5 Years Later: Courage Is Still Rare

From my break with Trump to Kamala Harris’ blunt truths, the test remains: who will speak up, and who will stay silent?”

(A picture I took of the West Wing the day I chose to resign.)

Five years ago this week, I made the hardest decision of my career. Not only had I recently walked away from my job in the Trump White House and from my national security career, I went public with what I knew: that Donald Trump was unfit for office, and that his recklessness put our nation and lives at risk.

I knew the moment I spoke out, my life would never be the same. I wasn’t naïve about what would come next: the loss of my career in national security as well as in Republican politics, the smears on my character, the threats that would arrive in my inbox and follow me into my daily life. What I didn’t fully know was how much I would gain, too. The ability to finally tell the truth, to speak without fear, and to stand on the right side of history, even if it meant standing there alone.

The truth is, it wasn’t just a career move. It was a personal implosion. Everything I had built for years, the networks, the loyalty, the reputation within my circles and my political party, vanished overnight. Friends I had trusted disappeared. Others chose silence. Some of them slowly surfaced along the way, but then ran scared again when Trump returned to the Oval Office. And yet, in that silence, I found clarity. If people abandoned me because I told the truth, they weren’t really in my corner to begin with.

In the five years since, nearly everything I warned about when it came to Trump and his MAGA Project 2025 agenda has come to pass. The chaos, the corruption, the authoritarian instincts, the contempt for his enemies, and the glaring disconnect between the policies Trump boasts about and their damaging impact on working-class families like the one I was raised in, the very people he claims to represent. It wasn’t hyperbole. It was the reality I witnessed up close, day after day, in rooms where decisions about life and death, security and freedom, were treated as theater. Today, we are all living with the consequences of ignoring those warnings.

I think about the moments when I sat with the weight of my choice. I remember the quiet car rides home where I wondered how I would rebuild a career, or whether I’d even be able to walk into a grocery store without looking over my shoulder. I recall the conversations with my family, the fear in their voices, yet also their unwavering support. And I remember the day I finally put my name to my statement, knowing there was no going back.

I don’t regret my choice for one second. Morally, it was the only path forward. It wasn’t easy then, and it isn’t easy now. But the truth rarely is. Five years later, I stand by every word I’ve spoken—and the concerns I raised then are the same ones I warn about today, with even greater consequences given that these individuals are back in power. That’s why I remain committed to countering far-right extremism in every way I can.

And yet, I sit in rooms today with CEOs and figures from some of the largest media networks, people running the most powerful companies in America or anchoring major shows on television, who whisper the same truths I’ve said out loud over the past five years. They know Trump is bad for business, bad for stability, bad for America’s standing in the world. They’ll say it privately, off the record, sometimes even with a hint of relief that someone else dared to say it first. But when it comes to saying it publicly? Silence.

Some even tell me how much they admire my courage, but in the same breath, they admit they could never hire me, or even have me on their shows. And that’s after I spent the past five years appearing nonstop across networks for free, raising alarms about what was coming. Now, suddenly, with a few rare exceptions, they’re scared. They worry the Trump team will come after them. That fear is the point: the Trump team knows it, feeds off it, and weaponizes it through endless lawfare. Trust me, I’m still living that reality as a constant target of their litigation.

As a recent Yale CEO forum revealed, the reality is undeniable: Trump’s tariffs are damaging businesses, investment is frozen, inflation is up, and uncertainty is strangling growth. CEOs know this is unsustainable. They know it’s a house of cards. But they are afraid of the social media posts, the tantrums, the government retribution. So they bite their tongues.

Kamala Harris called this out bluntly in her first major interview since leaving office. On Rachel Maddow’s show, she described these business leaders as “feckless” for failing to stand up to Trump. She reminded them, and all of us, that democracy sustains capitalism, not the other way around. Without the rule of law, independent institutions, and freedom of expression, there is no foundation for the market on which they rely. That’s not a safe move, given how much influence corporate leaders have. She labeled Trump a tyrant, not watered-down language, at a time when many still try to dodge plain words. The candidate I saw then was the real deal, and I’m glad she’s now choosing to speak openly about what she faced during those 107 days. She didn’t just take aim at Trump; she also admitted to her own second-guessing and mistakes. Owning your own missteps publicly is rare in politics. And I saw firsthand how she navigated pressure, backlash, and an uphill fight while refusing to sugarcoat the stakes.

Courage, political courage especially, is rare. And when it shows up, whether in her words or in the choices of anyone willing to speak the truth, we should recognize it. I'll have more to say about this in the future, especially regarding what I witnessed as a Republican serving as a surrogate for Harris in her 2024 campaign, and the lessons I hope the Democratic Party learns as it moves forward. I am proud to have supported her, and I want to be very clear that I have absolutely no regrets.

This moment, five years later, is not about me. It’s about us. It’s about whether we are willing to confront hard truths, hold leaders accountable, and defend our freedoms even when it comes at personal cost. It’s about whether we let fear dictate our choices, or whether we remember that silence in the face of danger only empowers those who abuse power.

Five years ago, I made my choice. Kamala Harris has made hers. The question is: when will America’s business leaders make theirs? And more importantly, what choice will each of us make now in a world where comedians, academics, journalists, and everyday people are being silenced. We just saw this with the return of Jimmy Kimmel’s show (despite what networks are doing to block him from being shown on local channels), that your voices made a difference.

Silence may invite darkness, but your voices, joined together, can keep the light alive.

Thank you for walking with me on this journey, and for supporting me through it. If you're new to my story and my work, welcome. I'm glad you're here. I hope you keep an open mind, stay engaged, and join me in building the kind of future that's worth fighting for.

-Olivia