Honestly, if you look at the schedule and see the Chicago Bears and Raiders lining up against each other, you might not immediately think "blood feud." It’s not Bears-Packers. It’s not Raiders-Chiefs. But there is a weird, gritty undercurrent to this matchup that keeps it fascinating, especially after what we just witnessed in the 2025 season.
The history between these two goes back to 1972, but the modern era has turned it into a bizarre chess match of "what ifs." Most people think of these teams as being in totally different universes because of the conference divide. They aren't. They are mirror images of franchises trying to find a permanent identity while leaning on terrifying defensive ends and "hope" at quarterback.
The Blockbuster Drama Nobody Expected
Let’s talk about what actually happened recently because it changed the vibe of this entire series. On September 28, 2025, the Bears and Raiders played a game at Allegiant Stadium that was, quite frankly, a heart-attack inducer.
The Raiders were leaning on rookie sensation Ashton Jeanty, who was basically a human cheat code that day. He ripped off a 64-yard touchdown run and finished with 138 yards on the ground. For three quarters, it looked like the Raiders were going to bully the Bears right out of Vegas.
But then Caleb Williams did that thing he does.
With 1:34 left on the clock, Williams capped off a 69-yard drive by handing it to D'Andre Swift for a two-yard score. It put the Bears up 25-24. But the game wasn't even over then. The Raiders marched down, set up for a potential game-winning 54-yard field goal, and Josh Blackwell—a guy mostly known for special teams—came off the edge to block it.
Game over. Bears win.
That game was a microcosm of the Chicago Bears and Raiders dynamic: pure chaos, elite individual performances, and a finish that left Raiders fans wondering why they can't ever just have a "normal" Sunday.
The Maxx Crosby Factor and the Trade Rumors
You can't mention these two teams in 2026 without the elephant in the room. Maxx Crosby.
🔗 Read more: Are the Los Angeles Dodgers Playing Today? Everything About the 2026 Schedule
There is a segment of the internet—mostly Bears fans on Reddit and X—that is convinced Crosby is the "missing piece" for Chicago. It’s not just baseless speculation anymore. In late December 2025, reports surfaced that Crosby was visibly frustrated with the Raiders' direction, even allegedly leaving the facility in anger after being told he was being shut down for the season.
The connection is obvious. Chicago has Montez Sweat, but they need that secondary "monster" on the edge. The Raiders, meanwhile, are in a weird spot with a new coaching vacancy after Pete Carroll’s short-lived stint ended in January 2026.
- The Price Tag: Experts like Bill Barnwell have floated trade pitches involving multiple first-round picks.
- The Fit: Crosby’s "motor" is legendary. Putting him in a defense with Tremaine Edmunds and a secondary led by Jaylon Johnson and Kevin Byard? That’s a nightmare for the NFC North.
- The Reality: The Raiders don't trade "The Condor" unless the building is literally on fire. But the fact that Chicago is even in the conversation shows how much respect the league has for the roster Ryan Poles has built.
Caleb Williams vs. The Silver and Black
What most people get wrong about Caleb Williams' performance against the Raiders is the stat line. If you just look at the box score—22 for 37, 212 yards, 1 TD, 1 INT—it looks mediocre.
It wasn't.
The Raiders didn't blitz much (only about 24% of the time), but when they did, Williams was surgical. He completed 5-of-8 passes against the blitz for 63 yards and a touchdown. He was playing chess against a Raiders defense that featured a relentless Maxx Crosby, who, despite not getting a sack, had an interception and a forced fumble in that game.
It was a battle of "New Era" vs. "Old School Grit." Williams proved he could handle the pressure of a hostile road environment, which is something Bears QBs of the past usually failed at.
A History of Swapped Stars
The connection between the Chicago Bears and Raiders isn't just about the games. It’s the DNA.
Remember the Khalil Mack trade? That move defined both franchises for half a decade. The Bears gave up a king's ransom to get a Hall of Fame talent in his prime. The Raiders got the picks that eventually became... well, a mixed bag.
These teams trade identities. They trade players. They even trade philosophies. The Raiders' "Commitment to Excellence" often looks a lot like the Bears' "Monsters of the Midway" when things are going well. When things are going poorly, both fanbases suffer in the exact same way—with loud, passionate, and often hilarious frustration.
Key Takeaways for the Next Matchup
If you're betting on or just watching the next time these two meet, keep these specific factors in mind:
- The Ashton Jeanty Problem: If the Raiders keep feeding Jeanty, the Bears' front seven has to be more disciplined. Giving up 240 rushing yards like they did in 2025 is a recipe for a loss, regardless of Caleb Williams' heroics.
- Special Teams Matter: In a series decided by one point (25-24), the difference was a blocked field goal and Cairo Santos going 4-for-4. Don't ignore the kickers.
- The Secondary Battle: Kevin Byard III and Tyrique Stevenson have become a "no-fly zone" for Chicago. The Raiders' QB situation (which has been a revolving door lately) will struggle if they can't find a way to manipulate those safeties.
The rivalry might not have a trophy or a cool name, but the Chicago Bears and Raiders games are increasingly becoming the "Proving Ground" games for both teams.
If you're looking to track the next step for either of these teams, keep a very close eye on the Raiders' head coaching search this month. Whoever they hire will determine if Maxx Crosby stays in the Silver and Black or if the rumors of him moving to the shores of Lake Michigan actually have legs. Following the draft pick value charts for 2026 will tell you exactly what the Bears might have to give up if they want to make that blockbuster happen.