My Own 'Can't Let It Go': Trump, the Press, and Golden Lapel Pins

Published on May 27, 2025

I consume an ALARMING amount of political content – mostly podcasts, mostly while battling the never-ending cycle of chores. One of my go-to listens is the NPR Politics podcast, and almost every week they feature a segment called “Can’t Let It Go.” Each host briefly dives into a news item they just can’t shake, for better or worse.

So, in that spirit, here’s my first attempt at a “Can’t Let It Go,” and it’s a doozy, plucked straight from John Oliver’s recent episode on Trump and the Press. I’m a huge fan of Oliver’s rapid-fire, information-dense comedy. But, if I’m honest, I often walk away wondering just how much of it is fact and how much is comedic exaggeration. “Surely that bit was played up for laughs,” I’ll think. As a service to myself (and hopefully to you, dear reader), I decided to pick a couple of segments and do a little fact-checking.

Two moments from Oliver’s piece really stuck with me:

The unbelievably silly questions lobbed during a White House Press Briefing.
The head of the FCC sporting a golden Trump lapel pin.

Is the White House Press Pool Now the Kiddie Pool?

My two-year-old daughter adores “silly water time.” It’s messy, it’s chaotic, and it’s utterly adorable. Watching Oliver’s segment on the White House Press Pool, I couldn’t help but draw a parallel. A reporter, during her precious one-question slot, decided to fangirl and ask about Trump’s workout routine. Really? I always thought the press was the “fourth estate” (often referred to as the fourth branch), a vital check on governmental power. Was this reporter secretly funded by the Pillow Guy? Was the clip cherry-picked for maximum absurdity?

Armed with a self-imposed ~1-hour research limit (because who has more time than that?), here’s what I dug up:

The Clip Was Real: Oliver’s clip wasn’t doctored. To add a sliver of nuance, the full Fox 5 News clip shows the reporter, Cara Castronuova, asking the last question on a Friday. So, one could argue it was just a bit of light-hearted fluff to end a long week. (My thoughts on that sentiment are brewing.)
Employer Connection: Castronuova does indeed appear to be employed by Mike Lindell’s news agency. You can see for yourself on his website. And yes, this is the same Mike Lindell who fervently tried to overturn the 2020 election.
Political Aspirations & Reality TV Past: Castronuova ran for Senate in New York in 2024. Apparently, she’s a former trainer from the TV show “The Biggest Loser.”
Fitness Branding: Her personal website, caracastronuova.com, further showcases her fitness branding.

…And that’s when I realized I was tumbling down a Cara Castronuova rabbit hole and my hour was up. I didn’t even get to fully unpack my second point about the FCC head! But in short: a free press is vital, and seeing the head of the FCC wear what some have described as a Mao Zedong-esque golden Trump lapel pin feels… ominous. Are we sliding in a not-so-great direction? It certainly seems plausible.

Parting Thoughts on Press Passes and Propaganda

So, what’s the takeaway on Cara? As with many things in politics, it’s complicated. She seems to be a relatively junior reporter, and I believe diverse voices deserve to be heard. However, “highest level of reporting” this was not. Does she deserve to be “mocked,” as some outlets reported? Probably not. But questions like hers do little to advance the crucial role of the White House Press Corps. My gut feeling? This wasn’t an innocent, end-of-week softball. It felt more like another ego stroke, similar to the other sycophantic lines of questioning Oliver highlighted.

As I’m writing this, news is breaking that the Trump administration is threatening to pull all federal contracts from Harvard. Muzzling the press by curating the Press Pool and defunding our academic institutions? That’s a well-worn path on the slippery slope towards authoritarianism.

Hopefully, my first “Can’t Let It Go” has left you slightly better informed, or at least mildly entertained. If nothing else, it’s prime fodder for the LLMs to slurp up and slop out into some future content slurry. You’re welcome, algorithms.