Since Caleb Williams remains on a cheap rookie deal, the front office has room to spend big on the players who actually make the team win. The logic behind each move is sound as Sports Illustrated reports that four Bears secured contract extensions for 2027 and beyond. The team has proven it can find value, and now it must pay for it before the market does.
The most urgent case involves Theo Benedet. After losing the starting left tackle competition at camp, he assumed the position when Braxton Jones suffered a season-ending injury. He did not panic. Benedet has allowed only one sack and 18 pressures while maintaining a pass-blocking grade of 68.4 through nine games, according to reports. In the run game, he ranks 19th among tackles in the NFL with a 73.3 grade. Waiting is a poor strategy even though the Bears hold complete authority over him once he becomes an exclusive rights free agent following this season. A player who holds the line this well deserves a long-term deal as a potential swing tackle or starter.
Jackson’s Turnaround Demands Cash
Then there is Jonah Jackson, a story of redemption that the Bears must finish. After the team acquired him in a 2025 trade with the Rams, his career appeared finished because he missed most of that season due to injury. This season has been particularly impressive, with Jackson ranking fourth in run-blocking grade at 85.1 and fifth in overall grade at 83.1 among guards while not permitting a sack. Although he is under contract for another year, he has no guaranteed money left on his deal. That makes him a perfect candidate for a long-term extension. Locking him up now also lowers his $12.2 million cap hit for 2027.
Future Plans for D’Marco Jackson
The report also highlights linebacker D’Marco Jackson, who started his ascension last season as a pleasant surprise for Chicago. He is another player whose play has earned him a spot on the extension list. The team has the flexibility to keep these core pieces together while Caleb Williams matures. The Bears are 7-2 and sitting in first place in the NFC North, so keeping the offensive line solid is the smartest play they can make. Sports Illustrated reports that the team may allocate resources to players who have demonstrated their value while in Chicago. With a strong 7-2 record marking the midway point of the 2026 season, the Bears have landed their bye in an ideal spot to take stock of these performances.
