Cowherd & Middlekauff: Split on Cowboys vs Raiders on Monday Night

We were finally able to pick a winner on a Monday night with Eagles over Packers last week. This time around? Not so easy. Dallas heads into Vegas laying three points against the Raiders, and we’re split. One of us is leaning into the star on the helmet, the other’s hunting for an upset on prime time.

Cowherd: Dallas is Built for This Spot

When I watch the Cowboys, I see structure. I see a team that’s gotten past its early-season wobble and settled into what they are – fast, organized, physical, and decisive. Dak Prescott has quietly strung together one of the cleanest stretches of football in the league, and the offensive line is finally healthy enough to let him breathe.

It’s not always flashy, but Dallas has become the rare team that wins the way veteran teams do: controlling tempo, dominating field position, and forcing turnovers instead of praying for them.

And let’s be honest: the Raiders don’t have an identity right now. The Pete Carroll experiment – and yes, it’s still weird to say “Pete Carroll, Raiders coach” – feels like it’s missing a gear. They’ve got young talent, sure, but it’s all over the map. Jeanty’s shown flashes, Geno’s been up and down, and the defense looks like it’s still stuck in preseason mode.

This is one of those classic spots where good coaching, a top-five quarterback, and a pass rush that gets home make all the difference. Dallas doesn’t need style points here. They just need to be themselves – efficient, aggressive, and mistake-free.

Give me the Cowboys to win and cover. Vegas can hang for a half, but over four quarters, the better roster pulls away.

Middlekauff: The Case for the Raiders – Barely

I get why Colin likes Dallas. Everyone does. Which is exactly why I don’t.

We’ve seen this movie before: a primetime Cowboys game, big buildup, everyone leans in on the favorite, and then suddenly it’s the middle of the third quarter and the underdog is hanging around. I’m not saying the Raiders are better – they’re not – but these Monday night games have a funny way of turning messy.

Maybe it’s the short week for Dallas, maybe it’s the travel, maybe it’s just the league’s parody finally catching up – but I’ll take the points and hope Pete Carroll’s got one trick left. This feels like a “backs-against-the-wall” week for him. They’ve been embarrassed twice in a row, the home crowd will be loud, and if Jeanty can get going, they can make this ugly.

And if there’s one thing Dallas doesn’t love, it’s ugly. They want rhythm. They want structure. Break that up, and suddenly Dak starts forcing throws, Schotty gets conservative, and the Cowboys start settling for field goals instead of touchdowns.

So yeah. I’ll take the Raiders. Not because I love them, but because Monday nights can be wild, and wild is usually good for the dog.

Cowboys at Raiders MNF Picks

Cowherd: Cowboys -3
Middlekauff: Raiders +3

Whichever way you lean, buckle up for this one.