This Memorial Day, I'm Thinking About Andy O'Keeffe — And About Starting Fresh
We honor our heroes, by their memory, and by not giving up.
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Today is Memorial Day, and I want to be honest with you about how I experience it — because I don’t think I experience it quite the way the greeting cards suggest.
It’s not a day of parades for me, at least not at first. It’s a day where I wake up and specific faces come to mind. Guys I flew with. Guys who were the best of us. Guys who are gone.
This year, I want to dedicate this day to one of them.
Capt. Andreas O’Keeffe was 37 years old when he died on March 15, 2018, in the skies over western Iraq. His HH-60G Pave Hawk helicopter — carrying seven airmen total — went down near the city of Al-Qa’im in Anbar province. There was no enemy fire. Some crashes just happen. That’s one of the cruelest truths of flying in a war zone.
I knew Andy from his time flying the RC-26B — the same platform I flew. The RC-26B is an intelligence, surveillance, and reconnaissance aircraft. You spend a lot of hours up there watching, waiting, tracking. It demands patience and precision. Andy had both. He flew with the 174th Attack Wing out of Hancock Field in Syracuse before transitioning to the 106th Rescue Wing in Westhampton Beach, New York, where he became an HH-60G Pave Hawk pilot with the 101st Rescue Squadron.
Let that career arc sink in for a second. He went from ISR work to rescue work. He chose to put himself in the most dangerous situations — not just flying into combat, but flying into combat specifically to save other people’s lives. He had deployed to Iraq three times by the time he died. He’d been to Afghanistan. The Horn of Africa. He flew Hurricane Harvey relief missions in Texas. He was the kind of guy who shows up everywhere something needs to be done.
He was one of seven airmen killed that day. His hometown of Center Moriches, New York dedicated a street sign to him in 2022 — the corner of Anderson Street and Winnie Road. That’s what we give the best among us. A sign on a street corner. It’s not enough. It never is. But we do it because we need to mark the space where a good man used to be.
I miss Andy. I miss all of them.
Here’s the thing about Memorial Day that I’ve wrestled with for years, and I want to say it plainly: it has to be both things at once.
It has to be somber. It must be. If you didn’t feel a weight this weekend — if it was just mattress sales and barbecues — then we’ve lost the thread entirely. The weight is the whole point. The weight is how we carry them with us.
But it also has to be a day of happiness and celebration. Because if it isn’t — if we don’t insist on that too — then what exactly were Andy and the others fighting for? What was the point of any of it?
They weren’t fighting so we could feel sad once a year. They were fighting so kids could run around in backyards, so families could sit together, so we could argue about politics and watch sports and live our ordinary, remarkable lives without the fear that comes with being unprotected. The joy of this weekend is the whole justification for the sacrifice. To deny yourself that joy out of guilt is, I’d argue, its own kind of disrespect to the fallen.
So yes — grieve. And then go be alive, loudly and gratefully, because that’s what they bought.
My generation — the post-9/11 generation of service members — carried something heavy that I don’t think the country fully understands even now. We volunteered after the towers fell. We knew what we were signing up for. We went again and again. Some of us lost friends on the first tour and went back for a second one.
And the honest truth — the one that costs something to say out loud — is that not all of it was worth what it cost.
I believe that. I’ve believed it for a long time. The wars were long. The strategy was imperfect. The politics were messy. And some of the price paid was too high for what we got.
But I want to push back on the idea that it was all for nothing. Iraq is in a better place today because of American involvement. That took decades to shake out, and it wasn’t a clean or pretty process — it was brutal and costly and filled with mistakes. But the country has a government. There are elections. Civil society exists. The worst of what could have been — a permanent failed state, a regional catastrophe — didn’t happen. That is something. It doesn’t erase the grief, but it’s something real.
What I do struggle with — and I think many veterans struggle with — is Afghanistan. The moral injury there runs deep, and it’s bipartisan in its origins. The Trump administration negotiated the Doha Agreement in 2020, cutting a deal with the Taliban while essentially sidelining the Afghan government. It set a conditions calendar that stripped our leverage and telegraphed the exit. Then the Biden administration inherited that deal and executed the withdrawal in a way that was, by almost any honest accounting, a catastrophe. The images from Kabul — the desperation, the chaos, the people we left behind — those images live in a lot of people who served there.
That’s a wound that doesn’t have a clean answer. It was a bipartisan failure that spanned administrations, and both sides own a piece of it. I say that not to relitigate policy, but because on Memorial Day especially, we owe it to the men and women who served there to be honest about what happened.
We carry them by telling the truth.
Part Two: Let’s Start Over
Okay. Shift gears with me for a minute.
One of the things I think about when I have time to breathe — and Memorial Day weekend, ideally, is some of that time — is how trapped we’ve become in our own thinking. Both sides. All of us.
We arrive at our political positions through a mix of upbringing, experience, media diet, and tribe. And then we defend those positions with everything we have, not always because we’ve thought them through from scratch, but because they’re ours now. They’re part of our identity. Changing them feels like a betrayal.
What if we tried something different?
Here’s my challenge — for myself and for you: Imagine, just for a moment, that you could delete everything you already believe about how to solve America’s problems. No prior commitments, no team loyalties, no reflexive positions. You’re looking at the problems fresh, like a new set of eyes, and you’re asking: what would actually work?
I find this exercise clarifying in ways I didn’t expect, because it starts revealing something important: both sides can be right, depending on the circumstances.
Take taxes. When an economy is stagnant and capital is sitting idle, tax cuts can be exactly the right medicine — they stimulate investment, create incentives, get things moving. That’s not ideology, that’s just economics in a particular context. But take a different economic moment — say, one where the economy is humming along and the gap between the wealthy and everyone else is stratospherically wide — and the calculus flips. Now tax increases on the wealthy aren’t punitive. They’re how you fund the infrastructure and social capital that keeps the whole system healthy. Same policy lever, opposite correct answer, depending on the reality in front of you.
We’ve forgotten how to think this way. We’ve turned every policy question into a loyalty test.
So I want to ask you — genuinely, not rhetorically — what are the problems you think need a fresh set of eyes? What are the issues where you’ve noticed that your own side seems stuck in a loop, or where the other side is occasionally saying something that, if you’re being honest with yourself, is actually right?
Here are a few I keep coming back to:
Healthcare. Both the “free market fixes everything” crowd and the “single payer or bust” crowd have been arguing the same positions for thirty years. Meanwhile, Americans pay more and get worse outcomes than most of the developed world. What if we stopped asking “which team wins” and started asking “what actually works, and where do we have evidence for it?”
The national debt. Conservatives talk about fiscal responsibility and then pass massive tax cuts. Liberals talk about investment and then resist any discussion of entitlement reform. The number is real. Ignoring it is bipartisan and irresponsible. What’s the honest answer that neither side wants to say?
Criminal justice. The “tough on crime” approach of prior decades demonstrably failed by many metrics. But some of the overcorrection in recent years produced its own problems. What does evidence-based public safety actually look like, stripped of the culture war noise?
Immigration. We have an immigration system that everyone agrees is broken and almost no one wants to actually fix, because fixing it requires giving both sides something they don’t want to give. What’s the deal that actually works?
I don’t have all the answers on any of these. What I do believe is that the way we’re going about it — screaming across a chasm, checking the team scoreboard — isn’t getting us there.
This week, while you’re sitting with the people you love, or back at work, or volunteering, maybe take a few minutes and ask yourself: what do I actually believe, if I’m starting from scratch? What problem would I solve differently if I didn’t have to wear a jersey?
I’d love to hear your answers. Drop them in the comments. I mean it.
Today I’m raising a glass to Andy O’Keeffe, and to all of them.
The best thing we can do for them is stay honest, stay engaged, and not give up on this country they gave so much to protect.
Happy Memorial Day.
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