Green’s Dictionary of Slang

high roller n.

[SE high + roller, a dice-player]

1. [late 19C+] (orig. US, also big roller, heavy..., high thrower) one who spends extravagantly, one who gambles for high stakes.

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

3. an attractive woman.

4. [1920s] (US) God.

5. [1920s] (US) one who behaves outrageously.

6. [1930s] (US black, also high-roller hat) a type of hat worn by gamblers.

7. [1980s+] (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.

8. [1990s+] (US) a senior manager.