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I've begun reading the introduction to Best of H.T. Webster on Archive.org and came across this paragraph on page 9:

Webby had not yet reached his teens when the family moved to a small Wisconsin town which rejoiced (and still does) in the name of Tomahawk. George Ade said it was once on the map in pencil, but "some fresh drummer rubbed it out."

The book, including the dedication from which the paragraph was taken, dates to 1953. I cannot find a source for the quote in question, but Wikipedia says Ade was a writer from 1890 possibly up to his death in 1944, although I haven't researched this in depth.

Several online dictionaries have a definition for 'drummer' as a traveling salesman, so I'm assuming a "fresh drummer" would be a traveling salesman who's new to the profession. But I feel like I'm missing some context: why would such a person erase a town name from a map? Am I completely up the wrong tree?

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    Maybe because it was a bad prospect for a salesman: not enough residents to support the out-of-the-way trip, or maybe they had just been treated badly by the locals...you have to put yourself in the mind-set of the times. There was a story more or less along these lines about a salesman being pursued by townsfolk over a "mad-dog" hysteria. I think it even became a Twilight Zone episode. Jun 10, 2019 at 21:14

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Webby had not yet reached his teens when the family moved to a small Wisconsin town which rejoiced (and still does) in the name of Tomahawk. George Ade said it was once on the map in pencil, but "some fresh drummer rubbed it out."

Given the context - a light-hearted introduction to a book of cartoons and the meaning of "drummer":

(OED

3.a. colloquial (chiefly U.S. and Australian). A person who solicits custom or orders; a travelling sales representative. Also drummer-up. Cf. drum v.1 7b(a), to drum up 1a at drum v.1 Phrasal verbs. Now somewhat rare.

1833 Constellation (N.Y.) 8 June 308/1 The drummers, who have distinguished themselves in this Commercial Emporium the present season.

2001 N.Y. Times (National ed.) 1 Oct. b8/3 The invincible American drummer is back, resuming his sales route with welcome boorishness.)

I would assume that the salesman rubbed the town's name out as it was so small, and the people so boring and unexcitable, that it was not worth his (or any other drummer's) time in going there in order to sell his goods.

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George Ade also uses the expression "fresh drummer" in "The Fable of The General Manager of the Love Affair Who Demanded a Furlough," in Forty Modern Fables (1901):

"... If Cupid had his Way, every Marriage Service would be enacted in the still Moonlight, with no $10 Preacher to give the Cues, and only the Peeping Stars as Witnesses. The Young Couple would repair at once to a Lodge in some Vast Wilderness, eighty-five Miles from a Hotel Clerk or a Fresh Drummer. But as I am telling you., Love has no Voice during the so-called Festivities. When you begin to Frost the Cakes and hang Smilax on the Chandeliers, I [Cupid] fly the Coop."

According to James Maitland, The American Slang Dictionary (1891), fresh had the following slang meanings in the late 1800s:

Fresh, slightly intoxicated.

Fresh (Am[erican]), said of a man who thinks he knows everything and who talks freely and pushes himself forward.

and drummer had this meaning:

Drummer (Am[erican]), a commercial traveler.

J.S.Farmer & W.E. Henley, Slang and Its Analogues Past and Present (1891 & 1893) offers similar assessments of the two words;

Drummer, subs. ... 3. (general).—A commercial traveler; also AMBASSADOR OF COMMERCE or BAGMAN ... {Cf. DRUM = a road; and old-time pedlars announcing themselves by beating a drum at the town's end.} [Latest cited example:] 1885. G.A. Sala, Daily Telegraph, 14 August, 5, 3. Among whom were conspicuous sundry drummers or representatives of American commercial firms, bound for Australasia, there to push their wares.

Fresh, adj. ... 3. (Old English and modern American).—Inexperienced, but conceited and presumptuous ; hence, forward, impudent.

It thus appears that by "some fresh drummer rubbed it [the town name of Tomahawk, Wisconsin] out," Ade meant something like "an impudent traveling salesman single-handedly erased the town's name from the map (where it had been scarcely recognized by the wider world on account of its insignificance)"—the implication being that the place was so innocuous that no one would have noticed if someone had come along and reported, as a joke, that it didn't exist.

Apparently, for Ade, a "fresh drummer" was a byword for the sort of arrogant blowhard who could ruin a honeymoon just by being within 85 miles of it or who could take it upon himself to erase a tiny town from the map on a whim.

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