Tony Romo Is Back To Being Insufferable, Riley Gaines Humiliates Crazy Keith Olbermann & Maggie Sajak In Italy

Yes sir! We've reached the middle of September, and fall is in the AIR here in Florida. True story. 

I was on a walk yesterday evening during the 4 p.m. window of NFL games with my kid, and I felt it in my plumbs. Was it cold out? Hell no. Wasn't even cool. But I didn't sweat at all during the walk. I could actually breathe, which meant the humidity wasn't 1,000%. 

There was a breeze. Someone had a tiny scarecrow by their door. 

I knew, right then, that it was almost here. Whenever I can come back home after a 30-minute walk and not look like I just ran the Boston Marathon, it's a win. And it means we're close. So close. Let's keep up the momentum this week. 

On that note, welcome to a Monday Nightcaps – the one where we check in with Tony Romo after an insufferable day calling the Chiefs game, and then do the same with Cris Collinsworth and Caleb Williams. 

My God, Cris. We get it. You love Caleb Williams. Every time the kid dropped back and threw it straight, Cris stitched up another thread on his gold jacket. It was insane. 

What else? I've got Maggie Sajak dominating a French Riviera, Riley Gaines stuffing Keith Olbermann in a locker over the weekend, and I've got to give the Libs credit today. Seriously. 

You heard of a Friday news dump? In this business, that's what we call something big and newsworthy that happens on a Friday afternoon when nobody cares. It's a tactic, and a smart one. 

Well, buddy, we got a Sunday afternoon news dump yesterday when someone tried to murder Donald Trump for the second time in as many months. It happened during a loaded, 10-game slate of 1 p.m. NFL games, and I'll be honest with you … I had NO idea it happened until late last night. None. 

Unless Scott Hanson put Trump's golf course in one of his octo-boxes, I missed it. Again, brilliant move by the left. Kudos. 

OK, grab you something tall & strong, slug it down like the true Patriot you are, and settle in for a Monday 'Cap!

Let's check in with Tony Romo for the first time this year

It took a whole … one week … but we're OFF TO THE RACES with the Tony Romo SUCKS takes this 2024 NFL season. 

For those who missed it – you didn't, because it was the only watchable 4 p.m. game – the Chiefs hosted the Bengals yesterday. Naturally, Jimmy Nantz and Tony Romo were on the call, because they have to call at least eight Chiefs games a season, per their contracts (allegedly). 

Tony, notoriously, is OBSESSED with Patrick Mahomes. He loves him. Pat Mahomes and Josh Allen. Those two QBs just get the job done for Tony Romo. 

Anyway, pretty much all of the country turned on Tony last season because he went from fun broadcaster to this guy won't shut the hell up in three seasons, and he was back in his bag yesterday. 

Nice toss, Pat! 

Best of the rest from a big weekend of content 

I mean, I could go on and on. The comments were a wasteland. I'm telling you, Patrick Mahomes could commit murder on live TV with Tony in the booth and Tony would shout at Jim for 30 seconds about how intricate it was. 

We excited about four more months of Tony Romo? Lord knows I am, mainly for content like this. We're just getting started, baby. Buckle the hell up!

PS: Brady was noticeably better yesterday, as I told you he would be. Night and day from Week 1. 

PPS: Collinsworth was Tony Romo Lite when it came to Caleb Williams last night. Seriously, you would've thought Caleb was the second coming of Jesus Christ. Guy could do no wrong. 

In fact, let's have here's a guy Cris lead us off in today's Best of the Rest From A Big Weekend of Content portion of class. 

Riley torches crazy Keith, Sean Payton's decision & Maggie in Italy

No. 1: How great is Kevin Harlan? The guy is by far the best in CBS' NFL stable and it's not particularly close. Oh yeah! He also went on DAN's OutKick show today. 

CBS let one of their own cross party-lines? To OUTKICK, no less? I knew Kevin was a Republican. Love that dude. 

No. 2.: Insane stat on the UNLV kid. Here's his mom, for those who are obviously wondering. She's a real estate broker now!

Hilarious. What a world. 

OK, rapid-fire time on this third-Monday-of-September! First up? Riley murdered poor Keith Olbermann over the weekend. 

What a tweet:

Keith vs. Riley is such a mismatch, it's insane. It's basically anyone who plays Bryce Young and the Panthers right now. Mismatch of the century. You know it's going to be a bloodbath every single time. 

PS: is Bryce Young the worst NFL QB of all time? I'm not even joking, he's THAT bad. Wild. He was just benched for Andy Dalton. 

Next? Let's check in on Broncos fans this morning after Sean Payton decided to play defense yesterday, down 7, with two minutes left:

WHAT?? In what world is kicking off and getting the ball back with maybe 26 seconds left, needing a touchdown, a better option than trying an onside kick? This is the guy who literally opened the second half of a Super Bowl with an onside kick! He knows they can work. 

Granted, that was the element of surprise, but still … I don't think there was a dumber decision in the NFL yesterday than that one. Nuts. 

Also … remember all the Bo Nix preseason hype? Whoooooooooooooooof:

Yep. Broncos are in trouble, buddy. Maybe it wasn't Russell Wilson? 

Just kidding! It's ALWAYS Russell Wilson's fault around here. Always. 

OK, that's it for today. I know – short class – but I've got a sister-in-law to pick up from the airport and I-4 traffic to navigate. 

Wish me luck. 

Take us into the week, Maggie!

OutKick Nightcaps is a daily column set to run Monday through Friday at 4 p.m. (roughly, we’re not robots).

You as annoyed with Romo as I am? Email me at Zach.Dean@OutKick.com.

Written by
Zach grew up in Florida, lives in Florida, and will never leave Florida ... for obvious reasons. He's a reigning fantasy football league champion, knows everything there is to know about NASCAR, and once passed out (briefly!) during a lap around Daytona. He swears they were going 200 mph even though they clearly were not.