Karoline Leavitt Sends The Ugly Libs A Selfie, Katherine Webb Stuffed Into A Holiday Dress & Trump's Coin Toss

Two Mondays in December down. Two to go after today. We're at the halfway point of the month, boys and girls. It's halftime. Take a breath. Head to the locker room. Get you some orange slices and a Gatorade, watch some film, and gear up for what I suspect will be a WILD second half. 

This is the final full week before Christmas. We're at the 10-day mark. Ten days. 

We've got college football playoffs starting THIS WEEK. We've got bowl games – what's left of ‘em, anyway. We’ve got the final quarter of the NFL season. We've got basically four holidays crammed into a week (Christmas Eve, Christmas, New Year's Eve and New Year's Day). 

It's a loaded potato of a month coming our way. Let's ATTACK it. 

Welcome to a Monday Nightcaps – the one where Karoline Leavitt and Margo Martin send the LIBS a selfie from Air Force One. 

What else? I've got the best of the rest from a loaded weekend of #content, my high school football team suffered unfathomable heartbreak Saturday night, Crimson Tide First Lady Katherine Webb checks back in, and Trump's coin toss at Saturday's Army-Navy game has my brain in a pretzel today. 

Insane behavior. 

OK, grab you a stiff drink and make it a DOUBLE, because we all have to watch the Dolphins in primetime in a few hours, and THEN settle in for a Monday 'Cap!

Is this the worst clock management of all time?

Before we get into it … please don't bet my Dolphins tonight. I'm just telling you, don't do it. A primetime game, on the road, in the cold? Aaron Rodgers could be 150, and I still wouldn't take the Dolphins. 

Geoff Clark made the Fins at +3 his Newsletter bet of the day this morning, and I couldn't believe it. They never learn. Hope Geoff's right, but I ain't holding my breath. 

OK, now to a real football team … 

My Vero Beach Fighting INDIANS lost an absolute heartbreaker Saturday night in the 7A state championship. We were going for our first title since 1981. We led 27-11 with 12 minutes to play, and 27-19 with 1:30 left, and the BALL. 

We needed a first down to ice the game. You will NEVER, in a million years, guess what happened next:

That play went internet-viral Saturday night to Sunday morning. Clay retweeted it. My great governor retweeted it. 

But folks down here in Vero don't care about the final play. How could you, when the previous Vero possession was the most pathetic thing I have ever witnessed in my entire life. 

Vero had the ball, needing a first down to ice the game. One minute left. The other team had two timeouts. 

Instead of running a play on any of the next three snaps … head coach Lenny Jankowski chose to kneel all three times. 

What a weekend of #content!

First down: knee (timeout)

Second down: knee (timeout)

Third down: knee (clock runs)

Fourth down: Take an intentional safety (!!!) in order to run more time off the clock!

That made it a 27-21 game. We took an eight-point game, and made it a six-point game. Amazing. 

I was listening to the game on my couch with a tumbler of whiskey like a real man, and fell asleep with Vero up 21-11. I woke up as the safety was happening, and I had never, in my life, been more confused. 

Can anyone in class today top this as far as heartbreak goes? It's been nearly 48 hours, and I still can't fathom what he was thinking on the final drive. There's just no explanation. None. 

This is high school football in 2025. Vero is a powerhouse. Every single big time D1 recruit in the state is on this team. The offense scores a billion points a game. 

And you … take THREE knees when you only need 10 yards to win your first state title in 40+ years? What world am I living in? 

Unreal. 

OK, enough bitching from me. Let's get to the best #content from a huge weekend:

Phil, Karoline, Margo & Katherine, oh my!

What a weekend. What a day of football we got yesterday. I was locked in on Philip Rivers at 4:25. I hadn't felt a rush like that in ages. 

Couple thoughts …

1. What a coin toss. Have we been doing it all wrong?

2. My fantasy team that got ousted in the final week of the season last week scored 200+ points yesterday and it didn't matter. Every. Single. Year. 

3. Sleepy Joe!

4. Love Gia Duddy, but … that's just a shirt. It's a giant dress shirt. That's it. Not complaining, just correcting. 

5. The Cowboys loss last night was the most predictable thing of the day. 

6. As was Philip DAMN Rivers slinging the rock like a Hall of Famer. Speaking of …

Let's rapid-fire this Monday class into a painful night of Monday Night Football. I could watch these two clips over and over again. And, frankly, I have:

Goodness gracious. How great is Phil? I was such a Philip Rivers fan back in college, mainly because he was playing at the same time as Brady, Manning, Big Ben and Brees, and I felt like he always got overshadowed. 

So, whenever he lit someone up, I couldn't get enough of it. There are so many insufferable players in the NFL nowadays. Hell, football in general (looking at you, Diego). 

Phil is one of the good ones. What a damn ballgame. 

Next? Look who is BACK, just in time for the holiday season!

Been a MINUTE since Katherine Webb made any noise, but buddy, the fastball clearly still plays. Welcome back to the show, Katherine! And just in time for the playoffs. 

Feel like ‘Bama’s gonna need her this weekend. 

OK, that's it for today. Good start to the week. Here's Karoline Leavitt and Margo Martin sending the Libs into a free-fall to start the week. 

See you Wednesday. 

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

Thoughts on the Vero ending? Email me at Zach.Dean@OutKick.com.