Tag: Prep

Sometime after running for Congress in New Hampshire and before being named President-elect Trump’s White House press secretary, Karoline Leavitt was nice enough to fill in for me on The Grace Curley Show during my maternity leave.

I wouldn’t claim that those three months led Karoline — whose résumé includes work for Kayleigh McEnany, Elise Stefanik and Trump — to the White House. But I would argue that hosting a talk show is great preparation for the James S. Brady Press Briefing Room.

First off: she knows that if you lose your temper, you lose. Throughout summer 2023, Karoline heard from listeners about a host of issues, including the Republican primary candidates. A lot of listeners were thrilled at the prospect of former President Trump’s vying for a second term. Then again, plenty (myself included) were not fully convinced he had the kind of broad GOP support he would need to pull off a decisive victory. Karoline, while always respectful to Trump’s detractors, was unmovable. She calmly made the case for Trump at every opportunity — and when she wasn’t promoting his first-term accomplishments, she was listing Biden’s failures in regard to the open southern border or sky-high inflation. If a caller ever got under her skin, you would never have known it.

That kind of steely resolve was on full display a little less than a year later when Karoline, as Trump’s campaign press secretary, faced off with CNN’s Kasie Hunt in a fiery exchange just days before the first presidential debate. Karoline pointed out that CNN’s debate moderator Jake Tapper had compared Donald Trump to Adolf Hitler, causing Hunt to melt down before warning, “We’re going to stop this interview if you are going to keep attacking my colleagues.”

Ignoring Hunt’s increasingly high-pitched tone and patronizing warnings, Karoline continued to call out Tapper’s comments about the former president. Hunt quickly ended the interview.

On my radio program later that day, Karoline described what had happened. “I thought I was still on air,” she revealed. “I was going off about inflation and immigration and President Trump’s strategy for the debates,” she laughed, before adding that a producer had quickly piped in her ear and informed her that she’d been booted off the program. She’d kept her cool — and gone viral in the process.

She understands preparation as well. I’ve learned about it on the fly myself: I had to do a lot of homework on short-selling, fast, in January 2021 when the GameStop Reddit rally hit the news and my knowledge of short-selling was limited to what I’d seen in The Big Short years before. Karoline has had to be fast on her feet too, which will be key to managing press conferences and rapidly moving breaking-news issues. During her fill-in work on my program, it didn’t matter if the news of the day was something she’d been discussing for years or an outrageous new scandal like the cocaine found in the West Wing one afternoon; she was putting in the prep work before the on-air sign turned red.

A White House press secretary is expected to have clear answers on a host of different issues at any given moment. Understanding the importance of rigorous preparation is crucial when dealing with briefing room reporters, many of whom will, of course, go back to their hostile pre-Biden demeanor as soon as possible.

As Karoline stares out at these opportunistic self-identifying “journalists” trying to make a name for themselves, she’ll be in a position to outsmart them simply by outworking them.

Considering she was back on the campaign trail for Trump nine days after giving birth to her son, I doubt that will be an issue.

Donald Trump loves to quote Mike Tyson’s famous line regarding the best-laid plans: “Everyone has a plan until they get punched in the face.” I found that out during a segment years ago, when I made a throwaway comment about how I’m not a fan of beagles. Suddenly I was inundated with angry messages about beagles: why they are a wonderful breed of dog and why I am a big fat stupid idiot for suggesting otherwise. All my ideas for the segment were overwhelmed that day by Beaglemania — great radio, but I needed to be able to roll with it.

Karoline’s good at that: on the air one day she took a call from a man who insisted that he and his buddies had seen an alien while they were drinking late one night. It was a hilarious and bizarre phone call and most of the green-room team thought that Karoline, like most political squares, would hurriedly move on and pretend it never happened. Instead, she went with it, getting good radio out of the domino effect; soon callers were lined up for a chance to share their extraterrestrial anecdotes.

Leaning in, embracing change and not shying away from controversy will be indispensable in the White House. Things won’t always go as planned, but Karoline is calm, prepared and flexible. The same skills that helped her become an instant hit on the radio will serve her well behind a new microphone on the briefing room podium.

This article was originally published in The Spectator’s January 2025 World edition.