“Love is the triumph of imagination over intelligence.”
— H. L. Mencken

The Sage of Baltimore. [Image courtesy: The American Mercury]
Mencken lived in the same house in the Union Square neighborhood of the city for all but 5 years of his life. At 9 he read Huckleberry Finn by Mark Twain and knew he wanted to become a writer. His family had other ideas.
He worked for 3 years at the family owned business and would have stayed indefinitely, but upon his father’s death in 1899 Mencken was “free to choose his own trade in the world.”His grandfather had prospered in the tobacco business and his father, August, continued the family tradition. Mencken studied at the Baltimore Polytechnic Institute (1892-96) and then worked at his father’s cigar factory. [Books and Writers]
Within a week, Mencken “invaded” the city room of the old Baltimore Morning Herald to face down the city editor and ask for a job…There were no jobs that day, but Mencken, persistent, returned daily for two weeks. “Finally I was sent out on a small assignment — it was a stable robbery at Govans — and a few days later I was on the staff,” [H.L. Mencken, Pioneer Journalist, By Jacques Kelly The Baltimore Sun]
His skill as a writer and his reputation for being able to turn a phrase grew. So 6 years later when the Herald closed its doors Mencken applied for a position at the larger Baltimore Sun. He started at “The Sun as its Sunday editor, became an editorial writer, and in 1911 started writing his own column, the Free Lance Mencken.” He worked at The Sun until 1948, bring his unflinching wit and critical eye to everything he saw.
“I believe that a young newspaper reporter in a big city… led a live that has never been matched… for romance and interest.” [Mencken from his only known audio interview. Courtesy of: The American Mercury.com]/

Mencken at work. [Image Courtesy: Enoch Pratt free Library Digital Collections.]
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