Jon Gruden hasn’t gotten back into coaching since his abrupt exit from the Las Vegas Raiders. Still, the former Super Bowl champion has stayed close to the game in other ways. Most recently, he was hired by Barstool as one of their most credible football experts. His work evaluating film remains one of the biggest reasons he is still a media draw. That is why the Barstool team often goes to him with tougher questions. Their most recent was an interesting one. Who is the biggest sleeper for the Super Bowl in 2027?

His answer was certainly a surprise. Gruden picked the Chicago Bears. It sparked immediate reactions among the group, most hovering between disbelief and outrage.

It isn’t really surprising. Most sports fans outside of Chicago view the Bears as a farce. Their playoff run in 2025 was largely thanks to an incredible series of 4th quarter comebacks and leading the league in takeaways. Those two things are never sustainable in the NFL. Reality will reassert itself this season. Super Bowl? Please. They’ll be lucky to make the playoffs.

Jon Gruden can see what the Bears are doing.

That is the same treatment they got last year. Nobody will treat you like a winner unless you do it again. Everybody can put together a surprise run once in a while. Sustaining success is the real challenge. One must not forget what the Bears lost this offseason. Kevin Byard and Nahshon Wright, who accounted for 12 of the team’s interceptions last season, left for the AFC East. D.J. Moore, their playoff hero against Green Bay, was traded to Buffalo. Productive linebacker Tremaine Edmunds was released. They didn’t really find an impact player on the defensive line or secure the left tackle spot.

So why is Jon Gruden so confident?

It is likely he can see what general manager Ryan Poles and head coach Ben Johnson are doing with the overall roster makeup. First and foremost? They got faster. If you look at every position group comparing 2025 to 2026, there is more explosiveness across the board.

Speed kills in the NFL. Then you have the developmental angle. Remember, the Bears accomplished their run last season thanks to major contributions from their 2025 draft class. If Colston Loveland, Luther Burden, and Kyle Monangai were that good as rookies, imagine what they would become with more experience and knowledge of the offense.

Finally, there is the health issue.

It is easy to forget that Chicago was one of the most banged-up teams for much of the season last year. Several of their most prominent players missed several games during the season.

• Austin Booker – 7 games
• Tremaine Edmunds – 4 games
• Kyler Gordon – 12 games
• Grady Jarrett – 3 games
• Jaylon Johnson – 10 games
• Rome Odunze – 5 games
• Noah Sewell – 6 games
• Tyrique Stevenson – 3 games
• Dayo Odeyingbo – 11 games

The truth is, we never saw this team at anywhere close to full strength. That they made the playoffs anyway should be taken as an encouraging sign of what they can accomplish in 2026. Odunze was on pace for a huge year before his foot problem. Johnson is a Pro Bowler when healthy. Booker finished the season strong once he regained his legs. Gordon is one of the best nickel corners in the league when he’s on the field. If the health issues subside even by 50%, the Bears will be a much stronger team.

Are they a favorite to win the title? No. There are more established contenders like Seattle, Los Angeles, and Philadelphia. However, Gruden’s choice to pick them as sleepers was not crazy. The reasoning was sound.

The Chicago Bears didn’t make any significant moves on the defensive line this spring, much to the consternation of fans and media. This unit ranked near the bottom of the league in both pressure rate and run defense. Yet they added no new starters. Their only additions were all depth pieces like Neville Gallimore, James Lynch, Kentavius Street, and 6th round pick Jordan Van Den Berg. It is plainly clear general manager Ryan Poles and head coach Ben Johnson are banking on Austin Booker taking a step forward while Dayo Odeyingbo and Shemar Turner return healthy. That seems a little too optimistic and unlikely to pan out.

So is there even a plan here?

Most likely. However, it involves something that fans don’t tend to have these days: patience. There isn’t much the Bears can do about it right now. They didn’t have much cap space to spend in free agency and picking late in every round made it difficult to land any quality defensive linemen in the draft. The unfortunate truth is that the team was pretty much stuck with their current setup even before the offseason began. However, things will take a considerable turn next year.

Ryan Poles will be freed to make moves in 2027.

Contract structures this year made freeing up money almost impossible without restructuring deals. That would’ve created a massive cap issue down the road. Poles has made it clear he doesn’t want to do this. However, things change drastically next year. Five prominent players on defense will have zero guaranteed money left on their contracts, meaning they can all be released for significant cap savings.

If the Bears were to release all five of those players, they would have just over $105 million in cap space. That would give Ryan Poles tons of wiggle room to go hunting for potential upgrades on both the free agent and trade markets. Some will argue it’s almost impossible to rebuild a unit in one offseason. Except we just saw Poles literally do that a year ago in 2025. In the span of two months, he overhauled the entire offensive line.

• Traded for Joe Thuney
• Traded Jonah Jackson
• Signed Drew Dalman
• Drafted Ozzy Trapilo

Before Trapilo got injured, that front was playing some really good football. One would think Poles is confident he can do it again, this time on defense.

The Bears could have some big opportunities.

Next year has a chance to be a really good one for defensive line options. We have edge rushers like Byron Young, Yaya Diaby, and Tuli Tuipulotu. Then you have interior pass rushers like DeVonta Wyatt, Kobie Turner, and Moro Ojomo. Obviously, not all of them will reach the open market. Yet if some of them do, the Bears will have more than enough cap space to take a couple of swings at some upgrades. This is before you consider the possibility of finding some bargains on the trade market.

Then they go into the 2027 NFL draft, where they will have almost their full complement of picks, including their top four selections. While early, many experts believe as many as ten defensive linemen could go in the 1st round alone, meaning it could be a really strong class. That would fall in line with one of Poles’ strengths as a general manager: being able to anticipate the future. We saw that when he bypassed Bryce Young and landed Caleb Williams a year later. If this plan is executed with the same urgency as last year with the offensive line, the Bears’ defensive front will look considerably better.

For most Chicago Bears draft classes, the players who tend to create the most excitement are the high picks. Last year, it was Colston Loveland and Luther Burden. However, every once in a while, a group comes along that delivers an unexpected surprise from the later rounds. Darnell Mooney immediately turned heads despite being a 5th round pick in 2020. The same was true of Jordan Howard in 2016, Adrian Amos in 2015, Johnny Knox in 2009, and Mark Anderson in 2006. It appears the same might be coming true with Jordan Van Den Berg.

It sounds odd. We’re talking about a 6th round pick. The hit rate in that draft range hovers between 3% and 9%. Not exactly encouraging odds. Yet that is what Jeremy Fowler of ESPN is reporting. Excitement for him inside Halas Hall is much higher than they’re letting on.

“The Bears believe they’re getting a steal with sixth-round defensive tackle Jordan van den Berg out of Georgia Tech. Several of his testing numbers hit the highest mark on the Bears’ internal scouting scale. My sense is the Bears have plans for him beyond that of a typical sixth-round flier and believe he was one of more gifted defensive tackles in the draft.”

It is easy to understand the testing part. Van Den Berg is 6’3″ and 310 lbs. He a 4.94 in the 40-yard dash, a 10-yard split of 1.61 seconds, and a 36-inch vertical jump. Oh, and he also put up 35 reps of 225 lbs on the bench press. The guy is a physical freak of nature.

So why did Jordan Van Den Berg fall?

That is the question many are asking. If he is such a good prospect, one would think he’d have gone far earlier in the draft. There are two factors involved. The most obvious is that he’s 24 years old. Teams generally don’t like drafting older prospects early. Then there is his college career. Van Den Berg spent his first three years with Penn State, during which he was strictly a backup. He finally transferred to Georgia Tech in 2024, where he started, but his season wasn’t anything special. Not until last year did things finally click for Van Den Berg, who finished with three sacks, 11 tackles for a loss, and 28 pressures.

This puts evaluators in a tricky spot. Did the light finally go on for Van Den Berg after getting his chance to play? Or was he an older prospect who took advantage of mostly younger guys to boost his stats? Everybody remembers Velus Jones. He did nothing for most of his career at Tennessee, but finally had a breakout season in his final year. By the time the Bears drafted him, he was turning 25 years old. As everybody saw, the last college season was nothing but a flash in the pan.

There are some things going in his favor.

For one, he’ll have Grady Jarrett as a mentor. The former Pro Bowler knows exactly what Jordan Van Den Berg is experiencing. Jarrett himself was a lowly 5th round pick once upon a time. He still managed to carve out an excellent career. There is no reason this kid can’t if he applies himself the right way. That means staying in shape and obsessively working on his craft. It is one thing to have elite athletic ability. None of that matters if you don’t know how to hand-fight, shed blockers, read play fakes, and collapse the pocket without being stalled out.

These are things that far too many young players never fully grasp when they get to the league. They grew so used to winning with pure talent in college. They don’t realize that everybody in the NFL is gifted. It is those who embrace the mental side of the game who become the best. The Bears seem to think he has the necessary qualities. This is somebody who chased this dream all the way from South Africa. He owns his own business. Dedication is nothing new to Van Den Berg, which means he’s already won half the battle.

Unless you’re just being stubborn, it has become apparent over the past two offseasons that there is a new sheriff in town. Ryan Poles is still the general manager of the Chicago Bears, but his roster power has shifted. Head coach Ben Johnson is the man with the final say on personnel matters. Multiple team insiders have confirmed it. If that weren’t enough, it isn’t hard to see the shift in the Bears’ priorities since he came on board. A lot of it is great. Johnson is putting more focus on high-level competitors, seeking players who really love the game. Violence and intelligence are two keys. None of this is bad.

However, there is one growing concern arising from the 2026 draft. Is Johnson favoring the offense too much?

The Bears have made eight picks in the first three rounds over the past two drafts. Six of them came on the offensive side of the ball. On the surface, it shouldn’t be a surprise. Johnson is an offensive-minded coach. It would make sense he’d want to stack that side of the ball with talent. Some just feel this favoritism is coming at the cost of the defense, which ranked 29th last season. The fear is that this approach may ultimately hurt the team in the long term. It is hard to win championships when you’re constantly trying to outscore opponents.

Ben Johnson isn’t in uncharted territory.

There have been several NFL head coaches who wielded personnel authority on their teams. The interesting part is that many of them tended to go in the opposite direction. Offensive experts drafted defense high and defensive experts drafted offense high. Others tried to keep a relative balance. A good example is Dave Wannstedt. During his first two years in Chicago, where he had final say, he drafted three offensive players and three defensive players in the first three rounds. Is Johnson an outlier in this way?

Not exactly. One prominent coach who had no qualms about showing favoritism to his side of the ball was Hall of Famer Bill Parcells. When he gained that authority with the New York Jets in 1997, five of the six picks made in the first three rounds were defense.

He wasn’t alone. Mike Holmgren, fresh off winning a Super Bowl with the Green Bay Packers, took over the Seattle Seahawks in 1999 and was given full personnel authority. He proceeded to do the same thing, grabbing offensive players with five of the seven picks he had in the first three rounds.

So is this style of drafting doomed to fail?

Well, no. Not entirely. Parcells’ two drafts didn’t amount to much aside from James Farrior, who would become a two-time Pro Bowler, but that was with the Pittsburgh Steelers because the head coach abruptly resigned in 1999. Holmgren had more success. Alexander became a league MVP and a central part of Seattle’s Super Bowl run in 2005. Jackson was a three-time 1,000-yard receiver. Steve Hutchinson, whom the coach drafted in 1st round in 2001, is in the Hall of Fame. Much of this comes down to a coach’s eye for talent.

We already saw last year that Ben Johnson is pretty sharp. Colston Loveland, Luther Burden, and Kyle Monangai all had excellent rookie seasons. So it might be okay to trust him when he went on that offensive spree on day two of the draft last week. Still, if his goal is to win a championship as he claims, he can’t keep neglecting the defense every year. Champions aren’t built through hope and luck. He isn’t an offensive coordinator anymore. His job is to build a team, not just an offense.