Cincinnati Men Once Sought Recognition As the City’s Homeliest

During the early 1910s, aspiring politicians argued that a homely appearance signaled honesty and relatability.
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Who is the homeliest man in Cincinnati? More importantly, why would anyone care? And yet, in 1910, that was not only a front-page question but became a matter of debate.

Harry Probasco

Cincinnati Post (1910), image extracted from microfilm by Greg Hand

The whole affair started when attorney Henry Russell “Harry” Probasco (benefactor of the famous statue on Fountain Square) tossed his hat in the ring as a candidate for the U.S. Senate from Ohio. This was back in the days when Senators were chosen by state legislatures, not by the voters directly.

The Ohio seat was held by Charles W. Dick of Akron, a man esteemed for his good looks and known as the “Akron Beauty.” Senator Dick’s looks were besmirched by a cloud of scandals, and a half-dozen Republican stalwarts had lined up to take his place in Washington. Referring to the senator’s shady reputation, Probasco decided to make his homely looks an asset in the campaign. He told The Cincinnati Post [January 19, 1910]:

“Yes, sir, they do say that I am the homeliest man in town. I AM homely and glad of it. There is some distinction as being known as the homeliest man in a city. If the proverb that ‘handsome is as handsome does’ is true, Senator Charles Dick is the homeliest man in the State.”

Judge James Swing

Centennial History of Cincinnati and Representative Citizens, Volume 2 (1904), digitized by the Public Library of Cincinnati & Hamilton County

Word got around, however, that Probasco didn’t really believe he was the homeliest man in Cincinnati. He let it slip that he considered Judge James B. Swing to actually hold that title. According to The Post [January 20, 1910]:

“That precipitated the war. All the homely men in town, who don’t care much about their looks anyhow, and each of whom claimed the championship of homeliness, have broken into the controversy.”

Leading the pack was Edward J. Dempsey, who had served as mayor of Cincinnati in 1906-07. According to The Post:

“Former Mayor Dempsey had thought all along that he had a chance some time to wrest the laurels from Probasco’s face.”

Mayor Edward Dempsey

Centennial History of Cincinnati and Representative Citizens, Volume 2 (1904), digitized by the Public Library of Cincinnati & Hamilton County

Although Dempsey was reported to be somewhat offended that his homely appearance wasn’t acknowledged, he refrained from public comment. Not so Judge Swing, who issued a public statement composed, according to The Post, “of caustic and sulfuric acid, as well as a liberal quantity of sour grapes.” His statement read:

“Mr. Probasco is all wrong. He is an exceedingly handsome man, despite his admission that he is homely. So, therefore, even if I am a homelier man than he, I cannot be so very homely at that. Mr. Probasco certainly is a beautiful man.”

No one appears to have agreed upon who was, in fact, officially the homeliest man in Cincinnati. Probasco exercised his rights to the unofficial title for some time, usually with an assist from The Post. When New York financier J. Pierpont Morgan arrived in Cincinnati to attend, of all things, an Episcopal church convention, the newspaper [October 5, 1910] promoted the hometown homely against Morgan’s legendarily dreadful physiognomy:

“[Morgan] is not even as good looking as Attorney Harry Probasco, of Cincinnati, who has admitted and is proud of the fact that he is the most homely man in Cincinnati.”

Probasco, sensing that his title might be in jeopardy, wrote a defense, published by The Post the next day:

“I hope you have not hurt Mr. Morgan’s feelings by publicly accusing him of being more homely than I am. Neither he nor I can dispute you, for we have not been profited by sight of each other. However the fact may be, our personal appearance, I am sure, has not been a total bar to our spiritual and material advancement.”

Whether it was his homely looks or not, Probasco lost out in his quest for the Senate. He came in dead last.

A few years later, a challenger for the homeliest crown emerged from New York. It was a temporary contest because Fred W. Ellsworth was only visiting while the American Institute of Banking held its national convention here. While in town, though, Ellsworth, who claimed to be the homeliest man in the U.S., had lots to say about homeliness. He certainly had the authority, since he served as president of the Homely Men’s Club of America. He told The Post [September 22, 1916] that the club had five classes of members:

“Elective and automatic members are admitted to our club without question. Unconscious members don’t want in, because they don’t know they are ugly. Involuntary members are elected whether they want to be or not, and mechanical members are those who are ugly because of some habitual twisting of the face.”

As obsessed as The Post was with homely men, it must have proved somewhat embarrassing in 1913 when the newspaper could not find a single homely man in town. The occasion was the newspaper’s annual outing to Chester Park. Among the many contests—including largest family, heaviest baby, and best waltzer—The Post offered a $5 prize for the homeliest man. Although the judges sat ready to award that sawbuck, not one single candidate showed up to stand for inspection.

The Cincinnati Enquirer [May 20, 1917] later opined:

“The homeliest man in the world is the handsomest man in the world to the woman he is good to.”

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