A Love Letter to Karoline Leavitt, the GOAT of White House Press Secretaries

AP Photo/Mark Schiefelbein

From predicting Donald Trump’s victory in 2024 to nailing the Democrats' Graham Platner bait-and-switch a month before everyone else, my predictive hit rate is among the best in the punditry biz. (And just this week, 48 hours after I hailed AOC’s “woke” pivot as a PR masterstroke, she shot to the top of the prediction markets. Booyah!) No, I haven’t gotten everything right, but to be fair, I’ve taken some very yuuuge swings. (Go big or go home, amiright?)

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I’d guesstimate my accuracy is about 75%.

But one of my proudest prognostications was less a prediction than an observation: Almost immediately, I hailed Karoline Leavitt — the youngest White House press secretary in history — as a frickin’ rockstar, and the greatest to ever serve President Trump.

From March 18, 2025:

We’re now eight weeks into Donald Trump’s second term, and two things are perfectly clear: 

  1. His press secretary, Karoline Leavitt, is an absolute rockstar.
  2. The mainstream media hates her.

The difference between Karoline and, say, Sean Spicer — Trump’s original press secretary — is night and day. Look, I don’t want to be unkind to Spicer, but her charisma, charm, and intellectual dexterity leave him in the dust. It’s the difference between chicken salad and chicken [EXPLETIVE].

Personally, I think she’s the best press secretary President Trump’s ever had…

It took the rest of the media a little bit longer to catch up. People forget, but Leavitt was initially dismissed as a dumb blonde bimbo who only got the job ‘cause she’s young and hot.

Fast forward to the summer of 2026, and check out what the same mainstream media is saying about her resignation from the White House:

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CNN: Why Karoline Leavitt Might Be Impossible for Trump to Replace

The Hill: Trump Faces Tough Task in Replacing Karoline Leavitt

Wall Street Journal: Karoline Leavitt, the Press Secretary Who Perfected the Art of Defending Trump

Financial Times: Donald Trump Loses His Favourite Press Secretary as Karoline Leavitt Exits

Monocle: How Karoline Leavitt Became the World’s Most Famous White House Press Secretary

LA Times: White House Press Secretary Karoline Leavitt, One of Trump’s Top Advocates, to Step Down

Fox News: White House Correspondents Widely Praise Karoline Leavitt as She Announces Exit From Trump Administration

Reason Magazine: How Karoline Leavitt Changed the White House Press Room

USA Today: Karoline Leavitt Exposed the Democrats’ Double Standard on Women

And we KNOW she wowed ‘em, because the mainstream media is actually blaming President Trump for her exit! (See, according to the ol’ rumor mill, Trump called her too many times when she was on maternity leave. And clearly, a pregnant woman would have ZERO interest in talking to the president.):

New York Magazine: Trump’s Constant Calls to Karoline Leavitt Really Backfired

Fast Company: Karoline Leavitt Resigns After Trump Kept Calling Her on Maternity Leave, Sources Say

New Republic: Karoline Leavitt Quit Because Trump Was Driving Her Crazy

The Daily Beast: Trump’s Incessant Calls to Karoline Leavitt, 28, Exposed

Times of India: Trump’s Calls to Karoline Leavitt During Maternity Leave Come Under Fresh Scrutiny

OK Magazine: Donald Trump Repeatedly Called Karoline Leavitt Asking When She Would Be Back From Brief Maternity Leave Before Her Resignation, Insiders Claim

Irish Star: Trump Hounded Karoline Leavitt for Maternity Return Date as White House Had No Replacement

The Mirror: Trump Pressured Leavitt on Maternity Leave Return in Relentless Calls as Replacement Remains Mystery

Radar Online: Trump ‘Repeatedly’ Contacted Karoline Leavitt During Maternity Leave to Ask When She Was Returning — as Press Secretary Weighed Quitting Job

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Ain’t that a kick in the head: Within 20 months, Karoline Leavitt went from an “airhead” to irreplaceable!

Yet her biggest legacy will be how she transformed the position of White House press secretary. Pre-K.L. and post-K.L. are gonna be night and day. What once was an afterthought is now a PR priority.

She turned White House press secretary into a prestige position.

In the past, it was hit and miss. Sometimes, the White House press secretary was competent; sometimes, he/she wasn’t. Either way, nobody gave it much thought. (And at least one president clearly prioritized DEI box-checking over PR talent.)

But the era of appointing uncharismatic lumps such as Robert Gibbs, Jay Carney, Karine Jean-Pierre, and Dee Dee Myers to the position is over. It’ll NEVER happen again. 

That’s because Leavitt redefined the political — and personal — utility of being White House press secretary.

It’s a byproduct of our media age: Voters consume content in quick bites, conflict sells, and viral moments are manna from heaven. Some of the top conservative podcasters and media personalities (including Charlie Kirk) had to manufacture conflict by traveling to college campuses, debating left-wingers, and uploading the most viral encounters to YouTube. 

Kirk and others invested in this strategy because it moved the needle — repeatedly.

But the White House press secretary doesn’t have to travel anywhere. Whenever she wants, she can go to the podium, whack reporters around like a piñata, and become an instant social media sensation.

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It’s an ambitious politician’s passport to fame and stardom!

Pre-K.L., someone such as Scott Jennings would have had no interest in being the White House press secretary. Why would he? He’s already kicking [tush] on CNN as the network’s top conservative counterweight; why deal with the headache of pushy left-wing reporters? Why hitch your wagon to the lame-duck Trump administration when you’re doing just fine on your own? (CNN pays him with real money, y’know.)

Now, it’s a very real possibility — because Karoline Leavitt went from MEETING the press to BEATING the press.

With the D.C. press corps’ blistering hatred of Donald Trump and the MAGA movement, the purpose of the White House press secretary changed out of necessity. The goal, after all, of the mainstream media wasn’t to report “without fear or favor,” but to cheerlead for the Democrats and undermine the Republicans. In such a climate, a by-the-books, dispassionate PR presentation would be a disaster.

You can’t treat a bad-faith question like a good-faith question. It just doesn’t work.

Which is why Karoline Leavitt didn’t try:

The purpose of the position has changed. Instead of serving as the media’s punching bag, Leavitt reversed the equation, flipped the narrative, and leveraged the media’s idiocy to punctuate her own political points — manufacturing viral moments by the barrelful.
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Best of all, she instinctively mirrored her boss’s ethos: Trump is a fighter; so is Leavitt. If you come after Trump with a hammer, he’ll fire back with a torpedo. His tolerance for stupidity is famously thin.

Same goes for Leavitt.

Plus, she had fun with the gig. Her joy was genuine; it leaped through the screen. Whether the next press secretary is Scott Jennings, Kari Lake, Spencer Pratt, or someone else, Leavitt created the blueprint that her successor will surely follow.

Post-K.L., the primary job of a Republican White House press secretary is to produce viral moments by out-sparring D.C. reporters. Each day you’re behind the podium, your goal is the same: Defend the president by excoriating his detractors — and exposing their left-wing bull[feces].

It’s now a debating position, not an information desk.

Which, in all honesty, is way more fun: Not too many elite political talents would sign up to be the media’s punching bag ‘til the end of 2028… but getting two solid years of primo media facetime? Going one-on-one against America’s most famous journalists? Your top moments uploaded to X? Smashing reporters on a daily basis? 

Hooboy!

The media is our perfect foil. Just 28% of Americans trust it — and for Republicans, it’s just 8%. We couldn’t ask for a better enemy.

Post-K.L., the position of White House press secretary could elevate a current media star such as Scott Jennings to the next level for superstardom.

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After leaving D.C., Karoline Leavitt will have plenty of options. If Fox News is wise, it’d load a Brink’s truck and make her an offer — as should CNN, Newsmax, and the major networks. She’d also be a helluva pick-up for The Daily Wire (assuming they could afford her).

Or she could launch a digital network of her own, a la Tucker Carlson, Candace Owens, and Megyn Kelly. She has the name I.D. and political credibility to draw millions of eyeballs right out of the gate. Everyone knows her; everyone respects her.

She’s about to be the hottest free agent in all of political media!

Or maybe she’ll take some time off and be a full-time momma for the next few years. Lord knows she’s earned the right to rest — and focus on her babies. 

She’s still only 28.

Because, unlike most members of the media, she doesn’t have to strike when the metal is hottest. We won’t forget her — and her career won’t suffer. She can afford to take her time.

Because she’s simply too talented.

Congratulations, Karoline. You’re the GOAT of White House press secretaries. You were so damn good, you changed how the entire game is played. We salute you.

And it was the easiest prediction of my career.

One Last Thing: 2026 will reach a crescendo with the midterm elections. Nothing less than the future of our country teeters in the balance.

Never before have the political battle lines been so clearly defined. Blue wave or red wall, one way or another the 2026 midterms will transform our country.

We need your help to win the media war!

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