The Chicago Bears are sitting at 6-2, comfortably holding their own in the middle of a brutal NFC North.
After landing defensive game-wrecker Jeffery Simmons, the front office has already signaled they are in full-blown acquisition mode. With the trade deadline looming this Tuesday, the question isn’t whether they have enough talent, but whether they can squeeze every drop of potential out of this roster before the window for a serious Super Bowl run narrows.
While the roster is undeniably deep, the Bears are still keeping their eyes on the market. According to reports, they are looking to package late-round draft picks to shore up two specific areas: cornerback and edge rusher. It is a calculated gamble on depth, aimed at insulating the team against the inevitable attrition of a long season.
The Hunt for Secondary Depth
The cornerback position has been a persistent puzzle for Chicago this season. The most logical target on their radar is Alontae Taylor of the Tennessee Titans. Taylor offers a familiar tactical advantage, having played under defensive coordinator Dennis Allen for three years in New Orleans.
His experience across both the slot and the perimeter makes him a versatile chess piece, though his high-dollar contract—a three-year, $60 million deal signed this offseason—could complicate the math.
If the price for Taylor proves too steep, the team has other, more budget-friendly avenues to explore. Nahshon Wright remains a name to watch, largely due to his existing history with the club.
Wright has struggled to find a defensive foothold with the New York Jets, having not played a single defensive snap since signing his $3.5 million contract. Bringing him back would likely cost little more than a late-round pick swap, making it a low-risk move to inject some familiarity into the secondary.
Then there is Riq Woolen, who represents the highest ceiling among the available options. After signing a one-year, $12 million contract with the Philadelphia Eagles, Woolen has shown flashes of brilliance alongside a frustratingly low floor. With the Eagles currently mired in a lost season, they may be willing to part with him for the right price, though he would certainly command a higher premium than a veteran like Wright.
Finally, there is the case of Washington’s Mike Sainristil. After a standout 2024 rookie campaign where he notched four interceptions, Sainristil has seen his role evaporate, playing only 39% of defensive snaps this year. With teams often willing to “sell low” on underperforming assets, he represents a classic dart-throw for a front office looking to maximize value.
The Edge Rusher Equation
The pursuit of an edge rusher is a more curious development, especially following the addition of Jeffery Simmons. A reunion with Khalil Mack, currently with the Los Angeles Chargers, was the subject of much speculation, but Chargers head coach Jim Harbaugh has remained adamant that his 0-7 squad is not in sell mode. Whether that stance shifts after Sunday’s game is uncertain.
There is also the lingering interest in Jermaine Johnson II. The Bears were reportedly scouting Johnson ahead of last year’s deadline, and his status as an impending free agent makes him a prime candidate for a team looking to improve its pass rush. The Titans, currently sitting at 1-7, might be willing to take a fifth-round pick for a player they are likely to lose anyway.
The economic reality of these trades is simple: teams like the Bears are betting that a marginal upgrade today pays dividends in January.
By identifying players who are either miscast in their current schemes or stuck on rebuilding rosters, Chicago is positioning itself to capitalize on the desperation of others. Whether these moves materialize into a deeper playoff run, however, depends on whether these additions can transition quickly into a high-stakes environment.

The trade deadline serves as a final, frantic checkpoint. For a team already sitting at 6-2, the goal isn’t just to add bodies; it is to find the specific pieces that prevent a weakness from becoming a liability when the postseason arrives.