By all accounts, the Chicago Bears drastically improved their defense by trading for Jeffery Simmons on Thursday. While the Bears’ defense already ranked ninth in points allowed this season, Simmons is one of the best defensive tackles in the NFL, and he’s coming off a career-high 11-sack season.

With Ben Johnson fully confident that he has an offense, led by Caleb Williams, that’s capable of competing for a Super Bowl, the Bears have now made a move that they feel gives them a defense they can win with too. While fans are justifiably excited about what adding a First-Team All-Pro DT to Dennis Allen’s defense can do, some analysts are raising caution.

ESPN Gives Chicago Bears a ‘C’ for Jeffery Simmons Trade

The Bears aren’t the only team that’s made a blockbuster trade ahead of the Nov. 10 deadline. The Seattle Seahawks added a potential future Hall of Famer in Quenton Nelson, trading a 2027 third, plus a 2028 fifth-round pick in the process. Then, the San Francisco 49ers were the next team to take advantage of the Indianapolis Colts’ fire sale by sending a 2027 fourth-round pick in exchange for DeForest Buckner. Both were on expiring contracts, which impacted the cost each team paid.

However, the Bears have paid the most to complete their blockbuster, by far. Chicago agreed to send not just their 2027 first-round pick, but also their 2028 first-round pick, plus an extra fourth-round selection this year in exchange for Simmons plus a fifth-round pick in 2028.

Is that too much to pay for a 29-year-old? ESPN seems to think so. Not only did they grade the Bears with a ‘C’ while handing out an ‘A’ to the Titans, but ESPN’s Seth Walder also suggests Chicago GM Ryan Poles overpaid to get the deal done.

“So, Simmons absolutely makes sense for the Bears, and in general, I am strongly in favor of Chicago making deadline additions this season. But there is a compensation limit where a trade ceases to make sense, and I think the Bears ran past it. Simmons joins a small fraternity of non-quarterbacks to be traded for multiple first-round picks in recent years: edge rushers Micah Parsons and Khalil Mack, offensive tackle Laremy Tunsil, safety Jamal Adams and cornerback Sauce Gardner. The results have been mixed at best for the acquiring team and Simmons, at 29 years old, is the oldest of these players at the time of the deal (Mack was the previous oldest, as the Bears acquired him as a 27-year-old in 2018).”

Seth Walder on Chicago Bears’ Jeffery Simmons Trade

Naturally, time will tell whether this trade truly pays off for the Bears. Yes, they’re ditching two future first-round picks. If they win a Super Bowl, no one will bat an eye at that decision. Yet, if the Bears somehow miss the playoffs in either season, not having their first-round pick in the following draft will sting.

Meanwhile, for now, the Bears look like one of the NFL’s very best teams on paper. If that’s how the games play out too, then this trade will work out well for all parties involved.