Forgive me for sounding like a broken record, but the Chicago Bears are entering one of the most crucial off-seasons in franchise history this spring, as they begin their search for a new head coach — their sixth since Lovie Smith was fired following a ten-win season in 2012 — and attempt to build a roster that is ready to compete right away while 2024 1st overall pick Caleb Williams is still on a rookie contract. This process will begin not with the NFL Draft in April, but with free agency in March.

While it's expected that the Bears will select either an offensive tackle — Texas' Kelvin Banks Jr., LSU's Will Campbell, Ohio State's Josh Simmons — or an edge rusher — Georgia's Mykel Williams, Penn State's Abdul Carter, Texas A&M's Nic Scourton — with the 10th overall pick, that could largely depend on what they accomplish in free agency. With somewhere in the neighborhood of $83 million available to spend, the Bears are projected to have the 5th-most cap space in the league this spring, according to Spotrac.

So with all of that said, here are six free agents that Bears general manager Ryan Poles should be targeting as the offseason quickly approaches.

Trey Smith, Guard 

Kansas City Chiefs guard Trey Smith (65) leaves the field after warm ups before a game against the Buffalo Bills at Highmark Stadium.
© Mark Konezny-Imagn Images

If you're talking about the needs of the Chicago Bears, you need to start with the offensive line. Caleb Williams was sacked 68 times, the most in the league and the third-most in a single season in NFL history, and yes, some of this has to do with Williams holding onto the ball for longer than you'd hope, but more of the blame deserves to be placed on the shortcomings of a group that featured more combinations of players than any other unit in the league.

Second-year tackle Darnell Wright is the only starter along the offensive line who will definitely be back next season. Teven Jenkins is a free agent and there's skepticism that the Bears will bring him back. When Jenkins has been on the field he's played at the level of a starting guard, but he's missed 23 games in his four NFL seasons. He did play a career-high 14 games in the 2024 season, but there are still questions as to whether that's sustainable.

The rest of the interior offensive line features no players worth building around, so that opens the door for Kansas City Chiefs guard Trey Smith to come into the picture. Smith is fresh off of his first Pro Bowl season, but has been a rock on the Chiefs offensive line since being selected in the 6th round of the 2021 NFL Draft. He's only missed one game, and started all 67 that he's played in. He ended the 2024 season as the 10th-highest graded guard in the league, per Pro Football Focus.

Assuming the Chiefs aren't ready to shell out the money that Smith can command elsewhere — and that they don't use the franchise tag on him — it opens the door for Chicago to swoop in and sign the Pro Bowler. Given that Ryan Poles was in Kansas City's front office when the Chiefs selected Smith in 2021, there could be a prior relationship between the two that could play to Chicago's advantage.

Drew Dalman, Center 

Like Trey Smith, Falcons center Drew Dalman was one of the top-graded players at his position last season according to Pro Football Focus, but unlike Smith, the 26-year-old hasn't been on the field as consistently as you'd hope. Dalman missed eight games in 2024 thanks to an ankle injury, but that doesn't change his standing as the best center available in the free agency class of 2025.

Shoring up this position with Dalman and not having to shuffle through the likes of Coleman Shelton and Ryan Bates would be a huge step forward for the Bears.

Ronnie Stanley, Offensive Tackle 

Braxton Jones has been the starter at left tackle since he was selected in the 5th round of the 2022 NFL Draft, but for the sake of Caleb Williams' physical well-being, that needs to change. And the change can't come in the form of Kiran Amegadjie, who already looks like a swing and a miss of a 3rd round pick from last season.

Enter Ronnie Stanley, a solid, albeit relatively unspectacular option to protect Caleb Williams' blindside. Stanley is on the older side — he'll be 31 in March — but he started all 17 games for the Baltimore Ravens this past season, and would immediately give a boost to an offensive line that is in desperate need of consistency.

My guess is, depending on how the Bears believe the first nine picks of the 2025 NFL Draft will play out, they probably won't pursue a big money offensive tackle. But if the price is right, or if Ravens offensive coordinator Todd Monken ends up being the next head coach of the Chicago Bears, Stanley could be worth a long look.

Khalil Mack, Edge 

Las Vegas Raiders quarterback Aidan O'Connell (12) carries the ball against Los Angeles Chargers linebacker Khalil Mack (52) in the second half at Allegiant Stadium.
© Kirby Lee-Imagn Images

Turning to the other side of the ball, how about Ryan Poles facilitates a reunion between the Bears and Khalil Mack, since it was Poles who facilitated sending Mack out shortly after he took over as Bears general manager in 2022?

Despite the fact that Mack will be 34 at the start of the 2025 season, the veteran edge rusher has proven he has plenty of juice left. Mack has made three consecutive Pro Bowls since the Bears traded him to Los Angeles, and he's only a year removed from a 17-sack campaign, a career-high total for the future Hall of Famer.

Chase Young, Edge 

The Bears have been linked to Chase Young on numerous occasions in the past, including as recently as one year ago, when there was a belief that Young could end up signing with Chicago in free agency. The hope was that pairing Young with former Commanders teammate Montez Sweat would bring out the best in both players, but in the end, Young signed a one-year deal with the New Orleans Saints and the Bears have yet to find a consistent pass-rusher on the opposite side of Sweat.

Even though Young has failed to live up to the promise he flashed during his first season in Washington, it's still possible that the 25-year-old still has his best football in front of him.

Jevon Holland, Safety 

Miami Dolphins safety Jevon Holland (8) enters the field before the game against the Arizona Cardinals at Hard Rock Stadium.
© Sam Navarro-Imagn Images

Jaquan Brisker has one starting safety spot locked down, and Kevin Byard performed reasonably well during his first season in Chicago. It's possible that the Bears will ride out the 2025 season with the two of them, but there is another option… Byard has just one year left on his contract, and the Bears could save $7 million by releasing the 31-year-old before free agency begins. If that's what Ryan Poles decides to do, Jevon Holland could be the right guy to fill that opening.