5 best free agency signings in Chicago Bears’ history feat Julius Peppers, Thomas Jones, and more

The Chicago Bears are currently aiming to break their four-season playoff drought. The Bears blew hot and cold in the 2024 regular season but ultimately tapered off as the season reached its business end.

Hence, acing the offseason will be key to the Bears having realistic hopes at making the playoffs. It all starts with making savvy moves via free agency.

With that in mind, let's look at the five best free agency signings in Bears' history.

Five best free agency signings in Chicago Bears’ history

5. Martellus Bennett, Tight End - 2013

Martellus Bennett started his professional football career with the Dallas Cowboys. The versatile tight end thrived in Dallas and with the New York Giants before he joined the Chicago Bears for the 2013 season.

Bennett became an instant starter for the Bears and enjoyed three impressive seasons in Chicago. Bennett earned his sole Pro Bowl nod as a member of the Bears, and contributed to some highlight reel worthy plays for the NFC side. He later joined the New England Patriots for the 2016 season and won a Super Bowl at the end of the campaign.

4. Akiem Hicks, Defensive End - 2016

Akiem Hicks started his professional football career with the New Orleans Saints. He spent three full seasons with the Saints before being traded to the Patriots in 2015.

Rather than sign an extension in New England, Hicks opted to join the Chicago Bears via free agency. He went on to enjoy six impressive seasons with the Bears guiding the franchise to two postseason berths in his stint. He earned his sole Pro Bowl nod as part of the Bears in 2018, and is one of the 100 greatest Bears of All-Time.

3. Thomas Jones, Running Back - 2004

Newbies might know Thomas Jones for his acting roles in Luke Cage and Straight Outta Compton. However, before he became a thespian, Jones was a pretty good running back in the NFL.

Jones played for the Arizona Cardinals and Tampa Bay Buccaneers before he joined the Chicago Bears. He spent three seasons with the Bears and became the team's primary offensive weapon.

Jones amassed over 1,000 rushing yards in his final two seasons in Chicago. He proved to the rest of the league that he's one of the smoothest operators at the position, and spent five more years as a starter following his departure from Chicago.

2. Tim Jennings, Cornerback - 2010

Tim Jennings started his career as a ball hawk with the Indianapolis Colts. However, he left in 2010 to join the Chicago Bears via free agency.

The move turned out to be a brilliant one for both parties. The Bears added a lockdown CB to their defense, while Jennings played arguably the best football of his career in Chicago.

Jennings earned both his Pro Bowl nods as a Bear before he spent his final season as a pro with the Tampa Bay Buccaneers in 2015.

1. Julius Peppers, Defensive End - 2010

Julius Peppers is better known for his time with the Carolina Panthers. However, Peppers enjoyed an impressive stint with the Chicago Bears following his initial departure from Carolina.

Peppers was a tenacious quarterback chaser during his time with the Bears, and he was still comfortably one of the best at his position.

He earned one first-team All-Pro nod, a second-team All-Pro selection, and two Pro Bowls as a member of the Bears. His signing was a brilliant one by the Chicago front office as it impacted the locker room, and signaled intent to be a contender.