Who was the First Masshole?

Who was the First Masshole?

July 30, 2026 · 28 min

About this episode

Billy Baker and Emily Sweeney explore the origins of the term 'Masshole' and its cultural significance in Boston.

Who was the first Masshole? It’s a question that dogged Boston Globe feature writer Billy Baker, resulting in some serious research. This week on Say More, Billy comes on the show with Globe reporter Emily Sweeney to discuss the origins and deeper meaning of the phrase. They discuss their Boston childhoods, the fading Boston accent, and how Good Will Hunting changed South Boston forever. Email us at saymore@globe.com.

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Guests: Billy Baker, Emily Sweeney

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Organizations: Boston Globe

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