The Bears Got It Right With Eddie Jackson … So Who Else Deserves an Extension?

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The Bears Got It Right With Eddie Jackson … So Who Else Deserves an Extension?

Chicago Bears

There are times when big-money extensions can be tough to swallow, but I don’t think Eddie Jackson’s will be one of them.

Not with his skill set, age, projection, and general desire for more. And in a conference call after signing his new deal, Jackson expressed his desire to get something money can’t buy.

“There’s still a lot of unfinished business out there. The most important part is bringing that Super Bowl trophy back to Chicago,” Jackson said, via the Bears’ official website. “I’m not going to stop until I can’t go no more. That’s the one thing they’ll get from me. I want to retire a Chicago Bear and I want to do that after I help bring the Super Bowl to the city.”

I am 100 percent here for the Eddie Jackson Unfinished Business Tour in 2020.

Jackson is the type of prospect general managers dream about. He entered the 2017 Draft as one of its top playmaking safeties; someone who could line up at any number of places on the field and change the game no matter where he was lined up. And he certainly would’ve gone off the board earlier than he did, had it not been for a broken leg that ended early his final season at Alabama. Lucky for the Bears, I guess, who rolled the dice on Jackson with their fourth-round pick, only to see him shake the injury bug and flourish into one of the league’s top defensive backs.

Put simply: Jackson’s rise to stardom is THE single greatest draft story of the Ryan Pace era with the Bears – outcomes like that are just too few and far between. But he probably won’t be the last Bears standout that Pace tries to extend this offseason. So let’s explore some other possibilities.


The most obvious (and worthy) candidate for an extension is wide receiver Allen Robinson, who expressed a desire to stay in Chicago late in the season.

Robinson led the Bears in catches (98), receiving yards (1,147), and touchdowns (7). Not bad for a guy whose quarterback’s most consistent trait is inconsistency. The Bears don’t have a lengthy history of successful receivers, so letting Robinson go would be a real shame. Robinson isn’t a free agent until after the 2020 season, but handing over an extension now could lower his cap number for the 2020 campaign and give the team the necessary wiggle room to go out and improve the roster around him.


One of the sure signs of a healthy organization is when it extends its own draft picks. Bonus points (in a figurative sense) go to teams who turn middle-round picks into long-term contributors.

Perhaps linebacker Nick Kwiatkoski could join Jackson in being the next fourth-rounder to ink a long-term deal to stay in Chicago. The Bears have a need at starting inside linebacker next to Roquan Smith, and Kwiatkoski filled in admirably for Danny Trevathan when he went on injured reserve. Teaming Kwiatkoski and Smith could prove to be something that fortifies the middle of the defense.

Then again, the same could be said for Danny Trevathan. The Smith-Trevathan tag team was impactful in the middle when both were healthy this season. Unfortunately, both players finished the year on IR. Trevathan arrived in Chicago shortly after John Fox came to town and proved to be a culture-changing player who lifted those around him. I suppose the knock on Trevathan is that he played just one full healthy season in his four years with the Bears. But entering his age 30 season, Trevathan still looks to have a lot left in the tank when he is on the field. Even so, the Bears have yet another option who could be lined up for an extension.

Kevin Pierre-Louis flashed when he received some late-season burn after Roquan Smith’s season ended with a stint on IR because of a pectoral injury. I wouldn’t go as far to say the defense didn’t skip a beat with Pierre-Louis filling in for Smith, but his speed, instincts, and ability showed themselves often enough to put him into consideration as a starter in 2020. Save for his gaffes on special teams that occurred while running into punters, Pierre-Louis stood out for all the right reasons in 2020.

So maybe there is a cost-efficient middle ground that could be found between the Bears and one of their linebackers before they hit free agency. If so, great. If not, at least the Bears have options.


The most challenging extension conversation would come if Pace were to talk with Ha Ha Clinton-Dix‘s representatives.

After seeing his teammate and long-time friend get paid, it would be natural for Clinton-Dix to want to cash in on a big pay day of his own. Clinton-Dix missed out on that opportunity last year, but is better positioned to get a long-term deal this offseason because the market place figures to be less crowded at the high end.

In short, Clinton-Dix is going to want more than another one-year “prove it” deal, and I’m certain the Bears aren’t the best fit to give him the long-term deal he has earned with his play. And since Clinton-Dix and Jackson essentially play the same position, I would argue the Bears are better off allowing Clinton-Dix to walk, move Jackson back to a full-time free safety, then figure out who to pair him with in the draft or via another prove it deal via free agency.


The Bears missed Akiem Hicks’ presence on the defensive line last season, but Nick Williams did his best to try to soften the blow.

Williams set a career high with six sacks and five tackles-for-loss. Players who break out in their seventh year in the pros don’t tend to get big-money deals, but Williams should get a sizable raise from what he received last year. At minimum, the guy sounds ready to play the free agent market:

Williams expressed a desire to stay in Chicago, and I can understand why. Playing along side Khalil Mack, Akiem Hicks, and Eddie Goldman in the front seven seems like a grand-ole time. But the siren song of free agency can be tough to turn down.


Tarik Cohen has established himself as one of the league’s better return specialists, but his production as an offensive asset took a step back in 2019. Matt Nagy and the Bears’ offensive coaches have to go back to the drawing board in order to find how to best utilize Cohen in the offense. If they do, then a modest extension for a player who was believed to have Darren Sproles type potential could be in order.


Mitch Trubisky’s inadequate play on what was believed to be a Super Bowl contender in 2019 put an end to the idea of extending him on ice.

Author: Luis Medina

Luis Medina is a Writer at Bleacher Nation, and you can find him on Twitter at@lcm1986.