Come next Monday, teams can begin discussing contract terms with free agents. That legal tampering period leads to the start of the new league year on March 18, when free-agent deals and trades can become official at 3 p.m. CT.
So begins a fascinating offseason for the Bears. Let's break down what awaits them.
The Bears have $24.5 million in salary cap space, according to Spotrac. That figure could increase, as it's based on the current collective bargaining agreement, which expires after the 2020 season.
The NFL players' association is set to vote this week on a new proposed collective bargaining agreement that has already been passed by the owners. If ratified, the new CBA would increase the salary cap for this offseason just days before the legal tampering period begins.
If the players' union approves the CBA, every team would have greater financial flexibility ahead of free agency. For Pace and his cash-strapped Bears, that could be significant.
The Bears rank 24th in available cap space, according to Spotrac. Their $24.5 million figure is more than $20 million below the league average mark. While lead negotiator Joey Laine can restructure existing contracts, the Bears are unlikely to be near the league average come next Monday.
General manager Ryan Pace's trade up to select Trubisky on draft night in 2017 was and is the biggest gamble of his tenure in Chicago, but his job security isn't necessarily tied to Trubisky.
Bears chairman George McCaskey offered Pace support after a disappointing setback season in 2019. Pace is now free to cut ties with Trubisky whenever he sees fit, which is why the Bears are building contingency plans at quarterback.
While the Bears' best-case scenario would be Trubisky responding well in 2020 and earning a contract extension, they're also planning for the likelihood that doesn't occur.
The Bears could explore veteran competition in the form of Teddy Bridgewater, Case Keenum or Marcus Mariota. Mariota being represented by the same agency as Trubisky could be a slight hindrance to the Bears' pursuit of him but not a complete non-starter, a source said.
A trade is also possible for the Bears, who could find a partner in the Bengals, who are open to moving Andy Dalton as they're expected to draft LSU quarterback Joe Burrow at No. 1 overall. Dalton is due $17.5 million in 2020, the final year of his current deal. Chicago could trade a player to Cincinnati to help offset the cost.
The Raiders may be motivated to trade starter Derek Carr this offseason. His availability is likely to be determined by interest in Las Vegas from big-ticket quarterbacks like Tom Brady or Philip Rivers. Carr, 28, is due just south of $20 million over each of the next three seasons.
Where the Bears stand with Trubisky and the quarterback position will become clear next week as they're forced to reveal their hand.
The Bears used six players at tight end last season and came away with no answers. It's why the position is an obvious need.
"I don't think that's a secret," Pace said in February.
There's obvious appeal to adding a free-agent tight end like Austin Hooper or Eric Ebron, but neither seems likely for the Bears given their expected cost.
The Bears signed Demetrius Harris, a fit for the Y tight end spot, after he was released by the Browns recently. His addition could mark the end of Adam Shaheen's tenure in Chicago at some point before the regular season starts.
The Bears' offensive line struggles in 2019 could largely be traced to their void at right guard. They never properly replaced Kyle Long when he was shut down in October, and that had a trickle-down effect.
In need of stability, the Bears would be best suited by adding an experienced veteran at right guard to complement their other four starters up front.
The Bears don't have to pursue a top guard like Brandon Scherff to shore up their offensive line. The solution may simply be a reliable veteran to help fix a sum-of-all-the-parts problem.
Graham Glasgow, an Aurora native who spent his first four NFL seasons with the Lions, would represent a major upgrade at guard. He's 28 and could fill that position for a number of years. Another option would be reuniting with 31-year-old Eric Kush, who started 11 games during a three-year stint in Chicago from 2016-'18.
By signing a low-cost veteran at guard, the Bears could also focus on developing Alex Bars and Rashaad Coward as potential long-term fits.
The Bears' most pressing focus in free agency outside of quarterback comes at inside linebacker, where a key decision is looming.
Kwiatkoski proved his place in 2019, posting career-best numbers with 76 tackles, three sacks and an interception while playing in all 16 games and making eight starts. He displayed improvement in coverage, which wasn't a strength in his first three seasons with the Bears.
Trevathan has been viewed as a rock on the Bears' defense and is one of the team's most influential leaders, but he remains the alternative to Kwiatkoski.
The Bears' two-year experiment with Aaron Lynch also brought mixed results, including frustration from his seven penalties in the neutral zone last season.
Pace has never been shy in making aggressive moves at outside linebacker, understanding well what the position means to the team's defense. Chicago has just three outside linebackers under contract for 2020 in Mack, Floyd and Devante Bond. The position could be addressed in both free agency and the draft.
With a number of quality veteran alternatives set to be available in free agency, look for the Bears to add an outside linebacker in free agency.
It's possible Pace could covet a premier player like Dante Fowler Jr., whom he scouted heavily ahead of the 2015 draft, but he'll command the type of contract that would limit what the Bears could offer a quarterback and Kwiatkoski.
Mario Addison, 32, could make more sense. He posted 30 sacks for the Panthers across the past four seasons.
The Bears can return their defense to its 2018 level of dominance. But they must fill two key voids in the secondary this offseason.
Cornerback Prince Amukamara was released in February in a move that opened $9 million more in cap space. The Bears are comfortable with their internal options at cornerback, Pace said, which include Kevin Toliver and recently signed Canadian Football League star Tre Roberson. Beyond them, the Bears are likely to pursue low-cost veteran competition for the spot opposite Kyle Fuller.
The Bears aren't expected to retain safety Ha Ha Clinton-Dix, who should command a bigger deal elsewhere than what Chicago is willing to offer. The Bears would also be wise to sign a true strong safety to allow Eddie Jackson to play his more natural position in coverage. The rotation between Jackson and Clinton-Dix playing in the box in 2019 limited Jackson's effectiveness in coverage.
The Bears could replace Clinton-Dix internally by retaining Deon Bush, whom they've developed over the last four seasons. Bush represents a natural complement to Jackson and has upside beyond his previous place in a backup role.