The Chicago Bears have signaled their intentions ahead of the NFL trade deadline on November 10. Acquiring All-Pro defensive tackle Jeffery Simmons from the Tennessee Titans was a bold move by a franchise determined to compete for a championship. Early results indicate that Chicago has every reason to feel confident about this decision. In Sunday’s game, the Bears secured a 27-24 victory over the Tampa Bay Buccaneers, improving their record to 7-2 and extending their winning streak to four games. Simmons had another impactful performance, significantly contributing to a defense that needed to compensate for five turnovers committed by Chicago's offense.
While the Bears have already addressed their primary weakness in the defensive front, general manager Ryan Poles still has the opportunity to strengthen another critical area. Acquiring Philadelphia Eagles cornerback Riq Woolen could provide the secondary with essential depth and experience without requiring a hefty investment of draft capital.
Chicago should consider offering the Eagles a fifth-round selection in the 2027 NFL Draft to acquire Woolen before the Tuesday deadline.
Bears should trade for Eagles cornerback Riq Woolen
Chicago’s decision to acquire Simmons was one of the most aggressive moves of the 2026 season. The Bears traded away their first-round picks for 2027 and 2028, in addition to a fourth-round pick in 2027, in exchange for Simmons and a fifth-round selection in 2028. This investment immediately bolstered the defensive line, providing coordinator Dennis Allen with another skilled player capable of disrupting opposing offenses. Simmons has already recorded two sacks in his first two games with Chicago, showcasing his ability to make an impact even with limited knowledge of the defensive system.
His presence on the field has also opened up opportunities for his teammates. Opposing offensive lines now have to account for Simmons in the middle, which may help draw attention away from edge rusher Montez Sweat. This improvement up front is crucial for Chicago's secondary, but it also highlights the ongoing weaknesses in their coverage. Jaylon Johnson made a pivotal defensive play against Tampa Bay, returning an interception 67 yards for a touchdown in the third quarter. Although the veteran cornerback has had an inconsistent season, this performance proved his ability to influence games when the Bears needed it most.
Why Woolen could improve Chicago's pass defense
Woolen's physical profile makes him an intriguing target for a defense that could benefit from added versatility. Standing at 6-foot-4, the former Seattle Seahawks standout has the length to challenge larger receivers and the athletic ability to compete against faster opponents.
His most impressive professional season came as a rookie in 2022 when he recorded six interceptions and defended 16 passes, establishing himself as one of the league's most promising young cornerbacks. Woolen continued to make an impact in Seattle, though inconsistent performances raised questions about his long-term future with the organization. During the offseason, Philadelphia signed him to a one-year contract, hoping his physical tools would strengthen their secondary. The results so far have been mixed. Through nine games, Woolen has recorded 34 tackles and defended eight passes but has not yet secured an interception. While he remains capable of disrupting passing lanes, occasional coverage mistakes have hindered his ability to establish the consistency expected from a reliable starter.
These shortcomings could be a concern for Chicago, especially because the team's current defensive issues already involve inconsistent coverage, but Woolen wouldn't necessarily be required to take on every challenging assignment immediately. Defensive coordinator Allen could pair him with Johnson and Stevenson, allowing the Bears to adjust their personnel based on opposing receivers and specific defensive situations. His size would serve as an additional option against teams with physically imposing outside targets, while his speed could help Chicago counter deeper passing concepts.
The arrival of Simmons further strengthens the argument for adding Woolen. A more effective pass rush reduces the time cornerbacks need to remain in coverage, giving defenders opportunities to capitalize on hurried throws and incomplete offensive adjustments
Why Philadelphia could accept Chicago's offer
The Eagles entered the 2026 season with hopes of competing for another championship, but their performance has significantly declined. Sunday’s 19-11 loss to the New York Giants dropped Philadelphia to 2-7, marking their seventh consecutive defeat. These disappointing results have fueled speculation that the organization may consider trading certain veterans before the deadline, particularly those nearing free agency. One player who fits this description is Woolen.
The 27-year-old signed a one-year, $12 million contract with Philadelphia during the offseason, and that contract includes void years for salary-cap purposes, meaning that even if he is traded, the Eagles will face financial consequences. Yet, the structure complicates any potential transaction, as it is not merely a matter of removing his remaining salary from the Eagles' payroll. However, the organization could still benefit from acquiring draft capital for a player who might otherwise leave after the season.
General Manager Howie Roseman must decide whether keeping Woolen for the rest of the season provides more value than obtaining a draft selection for the team's future. Given their current struggles, Philadelphia has little incentive to part with useful players without compensation, especially as uncertainty looms over the roster. Woolen has also expressed a desire to stay with his teammates, making it essential not to frame his departure as a certainty.
What Chicago should offer for Woolen
The Bears cannot approach another trade with the same willingness to surrender premium draft selections that defined the Simmons acquisition, as Poles has already invested heavily in improving the defensive line, and preserving future resources remains important even for a team with legitimate championship ambitions.
Chicago should therefore propose:
Proposed trade:
- Bears receive: CB Riq Woolen
- Eagles receive: 2027 fifth-round pick (via Atlanta)
The fifth-round selection originally belonged to the Falcons before Chicago acquired it during an earlier trade. This asset provides the Bears with a realistic opportunity to strengthen their roster without giving up another pick from the first three rounds. The financial commitment for acquiring Woolen would be manageable for the remainder of the season, although his contract contains some complexities that both teams will need to consider. Chicago would assume the remaining unpaid salary obligations tied to his agreement, while Philadelphia would retain any applicable bonus-related charges.
Additionally, the Bears must recognize that Woolen is scheduled to become a free agent after the 2026 season. A successful acquisition could lead to discussions about a longer-term partnership, but Chicago should avoid committing additional compensation based on the assumption that an extension will automatically follow.
Chicago has an opportunity to complete its defensive upgrade
They have shown that their defense can carry the team through challenging games, as illustrated by their victory over Tampa Bay on Sunday. This performance was particularly encouraging because Chicago's offense struggled with turnovers, including four interceptions thrown by Caleb Williams, yet the defense consistently responded under pressure, making essential stops to keep the team competitive. While Simmons has already strengthened the defensive front, improving the secondary would give General Manager Ryan Poles another opportunity to build a more reliable unit for the postseason.
Though Woolen comes with legitimate concerns regarding consistency and an expiring contract, these issues should influence the price Chicago is willing to pay, but they do not eliminate the potential value of acquiring an experienced cornerback. A fifth-round pick represents a reasonable investment for a player who could contribute immediately without requiring the organization to sacrifice another premium draft asset.
Poles has already demonstrated that he believes the Bears can compete with the strongest teams in the NFC. Acquiring Woolen would provide Chicago with an additional defensive option while still maintaining enough flexibility for future roster decisions.