle/end Dan Hampton. He made two Pro Bowls at defensive end and two at tackle and anchored the 1985 Super Bowl champion defense.

Before everyone says we got fleeced, look at the numbers for draft capital to make this make sense! Y’all forget the math sometimes…

Not all first-round picks are created equal.

The NFL’s traditional draft-value chart assigns the No. 1 overall pick 3,000 points.

The No. 25… pic.twitter.com/vvZSh3ni3y

— relliK booN (@relliK_booN) October 29, 2026

7. Disaster, by George

The Bears, first, lost the coin flip so they could draft Terry Bradshaw in 1970. So they had the second overall pick. With Halas still running the show off the field, they decided it would be better to trade the second overall pick to Green Bay for linebacker Lee Roy Caffey, running back Elijah Pitts and center Bob Hyland. The Packers used the pick for Mike McCoy, who played defensive tackle seven years for them without making a Pro Bowl. But the second pick of the draft netted the Bears virtually nothing. They had 14 starts from Caffey and Hyland and Pitts never even played in a game for them. This was a complete and utter disaster, the worst trade ever made by the Bears and possibly the worst use of the second overall pick in any draft ever. What kept it from being a doomsday move was the team was so bad for about seven years that what did it matter, anyway?

Throwback to last year’s draft with a reminder from Packers legend Clay Matthews: THE BEARS STILL SUCK! pic.twitter.com/IF7GVpmMj6

— SleeperPackers (@SleeperPackers) April 20, 2026

8. Jay Day

In 2009, it had become apparent Rex Grossman wasn't the answer. Jerry Angelo traded for Denver quarterback Jay Cutler. While Cutty had some decent years, he was only .500 in terms of wins and losses while playing with a good defense from 2009-12 under Lovie Smith, then played for two more coaches and struggled. The worst part of getting Cutler wasn't just the draft capital surrendered. They gave up first-round picks in 2009 and 2010 and a third-rounder in 2009 for him and a fifth-round pick. But they also had to pay Cutler two big contracts and eventually it kept them adding players they otherwise could have used. Cutler did get them to an NFC championship game and they lost after he was injured in the first half. The best QBs they could have taken with the first-round picks they dealt was Tim Tebow, so from that end it was fine. But they traded away Kyle Orton to Denver with this deal and they simply could have kept him and used him as starter because his statistics weren't a lot different than Cutler's from that point onward. Cutler had an 85.2 passer rating in Chicago while Orton was 86.3. Orton had a TD percentage of 3.9 and interception percentage of only 2.3. Cutler had a better TD percentage of 4.7 but also a 3.1% interception percentage.

pic.twitter.com/V3xIAJmHSG

— Phil (@TheKingMvp) August 22, 2017

9. Just to Be Sure

In 1981 the Bears had a need for a middle linebacker to run Buddy Ryan's defense. They had their eye on Baylor's Mike Singletary but were afraid they wouldn't get him at No. 40, so just to be sure they gave San Francisco a fifth-round pick to move up two places and they drafted Singletary at No. 38 after they had already drafted eventual tackle starter Keith Van Horne 11th overall in Round 1. This pick might have ranked higher in the list except it involved a second-round selection and they only moved up two spots. It shows how much difference the slightest move up can make. The Vikings were the team drafting ahead of the Bears that they thought might take Singletary. Instead, Minnesota drafted wide receiver Mardye McDole 39th overall and he made three receptions for his career. Singletary made 10 Pro Bowls, a Bears record.

There were no easy yards when Mike Singletary was waiting on the other side.

🎙️ NFL Players: Second Acts

📺 https://t.co/onvYPhA90I pic.twitter.com/LrjZUTA08i

— NFL Legacy (@NFLLegacy) August 5, 2025

10. Another wasted first-rounder

Dave Wannstedt's time as coach included many wasted draft picks but there's no doubt what the worst trade made was during his six seasons. They traded away the 11th pick of the 1997 draft to Seattle and received quarterback Rick Mirer and a fourth-round pick. The fourth-round pick turned into Darnell Autry, the Northwestern running back. Autry averaged 2.9 yards per carry playing in two seasons for the Bears and Eagles. Mirer had already played four seasons with Seattle when the Bears made the trade and he had 41 touchdowns with 56 interceptions at the time. And that's what they wanted for the 11th pick? Mirer had a 37.7 passer rating for the Bears in three starts and seven total games. He was only slightly less ineffective for the Jets, 49ers and Raiders from 1999-2003 after the Bears dumped him.

Class move by former Bears director of college scouting @ggabefootball to take the L on the Jeffery Simmons trade. pic.twitter.com/J7oRK5qZK9

— Mark Potash (@MarkPotash) October 29, 2026