5 biggest contracts Chicago Bears have ever handed out

The Bears haven't always spent big, but things have changed over the years.
Chicago Bears, Montez Sweat
Chicago Bears, Montez Sweat / Todd Rosenberg/GettyImages

The Chicago Bears have had a history of being one of the cheaper franchises over the years. Fans had long loathed the team for failing to pony up and break out the check book when it comes to big name players.

But, over the course of the last 10-15 years, Chicago has changed its tune a bit. The Bears finally started to pay significant money for the more talented players around the league, whether they came from within the organization or as an offseason move.

The 2023 season and 2024 offseason have seen the Bears make some notable contract decisions with a couple of their own players, most recently coming when Chicago agreed to a new deal with cornerback Jaylon Johnson.

Where does Johnson's new deal rank among all-time Bears contracts? Let's take a look at the top five richest deals the Bears have ever handed out.

1. Khalil Mack
6 years, $141 million ($90 million guaranteed)
Signed September of 2018

2. Jay Cutler
7 years, $126.7 million ($54 million guaranteed)
Signed January of 2014

3. Montez Sweat
4 years, $98 million ($62.8 million guaranteed)
Signed November of 2023

4. Julius Peppers
6 years, $84 million ($42 million guaranteed)
Signed March of 2010

5. Jaylon Johnson
4 years, $76 million ($51.4 million guaranteed)
Signed May of 2024

Which Bears players have made the most money, annually?

It sure is saying something that two of the top five richest contracts in Bears history have been signed within the past year or so, and each have come on the defensive side of the ball. For now, both Johnson and Montez Sweat also make the list of the team's top-five paid players on an annual basis:


Average Annual Salary

1. Montez Sweat

$24.5 million

2. Khalil Mack

$23.5 million

3. DJ Moore

$20 million

4. Jaylon Johnson

$19 milliion

5. Jay Cutler

$18.1 million

For what it's worth, linebacker Tremaine Edmunds' deal pays him an average annual salary of $18 million, so he checks in just below Cutler on the above list.

Isn't it fitting that the number five player on the above list is a quarterback Jay Cutler? Sooner or later, another quarterback is going to bump him off that list -- a guy by the name of Caleb Williams, once he is up for an extension.