General manager Ryan Poles' rebuild is set to enter its next phase in 2024, but critical moves over the next month will determine what the expectations should be in Year 3 for this regime.
The quarterback decision headlines the offseason, but the Bears have many boxes to check to go from a 7-10 team to a legitimate playoff and NFC North contender.
Poles has turned the roster over and built a solid foundation around star wide receiver DJ Moore, edge rusher Montez Sweat, linebacker Tremaine Edmunds, tight end Cole Kmet, and cornerback Jaylon Johnson.
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It's imperative that the Bears stack talent on talent this offseason, including filling key holes that held them back in 2023.
CHICAGO BEARS
Here's a nine-step plan for Poles and the Bears to follow this offseason to go from rebuilding darling to postseason threat:
1. Tag Jaylon Johnson and try to extend
The first box for the Bears to check is a relatively simple one.
The NFL franchise tag window opens Tuesday, and the Bears will likely place the tag on cornerback Jaylon Johnson as they continue to work toward a long-term deal.
Johnson bet on himself last season and finished with a Pro Bowl nod and second-team All-Pro selection. After the season, Johnson told Keyshawn Johnson that he wants to be the highest-paid cornerback in the NFL.
That is a sharp departure from Johnson's words before training camp when he admitted he didn't have the accolades or turnovers to be paid like Dallas Cowboys star Trevon Diggs.
The Bears and Johnson were far apart on negotiations midseason, leading to Johnson asking for and receiving permission to seek a trade. The Bears held onto Johnson, and Poles said it would have taken a first-round pick or high second to trade Johnson.
The two sides didn't restart negotiations during the season, but Poles said they hadn't even found the gap in their numbers before the trade request.
With Johnson's stance on his value changing, it's hard to imagine both sides have made significant headway over the past month. The Bears likely will place the tag on Johnson and then spend the next five months working with his camp on an extension ahead of the July deadline.
2. Trade Justin Fields for maximum return
With the No. 1 overall pick in their pocket and USC's Caleb Williams sitting there for the taking, the Bears finalize their plans to move on from Justin Fields at next week's NFL Scouting Combine.
Fields showed flashes of brilliance during his three years in Chicago, but the passing consistency never arrived in the way that was required for Poles to pass on Williams.
While Fields evolved as a passer this past season, he continued to struggle in winning time.
Out of 40 quarterbacks who threw at least 50 passes in the fourth quarter this season, Fields ranked 39th in passer rating at 53.4. Only Bailey Zappe was worse. He ranked 28th in yards, tied for 26th in touchdown passes, and was tied for the second most interceptions in the final quarter.
Thirty-one quarterbacks threw at least 20 passes this season while trailing with four minutes or less remaining in the game. Fields ranked 29th in passer rating and 28th in completion percentage and was tied with Jordan Love and Aidan O'Connell for the most interceptions.
In the end, Fields didn't do enough to remove all doubt that he is a franchise guy. The Bears love him as a person and believe in his potential.
But Williams' potentially generational ability and the chance to reset the quarterback contract clock are too important to pass up.
Once the Bears have fully locked in their decision to move on from Fields, they should trade him ahead of free agency. There are a few teams in quarterback purgatory that should be in the Fields market -- Steelers, Patriots, Falcons, Broncos -- but with veterans Kirk Cousins and Russell Wilson expected to be available in free agency (Cousins can be tagged), the Bears should try to move Fields before the quarterback carousel starts in order to obtain maximum return on the asset.
3. Draft Caleb Williams
Williams is going to be picked apart from now until draft day. It happens every cycle.
The 2022 Heisman Trophy winner has faults. No question. The hero ball he needed to play to win on a bad USC roster won't play in the NFL, and two years of being allowed to do that can lead to bad habits.
But Williams has elite arm talent, accuracy, and his off-script playmaking has drawn 4. to Patrick Mahomes. (Comps are not meant to predict what a player will become, only to add context to said ability.)
In two years at USC, Williams threw 72 touchdown passes and just 10 interceptions. His tape is littered with jaw-dropping throws from a series of different arm angles.
He has rare ability and an astronomically high ceiling.
Poles did well to turn the No. 1 pick in last year's draft into a gold mine. In drafting Williams, he gets to put the finishing touches on an all-time heist.
4. Add elite playmaker with second first-round pick
The Bears will have options when they go back on the clock at No. 9 overall.
Edge rusher is in play. The Bears could go left tackle depending on their evaluation of Braxton Jones' second season and how good Penn State's Olu Fashanu and Notre Dame's Joe Alt can be at the next level.
But the Bears would be wise to give Williams another weapon to pair with Moore.
Washington wide receiver Rome Odunze should be the leader in the clubhouse, but there's a good chance he's off the board before the ninth pick. LSU wide receiver Malik Nabers and Georgia tight end Brock Bowers would be a good Plan B if Odunze is off the board.
The Bears have a top-tier receiver in Moore and an ascending tight end in Kmet, but they should add as many weapons as possible around Williams to help the USC star settle in and start his NFL development off on the right foot.
If the Bears draft Williams at No. 1, everything else has to be about fostering an environment for growth and development. Adding Odunze, Bowers, or Nabers would give Williams three pass-catching weapons to work with in Year 1.
5. Sign C Connor Williams
The Bears need to solve their center issue this offseason.
They will have options in the draft with West Virginia's Zach Frazier, Oregon's Jackson Powers-Johnson, and Georgia's Sedrick Van Pran.
But the Bears might be better served addressing the pivot in free agency with 26-year-old Connor Williams.
Williams has been a top-10-graded center in each of the last three seasons, per Pro Football Focus. He's a tremendous run-blocker in a zone scheme and allowed only one sack and six pressures in 2023.
Williams did tear his ACL in Week 14, which could impact his market in free agency. The Bears should be able to land him on a deal that pays $6-8 million AAV, filling a position of need with a proven veteran on an affordable deal.
6. Sign A.J. Epenesa or Za'Darius Smith
There was a lot of talk in Las Vegas about the Bears being interested in signing Minnesota Vikings edge rusher Danielle Hunter or trying to trade for Philadelphia Eagles pass-rusher Haason Reddick if he asked for a trade.
Both would be tremendous additions opposite Montez Sweat, but the cap numbers are hard to fit.
After cutting Cody Whitehair and Eddie Jackson, the Bears have around $67 million in cap space. But when you take out around $13 million for the draft class, $7 million for in-season spending, and $18.8 million for Johnson's tag, the Bears are already under $30 million.
They have to be economical. Reddick has a $14.25 million base salary next season, and Hunter will likely fetch a deal with an AAV of around $20 million.
There is cap chicanery that can be done, but the Bears will likely have to build their edge depth on the middle rung of free agency.
Epensa, 25, had 29 pressures and seven sacks last season for the Bill. He has developed into a quality rotational edge rusher and still has room to grow. He would be an affordable option on a multi-year deal, paying about $7 million annually.
If the Bears want to swing a bit higher, I like Za'Darius Smith.
The 31-year-old had 60 pressures and six sacks playing opposite Myles Garrett last season. Smith outplayed his contract in 2023 but is on the tail end of his prime and is likely looking at a deal that pays in the $10-$13 million range.
Epensa feels like a more realistic option, but if the Bears can make the numbers work, I think Smith and Sweat would be a nightmare pairing for opposing offenses to face.
7. Extend, restructure DJ Moore's contract
Moore signed an affordable extension with the Carolina Panthers in 2018 that sees his base salary fall from $19.95 million in 2023 to $15.8 million in 2024 and $14.8 million in 2025.
In terms of base salary ($15.8 million), Moore is slated to be the 12th highest-paid receiver in 2024. If you factor in total cash ($16 million), he is set to rank 16th behind Christian Kirk.
Moore is coming off a career season where he racked up 1,364 yards and eight touchdowns.
With agent Drew Rosenhaus driving the bus, you can bet a reworked deal and an extension is coming Moore's way. The Bears would be wise to get that done before the price increases.
8. Draft Eddie Jackson's replacement
We've reached the small potatoes portion of the menu.
The Bears cut ties with veteran safety Eddie Jackson last Thursday.
Poles should try to find a long-term replacement for Jackson on Day 2 of the 2024 NFL Draft, with Georgia's Javon Bullard looking like the ideal fit alongside Jaquan Brisker.
9. Re-sign Darnell Mooney
Even if the Bears draft a receiver with their second first-round pick, they still will only have two wideouts they can rely on, with Tyler Scott and Velus Jones Jr. needing to show much more to elevate themselves into that category.
Say what you will about Mooney's struggles over the past two seasons, but the Bears have been adamant that the fault doesn't lie at the receiver's feet.
Mooney was a 1,000-yard receiver in the final season of Matt Nagy's tenure but never flashed as expected in Luke Getsy's system.
After a disappointing 2023 campaign, Mooney's value on the market is at an all-time low. I expect a contender to buy low on him, but if his market doesn't develop, the Bears should bring him back on a one-year deal as a reliable slot receiver for Williams.
The Bears respect Mooney's work ethic and believe in his talent. He has shown an ability to create separation consistently and is beloved in the locker room.