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Chicago Bears: 5 second round trades to stack draft capital

Ryan Heckman
Ryan Heckman

Da Windy City

Chicago Bears, 2023 NFL Draft (Tim Heitman-USA TODAY Sports)

Three and a half weeks is all we have to wait, now. The Chicago Bears have been one of the most dominant teams during the offseason, and the 2023 NFL Draft awaits them.

Ryan Poles has heard praises being sung over the past few weeks after the work he’s done to improve the roster in such a significant manner, but the work is not done, just as he acknowledged at the owner’s meetings recently.

Last year, we saw Poles enter the draft with far less picks than he came away with. Trading is not something he’s backed down from. In fact, he relishes the opportunity to take more swings, as evidenced by the amount of moves he made on Day 3 a year ago.

But, what if he continued to make those types of moves, yet did so a little earlier in the draft this year? The Bears have two second-round picks, which could prove to be very valuable in acquiring additional capital. What type of trade could Poles pull off with one of those picks? Let’s examine a few possibilities.

The Chicago Bears could trade back in the second round, resulting in even more draft ammunition for Ryan Poles

Trade Number 1

In this first scenario, the Bears do a little business with the defending Super Bowl champions.

First off, let’s establish the fact that this is the type of move Super Bowl teams make. The Chiefs have a championship roster. They’re at the pinnacle. Why not make a bold move to go up and get a guy they really like?

What if a move like this means the Chiefs go up to draft Josh Downs, Rashee Rice or another playmaker for that offense? Just imagine the possibilities for Patrick Mahomes and Andy Reid with yet another young weapon on that unit.

The Bears walk away moving down 10 spots, here, but also net a fourth and fifth-round pick in this year’s draft. That’s a heck of a haul while also being able to select another quality player just a few picks later.

Players to target at no. 63: Syracuse offensive tackle Matthew Bergeron, Bowling Green edge rusher Karl Brooks, Alabama cornerback Eli Ricks, TCU cornerback Tre’Vius Hodges-Tomlinson, Wisconsin edge rusher Nick Herbig, Minnesota guard/center John Michael Schmitz

Chicago Bears, DeMeco Ryans
Chicago Bears, DeMeco Ryans (Photo by Bob Levey/Getty Images)

Trade Number 2

At one point, Bears fans were getting ready to finish with the second overall pick in the draft at the tail-end of the regular season. But, Lovie Smith did the Bears one last favor and the Texans moved from first to second in the 2023 draft order after winning their final game of the season.

Now, the Texans are still in position to get a franchise quarterback at no. 2. They also have the 12th overall selection, giving them some franchise-altering power there. After possibly selecting someone like C.J. Stroud at no. 2, and then maybe a Christian Gonzalez or Calijah Kancey at 12, the Texans will pick again at 33. But, what if they were able to jump back into the second round and snag another top player?

For the Bears, this would work out well, because they’d only be moving back 12 spots to an early third-round pick. But, they’d also acquire an early fourth-round selection in the process. At that point in the draft, there are going to be a lot of players along the same line of pre-draft grade. Between that 55-80 area is where it can get muddy.

Teams could either draft a stud, or reach and end up failing big time.

Players to target at no. 73: Baylor defensive lineman Siaki Ika, Georgia cornerback Kelee Ringo, Tennessee wide receiver Jalin Hyatt, Auburn edge rusher Derick Hall,  South Carolina cornerback Darius Rush

Chicago Bears, Joe Burrow
Chicago Bears, Joe Burrow (Photo by Cooper Neill/Getty Images)

Trade Number 3

Going back to the likes of the Chiefs in our first segment, the Cincinnati Bengals are only a year removed from finishing runner-up and making a Super Bowl appearance, themselves. Joe Burrow and the Bengals look like an AFC powerhouse for years to come, and again, bold moves are to be made when you’re in position to win a Lombardi.

In this trade, the Bears trade the better of their second rounders to Cincinnati, who really like a particular player at this stage in the draft (an offensive lineman, maybe?).

In exchange, Cincinnati parts with their pick at no. 60 in the second round, plus a fifth and sixth rounder this year. So, the Bears move back just seven spots but Poles is able to net a couple of extra picks on top of swapping to no. 60.

Like I said previously, the difference between 53 and 60 could be monumental, but it could also be incremental. Chicago will still have the chance to come away with a legitimate starter here at 60, and then Poles gets two more bat swings later on.

Players to target at no. 60: USC edge rusher Tuli Tuipulotu, Army edge rusher Andre Carter II, TCU cornerback Tre’Vius Hodges-Tomlinson, Kansas State cornerback Julius Brents, Notre Dame edge rusher Isaiah Foskey

Chicago Bears, Bill Belichick
Chicago Bears, Bill Belichick.(Photo By Winslow Townson/Getty Images)

Trade Number 4

Ah, yes. The man who is never afraid of making a move, regardless of how he might look to the rest of the world. It’s Bill Belichick, both judge and jury in New England. Fortunately for his ego and reputation, the Patriots don’t necessarily make a bone-headed move here. In fact, it’s a relatively tame trade that works out for both sides.

The Bears deal their second pick of the second round to New England in exchange for the Patriots’ third rounder coming in at no. 76, along with their fourth-round pick at no. 107 overall.

Back to the Patriots, for just a second, because everybody loves attempting to poke fun at one of the league’s best coaches of all-time. This very well could be a move that lands Belichick flat on his face. We all remember the picks such as N’Keal Harry, Dalton Keene, Devin Asiasi and Sony Michel. You never know … this could be another wasted pick, and the Bears may look like geniuses.

Players to target at no. 76: Wisconsin defensive lineman Keeanu Benton, SMU wide receiver Rashee Rice, Utah cornerback Clark Phillips III, Maryland offensive tackle Jaelyn Duncan, Texas defensive lineman Moro Ojomo

Chicago Bears, Sean Payton
Chicago Bears, Sean Payton (Photo by Matthew Stockman/Getty Images)

Trade Number 5

Finally, we come to one of the most polarizing franchises in the NFL over the past year or so, the Denver Broncos. Bringing in Sean Payton to be their next head coach cost them greatly, but they need close to a miracle if the team is going to turn around the dumpster fire that was their offense last season.

Can Payton and the Broncos move up just six spots, here, and get a game-changing talent to help them out?

In this deal, the Bears move back to no. 67 while also netting an early fifth-rounder from the Broncos. There won’t be much difference in players available at no. 67 versus no. 61, and being able to have one more chance at a pick later one makes this worth it.

The Broncos, meanwhile, need to pull out all the stops if they are to get this fan base back to believing again. Do they go after an edge rusher, here, with such a rich pool of talent at the position? Or, maybe it’s an offensive lineman to help Russell Wilson out a little bit.

Players to target at no. 67: Alabama cornerback Eli Ricks, Kansas State cornerback Julius Brents, Baylor defensive lineman Siaki Ika, Auburn edge rusher Derick Hall, South Carolina cornerback Darius Rush

*Note: All trades were created using Pro Football Reference’s draft pick trade value chart, and every trade was either even in value or too close to call.

Ryan Heckman

Ryan Heckman

Ryan Heckman is a Lead NFL Editor for FanSided, covering all 32 teams across the league. Ryan has covered various leagues and teams dating back to 2012, with experience covering both the NFL and NBA. His work has been featured on Bleacher Report and Sports Illustrated among other publications. He loves Jesus, family, and the NFL in that order. If he isn't writing, Ryan is spending time with his wife and kids, drinking coffee or lifting weights.