The Sun-Times’ Bears experts — Patrick Finley, Jason Lieser and Mark Potash — break down the Bears’ dynamic offseason to this point:

What can Caleb Williams show this offseason?

FINLEY: Confidence. A quarterback who carried himself as an iconoclast in college is inheriting one of the toughest jobs in American sports. Embracing his championship goals — and not being afraid to talk about them — is the best he can do until the snaps start counting in late July.

LIESER: For now, the Bears just need more of what they’ve already seen: poise and an eagerness to learn. Williams struck the ideal balance between confidence and humility in his arrival and needs to continue that once veterans arrive for Organized Team Activities and minicamp. He has to assert himself without alienating teammates. Because once training camp begins, the Bears are looking to him to lead.

POTASH: That he learns quickly. The Bears might not be in “playoffs or bust” mode in 2024, but they still need to hit the ground running in training camp. With every player adjusting to new coordinator Shane Waldron’s offense, it’s up to the quarterback to be a step ahead of everyone else. If Williams can master the basics quickly, the pieces are in place to avoid a familiar Bears lament: “We’re still in the first year of this offense.”

Which rookie not named Caleb Williams is the most compelling?

FINLEY: Receiver Rome Odunze would be the face of almost any other team’s draft class. He’s charming, sure — pass game coordinator Thomas Brown said he was his favorite interview of anyone outside the quarterback class — but also a player the Bears pegged as one of the biggest difference-makers in the draft. For a franchise that hasn’t drafted a standout receiver since Alshon Jeffrey in 2012, that’s plenty reason to be excited.

LIESER: Iowa punter Tory Taylor. It’s unusual to be so intrigued by a punter, but the Bears jumped at him in the fourth round. If he proves he was worth being drafted that high, it’ll actually be pretty interesting.

POTASH: Defensive end Austin Booker is young (21) and inexperienced (18 college games, one start), but at 6-6, 245 with long arms and a lean, athletic build, it’s easy to see why scouts would be intrigued by his pass rush ability. He likely needs time, but if Matt Eberflus’ defense takes the next step, Booker with his raw talent could find playmaking opportunities.

Which hole does general manager Ryan Poles still have to fill?

FINLEY: Rotational help at defensive tackle. Justin Jones wasn’t an advanced stats darling — Pro Football Focus rated him the league’s 107th best tackle last year —but that didn’t stop the Cardinals from signing him to a three-year, $31.2 million contract in March. Jones played 69% of the Bears’ defensive snaps last year; presuming Gervon Dexter and Zacch Pickens can take his place is an act of faith.

LIESER: The Bears’ pass rush is a glaring need, and it’s too late to do much about it personnel-wise. Poles’ best option probably is to re-sign defensive end Yannick Ngakoue, who had a career-low four sacks in 13 games last season but averaged 9.3 per season before that. He’s only 29 and if he’s fully recovered from a broken ankle, he’s a decent choice. It’s either that or bet on Booker developing into an immediate starter.

POTASH: After a 2022 teardown and 2023 first-step rebuild, Poles has acceptable pieces in place at virtually every position — unless defensive end DeMarcus Walker is no longer acceptable. What Poles needs is growth from within at several positions —Dexter, left tackle Braxton Jones, safety Jaquan Brisker, cornerbacks Tyrique Stevenson and Kyler Gordon. The biggest question mark might be at center, with Ryan Bates, Coleman Shelton and Doug Kramer.

What aspect of the Bears’ schedule release this week will you be watching?

FINLEY: Beside my own selfish interests — will they play on Christmas? — I want to know whether Eberflus plans to practice all week in England before playing there in mid-October. Matt Nagy went over late in 2019, the Bears lost to the Raiders and a franchise-altering slide began. Fun fact: Nagy was 15-5 before the London loss and 19-26 afterward.

LIESER: Their game against the Commanders and No. 2 pick Jayden Daniels. The Bears will visit them for the second season in a row, but this time the Williams-Daniels matchup makes it nationally relevant. This would be an excellent choice as a prime-time game for the season opener.

POTASH: Their second-half schedule. With a rookie quarterback and a first-year coordinator, the Bears figure to be better in the second half than the first. They probably would be better off playing their apparent toughest games — at the 49ers, at the Packers, at the Texans — in the second half.

What’s Matt Eberflus’ biggest challenge?

FINLEY: Dealing with expectations. The buzz surrounding the Bears is new territory for the head coach, whose team was widely expected to stink in both 2022 and 2023. He’s now coaching the most famous athlete in Chicago — one who’s yet to play a game. The Bears could very well be talk of the NFL; by speaking publicly more often than anyone in the franchise, Eberflus will be their face.

LIESER: Balancing the dual roles of defensive play caller and head coach. He said from the start he did not want to do both jobs and thought the most prudent approach was to be a CEO-style head coach. He hired defensive coordinator Eric Washington, but will keep calling plays because it went so well last season when he stepped in for Alan Williams. But his job security hinges on Williams’ progress more than anything else.

POTASH: Keeping his defense on upward path it was in the second half of last season. If the offense is a work-in-progress with a rookie quarterback and first-year coordinator, that wouldn’t be a big surprise. The defense being the culprit for a disappointing season would be far more damaging to Eberflus’ long-term future with the Bears.

Grade the Bears’ offseason.

FINLEY: A-. It’s hard to ask them to do more, starting with assembling a proven, dynamic offensive coaching staff in January and riding the momentum of the No. 1 overall pick all the way to the draft. I’d give them an A+ had the downtown stadium pitch been met with a warmer reception.

LIESER: A. Williams’ arrival is invigorating. Some of their other moves, on both the roster and coaching staff, are debatable, but Williams outweighs them all. If he’s as great as the Bears anticipate he’ll be, he’ll change everything.

POTASH: A. By trading for Keenan Allen and drafting Williams and Odunze, Poles has given the Bears their best chance in years to solve the chronic offensive issues that have dogged the franchise.

Patrick Finley

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