In the past, the term “milquetoast” was a name that would belittle the meek. And while it sounds like some sort of French bread dish (and that’s no coincidence), the term originated with an early 20th-century comic strip star named Caspar Milquetoast, who through the subtle brutalities of everyday life became a sort of hero for the timid soul.
The original milquetoast was the creation of the illustrator H.T. Webster. Known as “Webby” to his friends, Webster grew up in rural Wisconsin and started his cartooning career in the first decade of the 20th century, with little formal education. He drew sports cartoons for some newspapers out of Denver, Colorado, before moving back to Chicago, Illinois, where he’d briefly attended art school.
During his years in Chicago, Webster produced satirical political cartoons for papers such as the Chicago Inter Ocean, which proved incredibly popular. According to the introduction to 1953’s The Best of H.T. Webster (published a year after his death), Webster’s political cartoons were front-page attractions and even inspired an unsuccessful bill brought before the Illinois legislature to outlaw cartoonists’ unflattering portrayals of state senators and representatives.
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