Skip to main content
Bear Digest

Rating All of Ryan Poles' Chicago Bears Trades: Win, Lose, or Draw

A list of all the trades made by GM Ryan Poles with a analysis of whether the Bears won, lost or tied on the move.
Gene Chamberlain|
Bears GM Ryan Poles hasn't been shy when it comes to making trades, and he's getting better at it.
Bears GM Ryan Poles hasn't been shy when it comes to making trades, and he's getting better at it. | Chicago Bears OnSI Photo: Chicago Bears video

In this story:

Chicago Bears

Bears GM Ryan Poles had just completed his selection of tight end Colston Loveland last year and fielded questions about his thinking in Round 1.

"We felt confident with the way that it was going to play out," Poles said. "We were looking at the numbers. We made phone calls, up and back, just to kind of see what the landscape was.

"Did it (trading) make sense for us or not? At the end of the day, the way that it fell,  we felt really comfortable with how it worked out."

This offered up insight into what happens every draft, every round. If there is one thing Poles is not afraid to do, it's trading, especially during the draft.

In most cases, it's been done to move back and gain picks.

Poles started making trades in 2022 and just kept on making them even when he didn't experience much success initially. He was trading late in the draft in his first year, and the chances for success will always be less.

Trading from a position of power increases chances or success, like with the deal in 2023 when he gave up the first pick in the draft to the Panthers, who wanted to select Bryce Young. It was a trade that kept on giving, even now after one of the keys to the deal, DJ Moore has left.

Here are all of Ryan Poles' trades, win, lose, and draw.

2022

•Traded OLB Khalil Mack to Chargers for a second-rounder and 2023 sixth-rounder. The Bears got necessary salary cap relief and also used the second-rounder to select Jaquan Brisker. They traded the sixth-rounder back to the Chargers. Brisker was productive when healthy and the cap relief let them start building. Draw

•Traded a 2023 second-round pick to Pittsburgh for WR Chase Claypool. The Steelers use it for Joey Porter. Claypool was a disaster. Loss

•Traded LB Roquan Smith to Ravens for a 2023 second-round pick, a fifth-rounder in 2023 and linebacker A.J. Klein. This was a trade made in exasperation after contract talks failed. Dexter has been productive and could prove to be a real asset. Sewell hasn't played, then did last year and was hurt Klein was quickly waived.  Loss

•Traded DE Robert Quinn to the Eagles for a 2023 fourth-round pick. Quinn gave the Eagles nothing, was hurt, and wound up out of football. They drafted Tyler Scott with fourth-round pick and he was cut before 2025. Draw

•Traded a seventh-round pick to the Patriots for WR N'Keal Harry. A real nothing deal. Loss

•Sent a 2023 sixth-round pick to the Chargers for the 254th and 255th picks Round 7. They drafted safety Elijah Hicks and punter Trenton Gill. Gill is gone but Hicks got another year in Chicago as a valued backup. The Chargers got backup defensive lineman and sometimes fullback Scott Matlock with it. Win

• Sent the 148th pick in Round 5 to Buffalo for pick No.  168 in Round 5 and No. 203 in Round 6, then drafted T Braxton Jones and RB Trestan Ebner. Ebner didn't work out but Jones was graded highly by Pro Football Focus until his 2024 ankle injury. He's still there with a second contract and might start again, but the Bills at 148 used the pick they got to draft wide receiver Khalil Shakir, who has 197 catches, 2,312 yards an 11 TDs in four years. The Bears sure could have used a wide receiver then, too. Loss

•Traded 150th pick in Round 5 to Houston for the 166th and 207th picks, then drafted center Doug Kramer at 207. He's gone. They traded No. 166 later. The Texans took D-lineman Thomas Booker, who quickly washed out and has had 1 1/2 sacks with three teams. Draw

•Traded the 166th pick for pick No. 174 and No. 226 with Cincinnati, then drafted DE Dominique Robinson and guard Ja'Tyre Carter. Robinson stayed around as a four-year backup and sometimes starter but didn't amount to much. Draw

2023

•Traded the first overall pick for DJ Moore, ninth and 61st picks in 2023, a 2024 first-round pick, 2025 second-round pick. They drafted Caleb William, Darnell Wright, Tyrique Stevenson, and Luther Burden III as a result, and now have a second-round pick for 2026 with Moore gone. Poles is punishing the team that wouldn't hire him. Win

•Traded WR Chase Claypool and a seventh-round 2025 pick to Miami for a sixth-round pick. Just getting Claypool off the roster and something in return rated a smashing success. Win 

•Traded the ninth pick of the draft to the Eagles because they didn't want Jalen Carter, and received a fourth-round pick in exchange. They used that pick for punter Tory Taylor in 2024. So, instead of Carter, they got an All-Pro tackle and the best punter in their history in career average. Neither one has been suspended for spitting, either. Draw

•Moved up in the draft, acquiring No. 56 overall from Jacksonville and dealing away No 61 and 136 in Round 5. Then they drafted CB Tyrique Stevenson. Jacksonville used it for backup linebacker Yasir Abdullah and tight end Brenton Strange, who has 91 catches in three years. Draw

•Traded 103rd pick in Round 4 to New Orleans for No. 115 and a fifth- rounder (165). They drafted RB Roschon Johnson and cornerback Terell Smith with the picks. The Bears got more use out of Johnson and Smith than the Saints did from Nick Saldiveri, who they took at 103. Saldiveri hasn't started a game and all three players wound up injured last year. Win

•Traded a sixth-round 2024 pick for C/G Dan Feeney. They didn't even use Feeney much and could have gotten the same from a waiver wire pickup. Miami used the pick for receiver, Malik Washington, who has 72 catches for 540 yards and three TDs. Loss

•Traded a second-round pick for DE Montez Sweat. He has been their only dependable pass rusher in 2 1/2 years and also stops the run, even if his pay is high. Win

2024

•Traded QB Justin Fields for a sixth-round 2025 pick. They had no use for him and is play since then has shown this was proper value. Draw

•Acquired DE Darrell Taylor from Seattle for a sixth-round 2025 pick. He had three sacks and 13 pressures. They gave up little and got little. Draw

•Traded a sixth-round pick to the Browns for DT Chris Williams and a seventh-round pick that later was traded. Williams was good enough in one year to get tendered as a restricted free agent, but left in free agency this year.  Win

•Traded running back Khalil Herbert to Cincinnati for a 2025 seventh-round pick, then used the pick for RB Kyle Monangai. Win

•Traded a fourth-round pick in 2024 for WR Keenan Allen. His seven TD catches and help provided to Caleb Williams in one year were valued but worth his ridiculous $23 million cap hit. Loss

•Traded fifth-round pick (No. 144) to Buffalo for G/C Ryan Bates. He played 105  snaps of offense in two seasons. They could have had the same from a rookie or waiver wire pickup.  Loss

•Used a fourth-round 2025 pick to get back into the 2024 draft and picked DE Austin Booker. It's already looking like a sharp move as Booker made huge strides in the second half of 2025. Win

2025

•Dealt a 2025 fifth-round pick (148) to the Rams for a 2026 fourth-round pick (No. 129) and a 2025 sixth-round pick, used for G Luke Newman. The Rams used it or DT Ty Hamilton, a sub with 11 tackles last year. The Bears could turn this into a steal at 129 this year. Win

•Traded a fourth-round pick to Kansas City for G Joe Thuney. A true masterstroke. Win

•Traded a sixth-round pick to the Rams for G Jonah Jackson. That's a bit better than giving up a sixth-rounder for Dan Feeney. Win

•Made a massive Round 2 trade, sending the 41st pick (T.J. Sanders), 72nd pick in Round 3 (Landon Jackson) and a seventh-round pick (240, Kaden Prather) to the Bills for No. 56 overall and took T Ozzy Trapilo, No. 62nd and took Shemar Turner and No. 109 overall in Round 4. They later traded the 109th pick back to the Bills. Trapilo and Turner both suffered season-ending injuries but played well before that. The Bills got DE Landon Jackson, who played three games, and DT T.J. Sanders, who had a sack in 12 games. Win

•Also traded the 109th pick in Round 4 back to Buffalo for No. 132 in Round 4 and No. 169 in Round 5. Linebacker Ruben Hyppolite II was the fourth-rounder and cornerback Zah Frazier the fifth-rounder. Deone Walker was the player Buffalo drafted at 109 and he started every game at nose tackle. Loss

•Acquired DE Joe Tryon-Shoyinka and a seventh-rounder Cleveland for a sixth-round 2026 pick. Tryon-Shoyinka gave them nothing beyond someone to provide Austin Booker and Montez Sweat with some rest. Loss

2026

•Traded a 2027 fifth-round pick to New England for C Garrett Bradbury. Caleb Williams needs someone competent to snap him the ball. Win

•Traded WR DJ Moore and a fifth-round pick to Buffalo for a second-round pick. Buffalo gets a potentially explosive starter with system knowledge, as well as a pick. The Bears get a second-rounder, No. 60 overall. The Bills have No. 165 and Moore. Even though Moore didn't figure to justify his big cap hit, that's the receiver who beat Green Bay twice in a month. Loss

More Chicago Bears News

X: BearsOnSI

Loading recommendations... Please wait while we load personalized content recommendations

Published
Gene Chamberlain
GENE CHAMBERLAIN

Gene Chamberlain has covered the Chicago Bears full time as a beat writer since 1994 and prior to this on a part-time basis for 10 years. He covered the Bears as a beat writer for Suburban Chicago Newspapers, the Daily Southtown, Copley News Service and has been a contributor for the Daily Herald, the Associated Press, Bear Report, CBS Sports.com and The Sporting News. He also has worked a prep sports writer for Tribune Newspapers and Sun-Times newspapers.

Home/News