Ranking the Bears' 4 worst free agency signings of the last decade

Those that don't learn from the past are doomed to repeat it. We hope you're paying attention, Ryan Poles.
Nate Davis' time with the Bears didn't come close to panning out.
Nate Davis' time with the Bears didn't come close to panning out. | Justin Casterline/GettyImages

NFL free agency is only two weeks away, and teams are already maneuvering to chase their top targets. That includes the Chicago Bears, who recently released DeMarcus Walker and Gerald Everett to free up even more money to spend.

The Bears are now well-positioned with just under $75 million in cap space, but as we've seen in the past, cap space doesn't mean anything if it isn't used wisely. Even worse, signing the wrong players can set a team back for years, a fact that Bears fans know all too well. Just in the past decade, there are just as many examples of bad signings as there are of good ones, so general manager Ryan Poles needs to take what follows as a cautionary tale.

The mood is high in Chicago in the wake of signing Ben Johnson, but today we'll be shifting gears to focus instead on something a bit less positive — the four worst Bears free agent signings of the last 10 years. In looking back over every signing the Bears have made, what stands out is how conservative they've generally been. This has not been a franchise that's traditionally made a big splash in free agency, but there are still some examples of big deals gone wrong. Let's get into it.

4. Gerald Everett for two years and $12 million in 2024

The Bears cut Gerald Everett this past Friday. Coincidentally, the tight end had the same number of receptions last year as there are words in that first sentence. Eight. Eight whole catches for a total of 36 yards after signing a two-year, $12 million deal last offseason.

With Cole Kmet as the TE1 and three quality receivers ahead of him in the passing game pecking order, Everett was never going to catch 50 or more balls like he did each year with the Chargers, but he was definitely supposed to do more than that. If Ryan Poles wanted a veteran tight end to mentor his offense, Marcedes Lewis was already on the roster, and he's 10 years older and wiser than Everett.

Cutting Everett now saves the Bears about $5.5 million in cap space, but more than that, it's an admission that signing him was a mistake. Bears fans would rather that than doubling down on money spent poorly, but still, we'd like to see Poles make better decisions when free agency kicks off this year.

3. Trey Burton for four years and $32 million in 2018

Everett contributed next to nothing in Chicago, but he pales in comparison to fellow tight end Trey Burton. The answer to a good football trivia question (who threw the Philly Special to Nick Foles in the Super Bowl?), Burton was given one of the largest tight end contracts in league history by the Bears, who were desperate at the time to give Mitch Trubisky some promising options to throw to.

Burton was pretty solid in his first season, catching 54 balls for 569 yards and six touchdowns, all career highs. This was the last time the Bears won the NFC North, which Bears fans will also remember with absolute horror as the year that Cody Parkey double-doinked the Bears out of the playoffs.

That game came against Burton's former team, the Eagles, but Burton didn't play in the game for what, at the time, were mysterious reasons. Fans thought he quit on the team or was overcome with anxiety at the prospect of playing his old team. Those are strange assumptions to make, but understandable given that Burton wasn't thought to be in any danger of missing the game until he was added to the injury report the night before.

Whatever the reason, Burton wasn't there to help the Bears avoid the most painful loss in franchise history, and he did nothing to redeem himself the next season, only catching 14 balls in eight games. The Bears cut him after that second season, and he was out of the league just one year later, before his four-year contract was even supposed to end.

Before coming to the Bears, Burton had only caught 63 passes in four seasons with the Eagles. Former Bears general manager Ryan Pace really outsmarted himself by projecting that Burton could be a go-to receiving option without the past performance to back that up.

2. Nate Davis for three years and $30 million in 2023

Let's flash forward to more recent times for our next free agent bust. Ryan Poles has been criticized for not fixing the offensive line, but he did try when he signed Nate Davis away from the Tennessee Titans two years ago. Davis was a solid right guard for Tennessee, but he was anything but in Chicago. He struggled with run blocking, pass protection and staying healthy, and what's worse is that he was criticized for an apparent lack of work ethic, as he missed time on multiple occasions for unclear reasons.

The Bears offensive line was one of the most maligned units in the NFL last year. Caleb Williams played all season, somehow surviving being sacked 68 times, the third-most in NFL history. The line was riddled with injuries, often having to rely on multiple backups at once. It's quite a damning statement that given all that, the Bears still decided to release Davis before their Week 11 game against the Packers.

When Davis wasn't injured or feigning injury, he was a healthy scratch, as he was when the Bears traveled to London to play the Jaguars in October. All in all, he appeared in just 16 games, leaving the Bears right back where they started two years ago. If the offensive line is the biggest area of need the Bears have (and it is), Davis is the biggest reason why.

1. Mike Glennon for three years and $45 million in 2017

When the Bears signed Mike Glennon to be their new franchise quarterback, it was a move that made no sense at all in the moment. The former Virginia Tech Hokie had been Jameis Winston's backup with the Tampa Bay Bucs for two years, before which he backed up 35-year-old Josh McCown, who was deemed expendable by the Bears one year earlier.

Glennon was a former third-round pick with zero mobility and modest arm strength, but Ryan Pace signed him for three years and $45 million anyway. That in itself was confounding, but that mistake was compounded exponentially when a few months later, the Bears moved up to No. 2 in the draft to take Mitch Trubisky.

Poor Glennon was at the Bears' official draft party, making for an extremely awkward situation where the guy who was just signed to be the face of the franchise was ostensibly replaced before ever appearing in a game.

Glennon's fate was sealed on draft day, but then he was trotted out to start anyway so that Trubisky, who had only started one year in college, was given time to develop. That lasted all of four games, as the fans clamored for their new rookie after Glennon threw four touchdowns and five interceptions while leading the Bears to a 1-3 record.

Glennon played for four teams in the next four years, never winning another game as a starter.

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