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.
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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.
| Position Group | 2025 Avg 40 Times | 2026 Avg 40 Times |
|---|---|---|
| Wide Receivers | 4.46s | 4.39s |
| Running Backs | 4.51s | 4.48s |
| Tight Ends | 4.74s | 4.70s |
| Quarterbacks | 4.59s | 4.59s |
| Offensive Line | 5.18s | 5.10s |
| Interior D-Line | 5.03s | 4.92s |
| Edge Rushers | 4.78s | 4.72s |
| Linebackers | 4.68s | 4.54s |
| Safeties | 4.57s | 4.44s |
| Cornerbacks | 4.50s | 4.46s |
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.
