The Bears' Best and Worst Free Agent Signings in the Last Decade

The 2026 NFL free agency period is just days away, and the Chicago Bears suddenly find themselves in desperate need of help along the offensive line. We already knew that left tackle Ozzy Trapilo would miss most of the upcoming season, but the shocking Tuesday announcement that Pro Bowl centerDrew Dalman is retiring after just one season with the Bears changed everything.

We'll soon find out exactly how general manager Ryan Poles prioritizes the Bears' offensive line positions. But until the legal tampering window opens at noon EST on Monday, there's nothing we can do but speculate. How about instead we take a quick trip down memory lane and review the Bears' best and worst free agency signings of the last decade?

Sadly for Bears fans, picking just a handful of bad free agency swings as the worst was a tough call. As I looked back, I saw several signings that went badly. To make it easier, I only included a signing as one of the worst if their contract ran at least three years and included significant guarantees.

Best Signings

Allen Robinson - 2018

ARob signed a three-year, $42 million deal with the Bears ahead of the 2018 season and immediately rewarded them with 55 catches for 754 yards and four touchdowns. His next two seasons were even better, going for a combined 2,397 yards and 13 touchdowns in 2019 and 2020. No Bears receiver since then has recorded at least 1,000 yards in back-to-back seasons.

Cordarrelle Patterson - 2019

For just $10 million, Patterson brought the Bears the kind of exciting special teams weapon that hadn't been seen in Chicago since the days of Devin Hester. In 2019 and 2020, he averaged 30 yards per kick return and also posted two kick return touchdowns, but it was his habit of finding a cameraman after a win and yelling, "How 'bout them Bears?" before running into the tunnel that truly endeared him to the fanbase.

Andrew Billings - 2023

Usually, low-risk, high-reward deals don't work out, but Billings was such an immediate success for the Bears after signing a one-year, $2.75 million contract in 2023 that the Bears signed him to a two-year extension in November that same year. The Bears went from allowing 157 rush yards per game in 2022 (second-worst in the league), to leading the NFL by surrendering just 86.4 rushing yards per game in 2023, and that was thanks in large part to Billings' massive presence in the middle.

Kevin Byard III - 2024

We don't often see an aging veteran recapture his youth on a new team, but that's what the Bears got from Kevin Byard III after signing him to a two-year, $15 million contract in 2024. The veteran safety added a dependability factor to Chicago's somewhat fragile secondary, going two years without a single game missed. In 2025, he hauled in seven interceptions and was named a first-team All-Pro, his third such award.

Drew Dalman - 2025

Despite Drew Dalman's shocking retirement on Tuesday, I still feel obliged to include him as one of Chicago's best free agency signings of the past decade. The Bears had not had quality play from their center since Kyle Long's 2018 season at center, but Dalman came in from Atlanta and immediately stabilized the position, earning his first Pro Bowl nod in 2025. He looked like Chicago's next great center, but the Bears are once again left looking for a starter.

Worst Signings

Robert Quinn - 2020

Yes, Robert Quinn broke the Bears' franchise record for most sacks in a season with 18.5 in 2021, but he was virtually unplayable for the rest of his time in Chicago. Quinn signed a five-year, $70 million deal with the Bears in 2020, with $30 million guaranteed, but recorded only two sacks that season. In 2022, he had just one sack through seven games, at which point the Bears traded him to the Eagles.

The way things went with Quinn, I think most Bears fans would have preferred he had never broken the franchise sack record at all, which would have left it with a true Bears legend, Richard Dent.

Grady Jarrett - 2025

There's still time for Jarrett to turn things around in his stint with the Bears, but his 2025 season was awful. The Falcons unexpectedly released him hours before the legal tampering period opened up, and by that same afternoon, the Bears signed Jarrett to a three-year, $43.5 million deal, one that Jarrett did not live up to. His 56.7 PFF grade ranked 76th out of all defensive tackles, and he registered only three sacks and 21 total pressures.

Dayo Odeyingbo - 2025

The Bears' signing of Dayo Odeyingbo didn't make much sense to anyone at the time, and that three-year, $48 million contract only looks worse after his first season in Chicago. In eight games, before a season-ending injury, Odeyingbo put up just one sack and 10 total pressures. His 53.5 PFF grade landed him outside the Top 100 defensive ends.

Ironically, Odyeingbo's $32 million in guarantees is a big reason why Chicago's 2026 salary cap situation is so tricky. They need major help at defensive end, but they likely can't afford it because of their most recent defensive end signing.

Mike Glennon - 2017

Speaking of baffling free agency moves, signing Mike Glennon to a three-year, $42.5 million deal, with $18.5 million guaranteed, will forever be one of Chicago's worst attempts at finding a franchise quarterback. Everyone knew that the Bears would be selecting a quarterback in the 2017 NFL draft. If they only wanted Glennon as a mentor for their rookie, why sign him to what was such a large deal at the time?

In the end, Glennon started only four games for Chicago before they handed the keys to rookie Mitchell Trubisky. For those counting, that means he earned $4.625 million per game as a Bear, which would average out to over $78 million for a full 17-game season. Not a bad day's work if you can get it.

Mike Glennon and Mitch Trubisk — Patrick Gorski-Imagn Images

Nate Davis - 2023

We've finally arrived at the signing that was by far Ryan Poles' worst work, and arguably the worst work of any Bears general manager this decade. Poles had been warned not to sign Nate Davis by in-house coaching staff, according to the Chicago Tribune's Dan Wiederer. But Poles ignored the red flags and signed Davis to a three-year, $30 million deal with $19.25 million guaranteed.

The signing was an utter catastrophe from the start. Davis rarely practiced and showed almost no effort in games en route to an abysmal PFF grade of 48.0 for the 2023 season. In 2024, he started just two games before being benched for the next four games as a healthy scratch. Then, on November 13th, the Bears released their $30 million free agent acquisition. He has not played a snap of football for anyone since then.

We'll never know if Ryan Poles' job was in serious jeopardy during the 2024 season, but it sure felt like Davis would be the guy who would get him fired at the time.

Nate Davi — Mark J. Rebilas-Imagn Images

Best Signings

Worst Signings

Sign Up For the Bears Daily Digest - OnSI’s Free Chicago Bears Newsletter