Wednesday, December 31, 2025

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The Chicago Bears 2019 Offseason: How To Kill A Contender

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When the 2018 season concluded for the Chicago Bears, optimism was high. The team had won the NFC North division at 12-4 and came a missed field goal away from knocking off the defending Super Bowl champions. Expectations were understandably high going into 2019. They had a top 5 defense, and an offense sprinkled with talented pieces. All GM Ryan Pace and head coach Matt Nagy had to do was not mess it up.

Instead, they did the equivalent of peeing in the punch bowl. Nobody wanted to admit it at the time, but what those two did the following offseason was the single most impressive bit of self-sabotage witnessed in the past decade. Every decision they made somehow turned out to be the wrong one and laid the groundwork for the Bears’ collapse from emerging contenders to rebuilding a few years later.

Here’s how they did it.

Chicago Bears ruined a good thing in every way.

Let Adrian Amos walk in free agency.

It was understood why the Bears made this decision at the time. Eddie Jackson had just made All-Pro the previous year and was lining himself up for a massive payday. Pace didn’t subscribe to the idea of paying two safeties big money. Business-wise, it was logical. It was also wrong. Amos did so much for the secondary since his arrival in 2015, including the ability to handle box duties and allowing Jackson to roam free in coverage. It should’ve been a red flag when the Green Bay Packers quickly signed him.

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Sure enough, he’s been excellent for them in the three seasons since. Fittingly his first interception with them came in the 2019 season opener at Soldier Field. An omen of things to come. Jackson, meanwhile, got his payday and hasn’t been the same since.

Subbed Rashaad Coward for Bryan Witzmann

People forget the Chicago Bears offensive line in 2018 was actually solid. They protected Mitch Trubisky well and did a good enough job on the ground. One of the unsung heroes of that run was veteran Bryan Witzmann, who allowed only 16 pressures in 306 pass-blocking snaps at right guard. Rather than keep him around for cheap, Nagy opted to go with Coward, a converted defensive lineman with minimal experience. The results were catastrophic as Coward became the weak link of a line that regressed in every facet that year.

Switched Cody Whitehair and James Daniels.

One thing that became true about Nagy throughout his coaching tenure was his terrible tendency to mess with a formula, even if it was working. As stated above, the Bears’ offensive line was good the year prior. Trubisky was sacked only 24 times. Yet they decided to change things up for whatever reason, shifting Whitehair from his customary spot at center to left guard and Daniels from left guard to center.

The thinking was Chicago had always intended to make Daniels their long-term center when they drafted him. While that may have been true, the reality is the guy had been terrific as a rookie at left guard. It made little sense to move him from a position he played well only because that wasn’t part of the plan. Eight games later, the experiment ended after the second-year man struggled. Both were switched back to their original spots but not in time to rescue the offense.

Traded Jordan Howard

After a sluggish start to 2018, Howard once again showed why he was the engine that drove the Bears’ offense. He finished with 935 yards and nine touchdowns. Four of those came in the final three games of the season. Everything clicked when Howard was a focal point of the offense. Then a few months later, he was traded to Philadelphia for a future 6th round pick. Just like that, the heart and soul of the offense was gone, all because he didn’t fit the scheme Nagy wanted to run. That was the first warning sign the head coach may not have the offensive acumen or flexibility he claimed to.

Traded up for David Montgomery

Let’s make this clear. Montgomery is a good player. This isn’t an indictment of him. This is about the entire process that led to his acquisition. Not only did the Bears trade a perfectly capable running back in Howard, they then compounded that mistake by trading up in the 3rd round of the draft to acquire Montgomery. They sent 4th and 5th round picks to New England for a 6th in return.

Think about this. If the Bears had kept Howard, those picks could’ve landed them names like Darius Slayton, Cole Holcomb, Gabriel Davis, or L’Darius Sneed. Not to mention they would’ve had Dawson Knox or Maxx Crosby still on the board with that original 3rd rounder. They got a minor upgrade at running back at the cost of two valuable draft picks. The further away one gets from that offseason, the more one must wonder.

How did that team not decline faster than they did?

The rest of the 2019 draft

Pace gets plenty of love for his success in the later rounds of a draft. Much of that praise is deserved. However, he picked a bad time to strike out. After grabbing Montgomery, he had only four picks remaining. They went as follows.

  • Riley Ridley – Off the team after three years
  • Duke Shelley – Below average backup
  • Kerrith Whyte – Cut after first preseason
  • Stephen Denmark – Cut after first preseason

All four picks did nothing for the Chicago Bears’ prospects in 2019 or any year after that. Montgomery was the only good pick they made, and he was an expensive one to acquire. If anybody wants to look at a sequence of events that began the downfall of the Nagy-Pace regime, all they have to do is point at the two months they spent ruining a good team that year.

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