What cost of Bears dealing away past picks can mean for this draft

In this story:
It's with the NFL draft approaching, where Ryan Poles' willingness to trade away middle-round draft picks in the past shows up as a real problem.
When a trade pans out, it's fine. It's merely the cost of doing business.
When it doesn't, the Bears not only failed at judging the talent of a player they brought in but they have cost themselves the chance to improve with a younger draft pick to develop.
There is another damaging side to it, and the Bears could wind up realizing this in the draft if they decide there is a particular player they'd like to draft but they fear someone might take him first.
In this case, the answer would be trading up to get this player. What will they have to trade
Equipped to move up
If the idea is moving up in Round 1, the Bears would be fine. They have a pair of second-round picks and a third-rounder who they could choose from if they wanted to move up as far as the fourth pick for, say Ashton Jeanty. The NFL trade value chart says they can make a deal like that. The two second-round picks they have are worth 510 and 490 points, and going from 10 to No. 4 would require 500 points or a second-round pick.
I speak for ALL Bears fans when I say we want Ashton Jeanty https://t.co/V90pnzbO0n pic.twitter.com/FQaJaN7ZU3
— Bearsszn (@bearssznn) April 4, 2025
Moving up to No. 7 might mean giving up their third-round pick based on the point value (230) for that 72nd selection.
However, it is in the second round where the Bears could face limitations moving up if they wanted to do it.
Ashton Jeanty during his college career had 3,557 yards after contact, which is 2nd all time in PFF’s system.
— Just Another Year Chicago: Bears (@JAYChi_Bears) April 4, 2025
It’s hard to not consider him if he’s there at #10
pic.twitter.com/z4btUioS4i
When they had a fourth-round pick, the 109th pick overall, they easily could have traded it to move up all the way from No. 39 in Round 2 to the first pick in the round.
How past trades hurt
For example, a player they have slated for a 30 visit to Halas Hall is Oregon tackle Josh Conerly Jr. Pro Football Focus grades Conerly as its 36th best player.
It's possible for the Bears to get Conerly at 39 but there could be other teams out there interested.
I’m not as big as most are on Josh Conerly Jr. He has a strong anchor and picks up stunts well but struggles on an island. He gets beat by guys quicker than him whether he’s there or down blocking to a linebacker. He may see success at guard in the league imo #NFLDraft pic.twitter.com/feMgnnVhGh
— Cooper Kress (@cooper_kress) April 4, 2025
Oregonian reporter James Crepea reported Conerly has 30 visits slated for Atlanta, Cincinnati, Houston, New Orleans, Philadelphia and Washington.
It might help having that fourth-round pick to move up if they wanted to take Conerly in Round 2 but they traded the 109th pick to Buffalo last year, one which turned out to be the 109th pick, in order to get back into the draft last year in Round 5 so they could select defensive end Austin Booker.
🚨OFFSEASON: Bears DC Dennis Allen has coordinated with Pass Rush Specialist Brandon Jordan to send Montez Sweat, Gervon Dexter, Grady Jarrett, and Austin Booker to the University of Miami throughout the spring, focusing on pass-rush technique and finishing at the quarterback. pic.twitter.com/9z0PSpMKjf
— Good Faith 🇺🇸 (@good_faith18) March 22, 2025
Although Booker had little impact as a rookie, it's too soon to say whether his acquisition made this move worthwhile after only one year.
It is not too soon to say the Bears sure could have used that fourth-round pick back now in case they needed to move up, or even just to fill the gap between their third-round and fifth-round picks. There is a big gap in which talent levels go past between early third round and early fifth round and they can't do anything about it because they no longer have that fourth-round pick,
Just remember who is making these calls. Ryan Poles tried to convince you Ryan Bates was the answer (TWICE!)
— BPA Scout (@ScoutBPA) March 5, 2025
Poles has demonstrated pliability when it comes to his coach’s needs. Except this time it’s OL instead of linebackers. Getting Ben Johnson was a franchise-altering move
Costly Ryan Bates deal
Another trade like this that proved costly was dealing away a fifth-round pick to Buffalo in March of 2024 to get guard/center Ryan Bates.
When they did this, they didn't have the fifth-round pick when they wanted to take Booker, and they had to make a deal to trade away this year's fourth-rounder to get back in and take Booker.
Trading picks to move up and down the draft board becomes tricky and costly.
Lack of picks in specific rounds can lead to more trades.
Nice trade for Joe Thuney. Hopefully, Poles understands now how important 4th-round picks are. The waste of 4th rounder last year on Ryan Bates was a big mistake. #DaBears
— John Restaino (@JohnRestaino13) March 5, 2025
It's all enough to make a team want to stand its ground and pick, or better yet move back at strategic points to pick up extra picks that can be used for positioning to select desired players.
It’s a course of action Poles even hinted at during the owners meetings.
"For where we are right now, I'm not confident exactly where the first nine picks are going to fall," Poles said. "But that's something that we'll look into and we'll definitely weigh the option of, 'Hey if we can move back and collect a certain pick in this range, could that be really beneficial for us as well?' So that'll be in play."
In this case, the strategic point is Round 1, pick No. 10, and it becomes a place where the Bears can atone for past mistakes by moving back for more picks.
More Chicago Bears News

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.