Green’s Dictionary of Slang

high roller n.

[SE high + roller, a dice-player]

1. (orig. US, also big roller, heavy..., high thrower) one who spends extravagantly, one who gambles for high stakes.

[US]J. O’Connor Wanderings of a Vagabond 361: Some of the smaller players began to remonstrate about the price of the checks, which caused some spicy conversation between them and those who desired to be considered ‘heavy rollers’ to ensue.
[US]G. Devol Forty Years a Gambler 142: There was more money on board than I ever saw in my life before, and all the men were ‘high rollers’.
Nat. Police Gaz. 24 Nov. n.p.: [pic. caption] A Boston High Roller ‘On a Bat’ with a High Grade Dazzler.
[US]A.H. Lewis ‘Crime That Failed’ in Sandburrs 78: If we can bring him a tip or two [...] from one or two high rollers whose names goes, he’ll take it kindly.
[US]‘O. Henry’ Roads of Destiny 340: There comes in a party of these high-rollers that are always hunting up new places to eat in and poke fun at.
[US]Daily Trib. (Bismarck, N.D.) 16 Apr. 5/2: A hust [sic] like the stillness of death fell over that drunken crew of high rollers.
[US]S. Lewis Babbitt (1974) 153: He didn’t ‘care a fat hoot for all these highrollers’.
[US]W.M. Raine Cool Customer 47: He’s a bit of a high-roller, I’ve heard. Spends a good deal for a hundred fifty dollar a month teller.
[US]10 Story Western May 57/2: They were high rollers, playing for big stakes, and hang the poor devil who came out on the short end [DA].
[US]‘Toney Betts’ Across the Board 121: A card sharp who worked the ocean liners and was a high roller with the horses.
[US]T. Thackrey Gambling Secrets of Nick The Greek 19: These guys are real high rollers. Big!
[US]B. Hirschfeld Generation of Victors 274: The big rollers, they’ll go where the action is every time.
[US]G.V. Higgins Digger’s Game (1981) 8: All the high rollers going out to Vegas.
[US]J. Ellroy Brown’s Requiem 63: You get high-class putter jobs with gamblers and high rollers who know how to pay.
[US]S. Morgan Homeboy 270: Some men, highrollers usually, wanted the girls up in their hotel rooms.
[UK]M. Dibdin Thanksgiving 22: Like the casinos sending a private plane down to wherever to lure some high roller back to the tables.
[US]Mad mag. July 37: High rollers can’t not bite. Drives ’em nuts.

2. attrib. use of sense 1; also fig.

[US]A.H. Lewis ‘Mulberry Mary’ in Sandburrs 9: This Cleopatra was a wonder for looks. She was d’ high-roller tart of her time, an’ d’ beautifulest.
[US]D. Hecht Skull Session 451: He has high-roller spending habits.
[US]D. Winslow The Force [ebook] [T]he men in Madeleine’s black book—the high-roller businessmen, the politicians, the judges.

3. an attractive woman.

[Aus]Sun. Times (Perth) 10 July 4/8: I met a galaxy of girls, / ‘High-rollers’ each and all.

4. (US) God.

[US]C. Sandburg ‘Crapshooters’ in Smoke and Steel 34: God is Luck: Luck is God: we are all bones the High Thrower rolled: some are two spots, some double sixes.

5. (US) one who behaves outrageously.

[US]S. Lewis Main Street (1921) 389: Seems she was a teacher, but she certainly was a high-roller – O boy – high, wide, and fancy!

6. (US black, also high-roller hat) a type of hat worn by gamblers.

[US]A. Bontemps God Sends Sun. 24: I’s gonna git me a two-gallon high-roller hat. [Ibid.] 25: His high-roller had tiny naked women worked in eyelets in the crown.

7. (W.I./UK/US black teen) a materially successful person, usu. a rich ghetto drug dealer, as used by the Los Angeles gang, the Crips.

[US]J. Wambaugh Choirboys (1976) 171: He [...] let her support him and go down on lots of fat cats and high rollers for lots of money.
[US]Ice-T ‘High Rollers’ [lyrics] When I say High Rollers, I mean the best.
[US]L. Bing Do or Die (1992) xvi: The new dealer is a young black entrepreneur, and he is called either a high roller or a baller, depending on his gang allegiance.
[US]G. Sikes 8 Ball Chicks (1998) 13: Most gang members who sold drugs were not growing rich. Some dealt to help pay the rent [...] Few were high rollers.
[US]Source Aug. 168: But beyond all the slot machines and high rollers, Las Vegas is home to the Magic convention.

8. (US) a senior manager.

[US]B. Hamper Rivethead (1992) 174: One of the high rollers from Labor relations motioned my foreman into a glassed-in office.