The Chicago Bears appear to have cemented themselves as one of the NFC's top expected contenders heading into training camp and the 2026 regular season. This is reflected by a schedule with no shortage of featured matchups and league-wide hype around Caleb Williams and head coach Ben Johnson. Still, there are a handful of questions and concerns around the team's current lineup as we finish out the final offseason stretch.
Four players stand out as facing difficult situations or mounting expectations based on offseason moves. With this in mind, let's look at four Chicago players clearly under pressure when training camp kicks off and the 2026 season finally begins.
1. Kalif Raymond
The veteran receiver was first signed as a clear starting option after the departures of DJ Moore and Olamide Zaccheaus. Drafting Zavion Thomas changed this, with the pass catcher now being forced to fight for his starting role. Raymond is going to be a returning option and weapon for Ben Johnson's offense no matter how the next month plays out. Still, there is no denying that his starting job is on the line with the pressure dialed up.
Raymond is an experienced pass catcher but lacks the potential upside of Thomas. It is notable that the two players were working together throughout minicamp despite being clear competition for the same spot. This is great for roster chemistry but leaves the veteran in a questionable position.
2. Grady Jarrett
The veteran would've been an offseason cut if not for his contract making it more affordable to remain rostered. Everything about Jarrett's 2025 season remains a source of frustration, with consistent injuries and a lack of expected production. Now, the Bears are facing an obvious level of expectations and have every reason to lessen Jarrett's role on the defense if it appears that the 2026 season is going to be a repeat.
Jarrett cannot afford a slow start to the year, needing to help set the tone on the inside. Everything about the veteran's career suggests that last season is the outlier, with the obvious exception being Father Time having caught up to the physical defender a bit early.
3. Austin Booker
Booker is being asked to take a major leap and become a primary edge-rushing source for the Bears. After offering 1.5 sacks in his rookie season, the defender jumped to 4.5 sacks in the 2025 season and showed signs of being a viable featured option. Now, the offseason has dialed this up from a possibility to an expectation as Chicago opted not to add a proven option at the position behind Montez Sweat.
The Bears badly need Booker to take the expected leap and prove that the offseason trust in the current pass rushing options wasn't misplaced. For Booker, this creates an obvious level of pressure and expectations that will start with fans paying close attention to his performance from the start of training camp and leading into the regular season.
4. Cole Kmet
Kmet is coming off a down year by his standards and watched as Chicago added to his position in the draft yet again. While Sam Roush might not be the dominating presence that Colston Loveland has proven to be, the depth is still noteworthy in the fact the Bears are preparing for life after Kmet does eventually leave the franchise. Struggles in camp could fast forward this with Kmet needing a strong performance to hold off Roush and bounce back after last year's regression.
Chicago already lost DJ Moore in the 2026 offseason making it more likely Kmet is rostered for at least another season. Still, his future remains far from locked leaving a consistent level of pressure and questions around the tight end's future.
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