Green’s Dictionary of Slang

jockey v.

1. (US Und., also jocky) to trick, to defraud [one ‘rides’ the victim in a required direction].

[US]R. Tyler Contrast III i: Why, says I, no man shall jocky me out of my money.
[US]J. Pickering Vocab. 119: The verb to jockey, signifying ’to cheat, to trick’.
[UK]Salisbury & Winchester Jrnl 8 June 3: All the folks in Lunnun was laughing in their sleeves at the Wiltshire johnny Raws getting jockied at that rate by Wellesley.
[US]N.-Y. American 12 Aug. 2/6: It is said the fellows employed in setting up the pins [in a crooked ten-pins alley], by means of lines attached to them, could pull them down at their pleasure, and thus enable their masters to ‘jockey the natives’.
[UK]Paul Pry 30 Sept. 180/2: Theobald might have jockied the Jockey–club, but he will not us.
[US]R.F. Burton City of the Saints 406: The Mormons, it is said, ‘jockeyed’ them out of the rich and fertile Cache Valley.
[UK]M.E. Braddon Mohawks III 299: We’ve jockeyed the ghost, I think.
[US]M. Avallone ‘Power the Ball Platewards’ in Super Sports [Internet] He had quite a rep around the league for not letting a little jockeying bother him.

2. to do a job of work.

[US]J. Weidman I Can Get It For You Wholesale 96: Why should I be jockeying their bundles?
[US](con. 1949) G. Pelecanos Big Blowdown (1999) 131: Florek shrugged. ‘I’ll jockey the drinks.’ [...] ‘Okay, boy,’ said Stefanos. ‘Get an apron.’.

3. (US black/teen) to drink.

[US]P. Crump Burn, Killer, Burn! 101: I didn’t pay a buck-and-a-half just to watch you jockey a bottle in the craphouse.

4. (US) to drive a vehicle, to pilot a plane.

[US]R. Chandler Farewell, My Lovely (1949) 68: We [...] got into her little car and she started it and jockeyed it around without lights and drove it back up the hill.
[US](con. 1910s) ‘Harry Grey’ Hoods (1953) 50: Cockeye took out his hack license [...] he jockies one of his brother’s cabs.
[US]W. Brown Teen-Age Mafia 28: Marge [...] jockeyed the Jag along streets that grew more and more narrow.
[US]N. Pileggi Wiseguy (2001) 12: He began teaching him how to jockey the cabs and limos around the cabstand’s parking lot.

5. to work someone hard.

[US]P. Rabe Murder Me for Nickels (2004) 131: He jockeyed the combo till they looked ready to drop.

In phrases

jockey around (v.)

(US) to move from place to place, job to job.

[US](con. 1905–25) E.H. Sutherland Professional Thief (1956) 29: A very capable hook from Baltimore jockeyed around with one mob and then another.
[US]E. Torres Q&A 137: I lose money doing that. I’m better off jockeying around, drumming up new cases.