The Chicago Bears are now two weeks removed from the earth-shattering Jeffery Simmons trade that unlocked their defense. They sent two first-round selections and a fourth-round pick to the Titans for Simmons and a fifth-round pick. If his first two games donning the blue and orange are any indication, they definitely underpaid.

Acquiring Simmons was one of Bears general manager Ryan Poles' best moves since taking the helm in 2022. It was far from his only consequential trade, though. He's always kept the phone lines open when it comes to trade conversations.

Here are the eight biggest trades Poles has made, ranked from eight to one in terms of significance.

8. No. 9 to Eagles for No. 10 in 2023 NFL Draft, 2024 fourth

A draft-day trade that saw them move down one spot might not seem as significant as other moves Poles has made, and it didn't include as much draft capital as others, but it was still monumental. Many believed DT Jalen Carter was the best player in the 2023 NFL Draft, and the Bears could've landed him with the ninth overall pick due to character concerns.

Poles trusted his judgment because he knew he had an ace in the hole. They instead drafted Darnell Wright, who has arguably become the league's best right tackle. They also knew the Eagles wouldn't take him, so they moved down one spot and picked up a fourth-round pick. They turned that extra pick into punter Tory Taylor, who has developed into a weapon in his third season.

Carter is a great player, but it's safe to assume they don't have any regrets at Halas Hall.

7. Khalil Herbert to Bengals for 2025 seventh

Khalil Herbert showed legit flashes over his first three years in Chicago after the team selected him in the sixth round of the 2021 NFL Draft. However, largely got phased out in year four, carrying the ball only eight times over the first six weeks. They shipped him to the Bengals for a seventh-round pick ahead of the trade deadline.

Why does this one rank so highly in terms of significance? The butterfly effect, of course. The Bears drafted Kyle Monangai with the pick they received for Herbert. Monangai was one of the biggest steals of the 2025 NFL Draft, and he picked up right where he left off this year before suffering a turf toe injury in Week 4.

6. DJ Moore, 2026 fifth, to the Bills for a 2026 second

The other DJ Moore trade (more on the first one later, obviously). They shipped Moore and a sixth-round pick to Buffalo for a second-round selection this offseason. With the depth that the Bears accumulated at receiver, many saw it as a necessary evil to create some cap space ahead of free agency.

Very few expected them to receive a second-round pick for Moore, though. Not after putting up a career-low 682 yards last season. Even fewer expected the Bills to inherit his four-year, $110 million contract. The Bears wound up trading the pick down, and eventually turning it into Sam Roush and Malik Muhammad II (after trading up to select him). All things considered, this was a great deal for Chicago.

5. Roquan Smith to Ravens for a 2023 second, 2023 fifth, and A.J. Klein

Not all significant trades work out in Chicago's favor. Roquan Smith was one of the league's best young linebackers in 2023, but he seemingly wasn't happy with the Bears' new regime after Ryan Poles took over. He briefly requested a trade ahead of training camp before eventually being a good soldier.

Poles decided the damage had been done, though. They traded the then three-time All-Pro to the Ravens for a second-rounder, a fifth-rounder, and AJ Klein, who only lasted two weeks in Chicago. The Bears turned those picks into two contributors, Gervon Dexter Sr. and Noah Sewell. It was still a bad move, though.

Sure, they didn't want to pay Smith $20 million per year. However, they didn't mind paying Tremaine Edmunds $18 million per year the next offseason. Only one of them has come close to living up to that contract, and it wasn't the one who was cut before he could finish it.

4. Khalil Mack to Chargers for 2022 second, 2023 sixth

Mismanagement by former GM Ryan Pace left Chicago's salary cap situation in ruins when Poles took over. They were a team going nowhere fast, and they needed to tear it down to build it back up. Poles knew liquidating Mack's massive contract was the quickest way to provide a jolt to the rebuild. They traded him to the Chargers for a second- and sixth-round pick in his first significant move on the job.

Did the trade age well? Not really. Mack was his usual dominant self over the next two seasons, accumulating 25 sacks. It's worth noting that Mack would've been rotting with a massive contract on a rebuilding Bears team (like he is now on a stingy and underwhelming Chargers team) over the next few years if they hadn't pulled the trigger, though.

Meanwhile, the Bears turned the picks into Jaquan Brisker, Elijah Hicks, and Trenton Gill (they turned the 2023 sixth-round pick into two 2022 seventh-rounders). Again, significant isn't always good.

3. 2026 fourth to Chiefs for Joe Thuney

To Poles' credit, he seemingly figured the whole trading thing out by year three. His ties to Kansas City might've helped him land a future Hall of Fame guard for a fourth-round pick in the 2025 offseason.

Thuney didn't allow a single sack last season, and he went on to be named the NFL's inaugural Protector of the Year for his efforts. He's also picked up right where he left off over the first half of 2026.

Their decision to trade a sixth-round pick to the Rams for Jonah Jackson (literally one day before acquiring Thuney) is a noteworthy honorable mention. Both players have fortified the interior of Chicago's o-line.

2. 2027 first, 2028 first, 2027 fourth to Titans for Jeffery Simmons, 2028 fifth

Speaking of Poles' ties to Kansas City, that connection also helped acquire Jeffery Simmons. He previously worked with Titans GM Mike Borgonzi in Kansas City, and the trust between the two is not only what got the deal over the finish line, but it's what got it over the starting line. Well, that, and Poles offering up two first-round picks right off the jump.

The trade could be a rare win/win for both sides. Simmons has completely unlocked Chicago's defense. It's obvious how this trade helps them. From the Titans' perspective, they now have ample draft capital at their disposal (and more cap space) to accelerate their rebuild.

1. No. 1 pick to Panthers for DJ Moore, No. 9, No. 61, 2024 first, 2025 second

Was there ever any doubt as to which trade would take the top spot on this list? Their decision to move off the first overall pick in 2023 largely shaped the Bears' current roster. Sure, Carolina being a dumpster fire that season (and subsequently helping Chicago get the first pick in 2024) helped, but that was still a calculated move by Poles. Acquiring Moore was a huge factor in their struggles, as Bryce Young had no reliable pass-catchers to throw to.

The Bears turned that one pick into Darnell Wright, Tory Taylor, Caleb Williams, Tyrique Stevenson, Luther Burden III, Sam Roush, Malik Muhammad II, and three years with DJ Moore. Hang it in the Louvre.