Ep. 24 | Pappy Boyington and the Black Sheep Squadron : WWII's Greatest Misfits episode artwork

EPISODE · Apr 28, 2026 · 26 MIN

Ep. 24 | Pappy Boyington and the Black Sheep Squadron : WWII's Greatest Misfits

from Archives and Anchovies · host James Kulon

What do you get when you take a broke, debt-ridden, twice-divorced brawler with a drinking problem and hand him a pile of pilots nobody else wanted? Apparently, one of the most effective fighter squadrons of World War II.In this episode, we dig into the wild, complicated, and genuinely unhinged story of Major Gregory “Pappy” Boyington and VMF-214 — the Black Sheep Squadron. Assembled in two weeks from spare pilots and leftover planes, the Black Sheep flew some of the most intense combat missions of the Pacific War, racked up a staggering kill count, and did it all under a commanding officer who was simultaneously a combat genius and a complete personal catastrophe.We cover Boyington’s time with the Flying Tigers, the birth of the Black Sheep, the dogfights over Rabaul, his capture by the Japanese, his Medal of Honor, a memoir that angered half his former pilots, and a TV show that took considerable liberties with basically everything.History, humor, and one very complicated war hero.

What do you get when you take a broke, debt-ridden, twice-divorced brawler with a drinking problem and hand him a pile of pilots nobody else wanted? Apparently, one of the most effective fighter squadrons of World War II.In this episode, we dig into the wild, complicated, and genuinely unhinged story of Major Gregory “Pappy” Boyington and VMF-214 — the Black Sheep Squadron. Assembled in two weeks from spare pilots and leftover planes, the Black Sheep flew some of the most intense combat missions of the Pacific War, racked up a staggering kill count, and did it all under a commanding officer who was simultaneously a combat genius and a complete personal catastrophe.We cover Boyington’s time with the Flying Tigers, the birth of the Black Sheep, the dogfights over Rabaul, his capture by the Japanese, his Medal of Honor, a memoir that angered half his former pilots, and a TV show that took considerable liberties with basically everything.History, humor, and one very complicated war hero.

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Ep. 24 | Pappy Boyington and the Black Sheep Squadron : WWII's Greatest Misfits

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This episode was published on April 28, 2026.

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What do you get when you take a broke, debt-ridden, twice-divorced brawler with a drinking problem and hand him a pile of pilots nobody else wanted? Apparently, one of the most effective fighter squadrons of World War II.In this episode, we dig into...

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