With well over a week to go before this year's NFL trade deadline, the Chicago Bears sent shockwaves through the league by trading for All-Pro defensive tackle Jeffery Simmons.
The former Tennessee Titans star fins himself within a winning organization and gets to leave behind a team contending for the no. 1 overall pick in next year's draft -- a place they're all too familiar with in recent years.
Meanwhile, Bears general manager Ryan Poles got the attention of his peers by going big with his trade for Simmons.
Yet, I have a feeling Poles might not be done. He's clearly going all-in on a Super Bowl, so why not take advantage of some other trade canddiates around the league?
- Jeffery Simmons trade details
- Bears' tradable picks after Jeffery Simmons deal
- Realistic Bears trade targets following Jeffery Simmons acquisition
- Latest Bears trade rumors
Jeffery Simmons trade details
To simplify things, and before we get into any more potential deals from Ryan Poles and company, here are the exact details from the Bears' trade for Jeffery Simmons.
Bears' tradable picks after Jeffery Simmons deal
Knowing all of the trade details above, here are the picks Chicago could still opt to trade.
2027
Round 2
Round 3
Round 5 (via ATL)
Round 6
Round 7
2028
Round 2
Round 3
Round 4
Round 5
Round 5 (via TEN)
Round 6
Round 7
Because Poles has already dealt a pair of first rounders, any other deals the Bears make will likely be for players who cost Day 3 capital, only. There is almost zero chance Poles decides to ship off second or third-round picks, at this point. Shoot, I highly doubt he's going to part with a fourth-round pick after the Simmons deal.
So, which players could the Bears go after, now, knowing that premium draft capital is off the table?
Realistic Bears trade targets following Jeffery Simmons acquisition
Khalil Mack, EDGE, Chargers
The Bears' top remaining trade target has been awfully quiet since starting the season with 3.0 sacks in his first four games. But, things continue to get worse for the Los Angeles Chargers.
Mack is on a 1-year contract and it makes all the sense in the world for Chicago to bring him back. The Bears have been able to generate sacks at a higher level than fans anticipated, this year, but are still not quite where they need to be in order to win a championship.
Donte Jackson, CB, Chargers
Cornerback is an alarming issue for this Bears team and clearly its weakest link. Between Jaylon Johnson and Tyrique Stevenson, the Bears don't have a viable starting option next to rookie Malik Muhammad.
Along with a few other Chargers players, Donte Jackson is someone the organization could end up parting with.
Before suffering a hamstring injury, Jackson had allowed an opposing quarterback rating of just 89.6 through four games.
Nahshon Wright, CB, Jets
This one makes too much sense, as the Jets have not used Nahshon Wright and he's grown mroe and more frustrated with his role in New York.
Last season, Bears fans saw Wright come up big with five interceptions and three fumble recoveries. He'd be well-worth a late Day 3 pick who already knows Dennis Allen's defense and could challenge Johnson and Stevenson.
Shemar Stewart, EDGE, Bengals
This is a weird one. Shemar Stewart was a first-round pick in 2025 but isn't being used in Cincinnati. Could he be available for trade? Potentially.
Would Cincinnati expect premium capital for a guy drafted in the first round, just last year? That's hard to imagine based on their actions with him.
Riq Woolen, CB, Eagles
Is he unpredictable? Absolutely. Is he a liability at times? He sure is.
Is he a better option than Johnson or Stevenson? I'd say he's a tier above, which makes him worth looking at.
Riq Woolen reminds many a lot of Tyrique Stevenson, but his size and speed have always jumped off the screen. He's had some great moments this season. He's also had some tough moments. But, the Bears are in need of cornerback help.
Latest Bears trade rumors
Khalil Mack to the Bears 'seems inevitable'
As Sunday's action got going in Week 8, The Athletic's Ted Nguyen offered up a few more potential trades we could see unfold around the league and he noted that the Mack-Bears reunion 'seems inevitable.'
There have now been multiple sources speculating over the cost only being a fifth-round pick for Chicago to be able to land Mack at the deadline.
Riq Woolen whispers aren't stopping anytime soon
Also in Nguyen's Sunday morning piece, he included a Riq Woolen deal where Chicago gives up a sixth rounder in exchange for the Eagles' starter.
Chargers have 'shut down' Khalil Mack trade offers so far
Sports Illustrated's Albert Breer reported that the Chargers have 'shut down' offers for Khalil Mack, to this point. But, there is no way that continues as the Chargers are now 0-7 and Mack being on a one-year deal.
Nahshon Wright discourse is definitely continuing
Brian Costello of The New York Post seems to believe what many of us believe when it comes to Nahshon Wright, and that's the idea he wants out.
"Wright is a possible piece the Jets could move. Wright said he has not asked for a trade, but he has spoken to the front office," Costello wrote over the weekend.
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