Bears trade two first-round picks for Jeffery Simmons

The Chicago Bears traded two first-round picks to the Tennessee Titans for All-Pro defensive tackle Jeffery Simmons, and ESPN’s Bill Barnwell took a long look at whether these deals actually work.

The Bears have a great offense led by Caleb Williams and a defense that needed help. Simmons is what Barnwell calls a “shop-wrecker,” the sort of interior pass rusher coordinator Dennis Allen has sought for years. The 2026 Bears are better with him in the lineup.

But Barnwell’s piece is a history lesson, and the history is not encouraging. The Bears kicked off the modern era of two-first-round-pick trades in 2018 when they sent two first-rounders to the Raiders for Khalil Mack. Mack was great in his first game and good for one season. Then injuries, decline and a trade to the Chargers for a second-round pick. Barnwell calls it “closer to disappointing than successful.”

The hits since then are mixed. Jalen Ramsey to the Rams worked. Matthew Stafford to the Rams worked. Laremy Tunsil to the Texans was a disaster, though not because of Tunsil. Jamal Adams to the Seahawks failed. Russell Wilson to the Broncos was a catastrophe. Deshaun Watson to the Browns is, in Barnwell’s words, “arguably the worst trade in NFL history.”

Simmons was the best player on Titans tape, but Barnwell notes he was not single-handedly elevating a defense that ranked 31st in DVOA before the trade. The Titans were not close to winning with him. The question is whether he can be enough of a difference-maker in Chicago to justify the cost.

What the coverage missed

Barnwell’s analysis is thorough on the history and fair on the risk. What it does not dwell on is the pattern within the Bears’ own building. General manager Ryan Poles has been aggressive with in-season trades, and aggressiveness is a trait that compounds. Each deal that works encourages the next one. Each deal that does not work also encourages the next one, because the temptation to fix the mistake with another splash is strong.

The Mack trade is the closest analogue, and it happened to this same franchise. Mack was a better player than Simmons at the time of the deal, and he was traded to a worse team. The Bears went 12-4 in Mack’s first season and never won a playoff game with him. They traded him away for a second-round pick.

Simmons is 28 and entering his prime. He is under contract through 2026. The Bears are better positioned than the 2018 team was, with a franchise quarterback on a rookie deal and an offense that is already working. But two first-round picks is two first-round picks, and the players the Bears could have drafted with those selections are players they will never have.

What I think

The Bears should have made this trade. They have Caleb Williams on a rookie contract, which is the window where you can afford to spend draft capital on veterans. Simmons is a true interior disruptor, and the defense needed one. The alternative is drafting a defensive tackle in the first round and hoping he becomes Simmons, which most of them do not.

But Barnwell is right that the hit rate on these deals is not great, and the Bears know that better than anyone. The Mack trade did not bring a championship. The Simmons trade might not either. The difference is that the 2026 Bears are closer to a title than the 2018 team was, and Simmons fills a more specific need. If the Bears win a Super Bowl in the next two years, nobody will ask what they gave up. If they do not, the Titans will have two first-round picks and the Bears will have a defensive tackle and a lot of regret.