Bears floated as Riq Woolen landing spot after Jeffery Simmons trade

The Chicago Bears already made the biggest move of their deadline when they traded for Jeffery Simmons. Now there is talk of a smaller, cheaper move in the secondary. In a roundup of deadline proposals from ESPN, analyst Matt Bowen pitched a deal that would send Philadelphia Eagles cornerback Riq Woolen to Chicago for a 2027 fifth-round pick. The deadline is Tuesday at 4 p.m. ET.

The Simmons trade was expensive. The Bears announced that they sent Tennessee their 2027 and 2028 first-round picks plus a 2027 fourth-rounder for the three-time All-Pro defensive lineman, and they get a 2028 fifth-round pick back from the Titans. Simmons led all interior linemen with 11 sacks last season. Bowen's case is that the front is now set but the back end still lacks top-end speed. Woolen is 6-foot-4 and can play press-man on the boundary. He has 12 career interceptions and 59 pass breakups, and Bowen believes he would fit Dennis Allen's split-safety looks.

The proposal also lines up with what ESPN's Jeremy Fowler has reported. Bears On SI noted that Fowler named Woolen as a cornerback option for Chicago and said, "An available corner such as the Eagles' Riq Woolen for a Day 3 pick could make sense." The fit for Philadelphia is simple. The Eagles are 2-6, and Woolen signed a one-year deal there and becomes a free agent in 2027. Getting a mid-round pick now is better than possibly losing him for nothing in the spring. For Chicago, the price would be modest after two first-rounders already went out the door. This is still a proposal, not a reported negotiation.

What it means for Tampa Bay

No deal can happen before Sunday's game against the Tampa Bay Buccaneers at Soldier Field, which airs on NBC. Woolen wouldn't be available until the following week at the earliest. The Bears are 6-2 and have won three straight: 31-23 at Atlanta, 30-24 over New England and 34-17 at Seattle. They have scored 214 points and allowed 160, which works out to about 26.8 points scored and 20 allowed per game. Both losses came in division games, a 9-3 loss to Minnesota and a 31-7 loss at Green Bay. The defense has given up 24 and 23 points in two of the last three wins, and that is the gap Bowen thinks a corner like Woolen would help close.

The market makes Chicago a clear favorite. Across the 11 venues on our board for the game, Novig has the Bears at -257 to win outright. The best moneyline price anywhere is -250 at theScore Bet, so the venues are close. Novig lists Tampa Bay at +245. On the spread, Novig has the Bears favored by 6.5 at +108, while theScore Bet has Chicago at -6 for -105. The total is 47.5 at Novig, with -106 on the over and even money on the under. Theme sportsbooks carry a hold of 3.7% to 4.6% on the moneyline and as much as 4.8% on the spread and total.