Green’s Dictionary of Slang

gypsy n.

(US)

1. an independent trucker or the truck they own.

[US]Berrey & Van den Bark Amer. Thes. Sl. (2nd edn).
[US] AS XXXV:3 240: In truckers’ language a ‘gypsy’ is an owner-driven truck.
[NZ]McGill Reed Dict. of N.Z. Sl. 95: gypsy Housetrucker. 1990s.

2. a prostitute who travels around for trade or lives in a trailer park.

[[US]N. Pepper in Indianapolis Star 12 Dec. pt 4 22/6: G.I. Gypsy — a smooth girl].
[US]Maledicta IX 150: The original argot of prostitution includes some words and phrases which have gained wider currency and some which have not […] gypsies (traveling or trailer broads).

3. (US black) a promiscuous woman.

[US]U. Hannerz Soulside 99: [T]he streetcorner men who affirm their own natural tendency toward promiscuity often talk about whatever they see as female infidelity in moral terms. ‘That bitch is a gypsy, that’s all she is’ .

4. used in a variety of combs. (see below), usu. stereotyping Romanies as untrustworthy.

In compounds

gypsy gawn (n.)

(UK Und.) a ring with a diamond inset.

[Ire]Eve. Herald (Dublin) 9 Dec. 4/6: A ‘screwsman’ going to his ‘fence’ would inquire ‘What price a pair of “gypsy gauns,” a “red kettle,” a “white kettle,” a “Newgate tackle” and a “prop”. The ‘screwsman’ is asking what the ‘fence’ will pay for two single stone diamond rings, a gold watch, a silver watch, , or gold watch and chain and a tiepin.
gypsy’s deal (n.)

(US) a business deal that never actually materializes.

Anvil ‘Racial Hostility’ 🎵 on Plugged In Permanent [album] Have you heard that Spics will steal / Japs are sneaks, a Gypsy’s deal.
gypsy’s leave (n.)

departure without warning and without settling one’s debts.

[US]Maledicta III:2 160: gypsy’s leave n Departure without warning or settling of one’s debts; from the Gypsy’s nomadic habits.
gypsy’s warning (n.)

see separate entry.

gypsy switch (n.)

(US Und.) a form of criminal sleight of hand in which a high-denomination note is palmed and swapped for a low-denomination one.

[US]N. Algren Walk on the Wild Side 194: It’s a little matter of a bill that went into your hand a C note and came back to me as a ten spot [...] it was you pulled the gypsy switch on your best, your only friend.