Brian D. O'Leary

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Tuesday, March 10, 2026

O’Leary interviewed on “Finding Freedom”

In late December, I joined John Odermatt on Finding Freedom for a long-form conversation that hits the core of what I’ve been writing about: power, justice, and why trust in our institutions is collapsing.
If you’ve enjoyed my work, or even if you hate it, this interview is one of the clearest windows into how I think about the mess we’re living through, and what, if anything, we can do about it.

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Projecting Power, Abandoning Home

Many are asking about the recent military intervention into Venezuela to extract its president, his wife, and bring them to “justice” stateside: What kind of precedent does this set?

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R.I.P. Lenny Wilkens

The “dragonslayer” of the hardwood Basketball Hall of Famer Lenny Wilkens passed away on November 9, 2025, at the age of 88. We’ve written about Wilkens a few times here at The O’Leary Review. What follows is a newer draft of a column originally published earlier this year. May 25, 2025 In an age where spectacle passes …

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You Paid for the Truth …

Here’s Your UNRELENTING Collection. The 56-page online magazine is ready for you (Paid Subscribers Only) I come bearing gifts today. This one’s for you. As a paid subscriber to The O’Leary Review, you understand what it costs to cut through the noise—literally. You’ve invested in the work because you know what’s at stake and you’re tired of comfortable …

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From the Archives: Health Insurance

The Portland I Left Behind, The Healthcare Debate That Never EndedRepublishing My 2009 Oregonian Column I was digging through my archives earlier today, and to my surprise, I came across the column that follows this introduction. Sixteen years ago today, The Oregonian published my guest column on healthcare reform. I lived in Portland then. It is my …

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The Western that launched the British Invasion

A single phrase from John Wayne’s 1956 Western masterpiece traveled from Monument Valley to Liverpool, inadvertently launching the most influential rock ‘n’ roll band in history In 2008, the American Film Institute (AFI) named The Searchers (1956), starring John Wayne and directed by John Ford, the greatest American Western. It also ranks 12th on AFI’s list of …

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He Became President Thanks to Baseball

Before Ronald Reagan saved the free world from Soviet nuclear annihilation, he was a $75-per-week radio announcer recreating Cubs games hundreds of miles from Wrigley Field For those who grew up in the 1980s and 1990s, Harry Caray was synonymous with the Chicago Cubs. He was the Chicago National League Ballclub’s television voice on the …

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