Green’s Dictionary of Slang

gaycat n.

[ety. unknown; the best possibility is that senses 1 and 2 were often homosexual, and thus sense 4 which in turn may suggest a transitional point between SE gay, cheerful, and gay adj. (6); cit. 1934 in sense 3 may be voluntary self-censorship by Kuethe; note ‘The Kid’ who appears in the eponymous The Gay-cat (1921) is not openly homosexual, although this too may be contemporary self-censorship by the author]

1. (US tramp, also gay-catter) a young or inexperienced tramp.

[US]Century Mag. 47 n.p.: After Utica there 's Rochester, a place that oncet was good, but is n't worth pawnin' now since that gay-cat shot a woman there.
[US]J. Flynt Tramping with Tramps 13: Nothing arouses his scorn more than the dilettante, or ‘gay-cat,’ as he calls him.
[US]J. London Road 173: Gay-cats are short-horns, chechaquos, new chums, or tenderfeet. A gay-cat is a newcomer on The Road who is man-grown, or, at least, youth-grown.
[US]A. Berkman Prison Memoirs of an Anarchist (1926) 163: I ain’t no gaycat to work.
[US]D. Runyon ‘A Tale of two Fists’ VIII in Pittsburgh Press (PA) 30 Apr. 25/4: A ‘gaycat’ in the parlance of the road, is a ridiculous sort of individual who will stoop to work if he gets the slightest opportunity.
[US]G.H. Mullin Adventures of a Scholar Tramp 3: I was a gay cat, as the apprentice tramp is universally called.
‘Pine-Top’ Smith ‘Nobody Knows You When You’re Down & Out’ 🎵 Nobody don’t know you when you’re down and out / [...] / But as soon as you get on your feet, / A gang of gay-catters you sure can meet.
[US]Irwin Amer. Tramp and Und. Sl. 84: Gay Cat. – [...] a newcomer to tramp life, forced to work at times when unable, because of his inexperience, to live without.
[US]Goldin et al. DAUL 77/2: Gay-cat. (Hobo) An inexperienced hand, masquerading as a seasoned hobo.
[US]W. Burroughs Foreword in Black You Can’t Win (2000) 9: This young gay cat starts bad-mouthing Salt Chunk Mary and old George.

2. (US tramp, also cat) a hobo who only accepts occasional or seasonal work.

[US]J. Flynt Tramping with Tramps 104: The gay-cats are men who will work for ‘very good money,’ and are usually in the West in the autumn to take advantage of the high wages offered to laborers during the harvest season.
[US]‘Number 1500’ Life In Sing Sing 255: Gay Cat. A traveler; tramp on the move.
[US]Morn. Tulsa Dly World (OK) 13 June 19/2: Gay cat — A hobo [...] one who is too proud to work; goes from towen to town in search of work.
[US]Maines & Grant Wise-crack Dict. 9/1: Gay cat – Tramp who never works.
[US]G. Milburn Hobo’s Hornbook xix: To rid themselves of the last gay cats, the builders of railroad coaches have now but to heed the dying admonition of Jay Gould’s daughter.
[US]Irwin Amer. Tramp and Und. Sl. 48: Cat. – An itinerant worker. A person on the fringe of hobo, yegg or criminal groups, beating his way about the country and working at this or that as opportunity offers.
[US]Monteleone Criminal Sl. (rev. edn).

3. (US Und.) the junior member of a criminal gang, employed to run errands or spy out possible crimes.

[US]S.F. Chronicle 6 Mar. 3: At the next stopping place the ‘gay cat’ is put to work. He builds the shack or finds a deserted house where the gang may stop. He then visits the nearest town and buys canned goods and provisions. In short, he is the man-of-all-work and generally possesses an open countenance calculated to deceive.
[US]‘A-No. 1’ Mother of the Hoboes 44: The Rating Of The Tramps 39 Gay Cat: employed as scout by criminal tramps.
[US]N. Anderson Hobo 101: [From A No. 1, The Famous Tramp] 39. Gay Cat. Employed as scout by criminal tramps.
[US]J.L. Kuethe ‘Prison Parlance’ in AS IX:1 26: gay cat. A boy who acts as a runner for a gang.
[UK] (ref. to 1920s) L. Duncan Over the Wall 75: Our frequent sessions in stealing [...] were always prefaced by a thorough casing of the lay beforehand by our ‘gay cat’ cooking ‘soup’ out of eighty-per-cent dynamite.
[US]Monteleone Criminal Sl. (rev. edn).

4. (US tramp) a tramp or criminal’s younger, homosexual companion.

Salt Lake Teleg. (Salt lake City, UT) 27 Feb. 10/4: A ‘gay cat’ is a ‘yegg’s’ servant with no nerve for anything.
[US]P. & T. Casey Gay-cat 17: A gay-cat is the scorn of hoboes. He is a fake hobo. He lacks altogether the qualities of a blown-in-the-glass stiff. He will ‘peach’ on his mates. He will turn against a friend when that friend is down to tomato cans. Anything and everything mean and despicable is worthy of a gay-cat. To call a man that is to brand him with the most loathed name a hobo knows. It is the quintessence of contempt.
[US]C. Panzram Journal of Murder in Gaddis & Long (2002) 115: I have met every kind of a crook there is. [...] dingbats and gay-cats.
[US]Ersine Und. and Prison Sl.
[US]C.B. Davis Rebellion of Leo McGuire (1953) 3: Experience isn’t worth a gaycat’s poke unless you can interpret it.
[US]Goldin et al. DAUL 77/2: Gay-cat. (Hobo) [...] a boy, serving his hoboing apprenticeship, panhandling and stealing for veterans, often serving in a passively homosexual role.
[US]N. Tosches Where Dead Voices Gather (ms.) 256: In white hobo slang, going back to the late nineteenth century, the words denoted a lesser, inexperienced member of the tramp community, and in time came to imply homosexuality as well: a ‘gay cat’ being the punk-queer companion of an older, veteran hobo, synonymous with ‘gunsel,’ a Yiddish-derived pejorative epithet of like meaning [...] that had been a part of white criminal slang since the early years of the twentieth century.

5. (US Und.) a thief who only works when he needs money.

[US] ‘Und. and Its Vernacular’ in Clues mag. 158–62: gaycat Thief who steals only when necessity compels him to raise money.

6. (US Und.) a safebreaker.

[US]St Louis Post-Despatch 16 Jan. 25/2: First thing you know, you’ll take a harness bull for a gay cat and squeal all you know.
[US]C.S. Montanye ‘Perfect Crime’ in Penzler Pulp Fiction (2007) 351: He was a gay-cat, which means a blaster or a safe-blower.