Sean Naylor

Washington, D.C.

Author and Freelance Reporter at Freelance

Co-founder of The High Side. Author of Relentless Strike - The Secret History of Joint Special Operations Command: https://t.co/lEOTReZt55. RTs are not endorsements.

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Articles

The High Side

1 week ago | thehighside.substack.com | Sean Naylor

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4/6/25 National Security News and Commentary

3 weeks ago | myemail.constantcontact.com | Lingling Wei |David Averre |Sean Naylor |Chris Wadsworth

Quotes of the Day:“Laws which prescribe what everyone must believe, and forbid, meant to say, or write anything against this, or that opinion, are often pass to gratify, or rather to appease the anger of those who cannot abide independent mines.”– Baruch Spinosa. “For every complex problem there is an answer that is clear, simple, and wrong.”- H. L. Mencken“A man is like a fraction who's numerator is what he is, and who's denominator is what he thinks of himself.
March/April 2025

3 weeks ago | airandspaceforces.com | Sean Naylor |Heather Penney |Tobias Naegele |John Tirpak
Battle of Takur Ghar Controversy Continues | Air & Space Forces Magazine

3 weeks ago | airandspaceforces.com | Sean Naylor

Air Force Tech. Sgt. John Chapman's heroism at the Battle of Takur Ghar in Afghanistan on March 4, 2002, earned him a posthumous Medal of Honor, only the 19th awarded to an Airman since the service’s founding in 1947. USAF Photo Caption & Credits Twenty-three years after his heroic death on a frozen Afghan peak, John Chapman is still fighting against the odds.
Speakers at SOF conference tiptoe around Trump on Ukraine, allies

2 months ago | thehighside.substack.com | Sean Naylor

President Donald Trump was the “elephant in the room” at a Feb. 20 Washington special operations conference, as numerous speakers implicitly questioned his policies, but without mentioning him by name.
Sean's guest appearance on The Danny Jones Podcast

Jan 15, 2025 | thehighside.substack.com | Sean Naylor

While down in Tampa for the annual SOF Week convention last week, I took the opportunity to head across Old Tampa Bay to a studio in Seminole to record an appearance on The Danny Jones Podcast. Even though (or perhaps because) it’s not a pure national security show, I found the experience thoroughly enjoyable. It’s always a good idea to step outside one’s comfort zone and get a sense of how non-natsec professionals react to one’s work - what they think is interesting, and what it means.
Men under "downward pressure"

Oct 31, 2024 | thehighside.substack.com | Sean Naylor

What follows is a very lightly edited transcript of an exclusive interview with Maj. Gen. Jason Slider, head of the U.S. Army’s John F. Kennedy Special Warfare Center and School (or SWCS – pronounced “swick” – for short), and CSM Lionel “Lee” Strong, the center’s senior enlisted adviser. The High Side’s Sean D. Naylor conducted the interview on Oct. 15 in Washington, D.C., during the annual meeting of the Association of the U.S. Army.
Two new jobs, but too few people (and robots)

Oct 29, 2024 | thehighside.substack.com | Sean Naylor

Army special operations leaders are pushing for two new jobs in Special Forces formations: one to call in artillery and air strikes and another to handle robotics and other automated systems. There are just two problems: They are critically short of both people and robots.
In The Kill Zone: The Life and Times of Willie Merkerson (Part 7)

Sep 13, 2024 | thehighside.substack.com | Sean Naylor

The flatbed truck raced toward the Khartoum airport tarmac just as the hulking U.S. Air Force cargo jet touched down and slowed to a stop. With the aircraft engines still running, the truck backed up to the paratroop jump door on the side of the plane. The CIA officers on the vehicle scrambled to unload four large wooden boxes from the back of the truck into the jet. Covered in the bright orange packaging used for diplomatic mail, each box was just big enough to fit a grown man inside.
In The Kill Zone: The Life and Times of Willie Merkerson (Part 6)

Aug 27, 2024 | thehighside.substack.com | Sean Naylor

One April evening in 1985, Milt Bearden, the CIA’s Sudan station chief, answered the doorbell at his Khartoum home to find on his doorstep two Israelis who were remarkably calm given their predicament. The pair, together with a third officer who arrived later that night, had been operating under non-official cover for the Mossad, the Israeli intelligence service.