Jenny Dell Ditches Her CBS Outfit For Something More Revealing, Maggie Sajak In Overalls & SNF Jockey Intro!

First Monday of May? Cinco-de-Mayo? The influencers updating their Instagrams with the weekend's Kentucky Derby #content? Game 1 of Panthers-Maple Leafs tonight? 

Not bad, boys and girls. Not bad at all. Summer is so close I can taste it. I can feel it in my plumbs. We're creeping up toward the 90s this week in Florida. The sun is sunning until nearly 8. Yesterday, I believe, was the four-month countdown to the return of football season. 

It's 119 days from now, we're all going to be off on a Labor Day Monday getting ready for a slate of college football games. We're in good shape right now. Let's keep Lady 'Mo on our side as we barrel into a new month. 

Welcome to a Monday Nightcaps – the one where we enjoy the Kentucky Derby with CBS's Jenny Dell, and go from there. 

What else? I've got plenty more from Churchill Downs from Saturday, a loaded weekend of #content, Food Network's Giada covers herself in some tomato sauce, and Maggie Sajak stuffs herself into a pair of overalls. 

Oh yeah! I've also got an absolutely ELITE ‘fore’ call yesterday from Jordan Spieth. He's a #content machine, and this one may be my favorite moment yet. Incredible. 

Grab you something culturally relevant on this day – perhaps from Trump Tower, if you're close by – and settle in for a Monday 'Cap!

Amen to this

Still my favorite tweet of all time, and it's not even close. Trump pumps out a lot of insane crap, but that little gem from 2016 was really the beginning of it all. Little did we know back then what that would turn into. 

Now, I don't feel like getting overly political today. Some days I do. Today, I do not. I'm tired. I've spent the last three weekends traveling back and forth for weddings or art markets. My 8-month-old hasn't slept since Christmas. We start sleep training on Wednesday (true story). I don't feel like talking politics today. 

That being said, this little Trump nugget from over the weekend hit me straight in the gonads. I felt it, and I'll tell you why – because I literally live it every single day. 

Every. Single. Day. 

What a weekend of #content!

It's just so true. My house is just filled with useless toys that our kids never, ever touch. My toddler has 60 stuffed animals between her room and the living room. That's not hyperbole. I counted this morning. Sixty. 

Trump is a billion percent right on this one. Sorry, Libs, but even you have to agree with him here. 

The clutter is out of control. Last night on my way to my kid's room after he woke up promptly at 11 p.m., I stepped on four legos, kicked an Elmo, stubbed my toe on some stupid computer game, and nearly face-planted on a life-size stuffed animal dog. Who needs a life-size stuffed animal dog? Besides Herbstreit, of course. 

Anyway, if tariffs get rid of that, I'm all in. I don't care if we have to eat ramen for the next four months. I'll take it. If I can walk 30 feet from my bedroom to the other side of the house without risking an orbital fracture, I'll nominate Trump for the Nobel Peace Prize myself. 

Make America Less Cluttered Again!

OK, let's get to the #content from one of the more loaded weekends in a while. Yes, it will be Derby-centric … starting with Livvy!

NHL playoffs win again, Jordan's warning & Saucy Giada!

What a way to kick-start the month of May! Good work from everyone involved! Couple thoughts …

1. Tan line Livvy at the Derby? That'll play. Lord knows it ended better than it started. You'll see. 

2. Jenny Dell and Kay Adams back-to-back? Most formidable sportscaster lineup in the league right now. Rivals the '27 Yankees. 

3. Zuck and Theo? My God. What's going on there? I can't think of two dudes who are more polar opposites. Maybe the interview got better after that. No shot I'll ever make it that far, though. 

4. Back to Livvy … she starts our rapid-fire portion of today's class, and it ain't for anything good:

Yeah, I mean, that was brutal. Not Livvy's best. Not saying it's her fault, but that was a tough watch. 

Nobody in the history of time has ever said, ‘Thank God that only lasted 12 seconds,’ when talking about Olivia Dunne, so this was certainly a first for society. 

I believe she has since said it was so awkward because there was an echo in her ear, which – God, I hope that's true. Certainly plausible. 

Still, it wasn't the greatest start to Derby weekend. Good rebound with the tan lines, though. Vet move. She reeled us right back in!

Next? We don't talk a ton of NHL here, but last night's game deserves some love. There is no better playoff atmosphere in the world than an NHL arena. None. Zero. It's not even close. 

I mean, just listen:

Two great calls. You're just not going to find a better crowd reaction. It was awesome. I think my Mount Rushmore of playoff atmospheres, purely based on the crowds and the pressure, would look something like this:

1. NHL Game 7 

2. MLB Game 7

3. Any back nine of a major with Tiger on the hunt

4. SEC championship game

That's probably not a definitive list because I'd need some more time to workshop it, but it's pretty close. No, the Super Bowl doesn't even sniff it. Real fans don't go to the Super Bowl. It's all corporate big-wigs. 

I could probably be convinced to slide in a Final Four game at No. 4. First three are pretty locked in. 

OK, a couple of real quickies on the way out. Scottie won yesterday by a billion because he's an alien, but the real story of the day was this move by Jordan Spieth:

Amazing. Nothing fires me up more than a clearly annoyed/checked out Jordan Spieth. He's the best thing going on tour right now as far as the #content goes. 

Sort of like Giada when it comes to the food industry:

Take us home, Farmer Maggie!

Goodness gracious … welcome back to class, Giada! Been a while, but you're back with a BANG. Nobody in the food industry does it better than Giada, and she'll be 55 this summer!

Forget Cinco-de-Mayo – let's all whip up some pasta tonight in honor of Giada and have ourselves a big start to the week. 

Take us home, Maggie Sajak! 

See you Wednesday. 

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

Your house sound as challenging as mine? 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.