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Free Love, Fraud & Sawmills: The Wild Life of Henry Yesler

 The Scandalous Life of Henry Yesler: Seattle’s Rogue Founding Father


Things were rough in 1850's Seattle. Your toilet might explode after all

What does it take to build a city? Vision, ambition, or maybe a touch of audacity? Henry Yesler had all three—and then some. Known as one of Seattle’s founding fathers, his legacy is as colorful as it is controversial. From free-love philosophies to dubious business schemes, Yesler’s life was anything but ordinary.


The Builder of Seattle’s Fortune 

Henry Yesler arrived in Seattle with big plans. In 1853, he opened the city’s first steam-powered sawmill, transforming a muddy frontier into a thriving hub of industry. His sawdust even became the foundation for the city’s streets, giving rise to the term “Skid Road.” But behind his success lay a trail of unpaid debts and legal battles.


A Lottery Too Good to Be True

 Yesler’s knack for schemes hit its peak with his infamous lottery. Promising grand prizes like his sawmill and wharf, he sold tickets for $5 each (equivalent to $148 today). The catch? None of the funds went to the advertised project, and Yesler walked away with only a slap on the wrist.

Love, Scandal, and a 24-Year-Old Bride

Yesler’s personal life was just as scandalous. From his free-love lifestyle to marrying his 24-year-old cousin at the age of 70 (ish?), he kept Seattle’s gossip mill churning. Even in death, his estate was a whirlwind of destroyed wills and court battles.


Henry Yesler’s life serves as a reminder that ambition often comes with controversy. While his contributions to Seattle are undeniable, so are the lessons of accountability and ethical leadership.


Love a good scandal? Tune into the full episode of Rainy Day Rabbit Holes for more jaw-dropping tales about Henry Yesler and Seattle’s wild beginnings.


Keywords: Seattle history, Henry Yesler, Pacific Northwest, founding fathers, free love movement, Skid Row origins




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