high roll, v. — Green’s Dictionary of Slang

high roll v.

(orig. US)

1. (US) heavy betting.

1900

Nat. Police Gaz. (NY) 6/4: Sam had won back the $12,000, and $20,000 besides [...] in less than five hours, or an average of abou t $100 a minute, which will probably stand as a record lor high rolling for some years.

2. to spend money freely; to live hedonistically; also attrib.

1903		A. Binstead Pitcher in Paradise 66: The unfitness of Fred Barrett [...] had less to do with mere adiposity than high rolling.
1975		E. Torres Carlito’s Way 29: highrolling When you’re highrollin’ in the bread you’re bound to be out there jumpin’ come midnight.
1990		S. Morgan Homeboy 5: A faint familiar scent Rings remembered from some highrolling trick.

3. to act boldly or aggressively.

1902

Ade Forty Modern Fables 293: He had Grubbed along all his Life. In his Youth he never had gone High Rolling.

In derivatives

high-rolling (adj.)

aristocratic.

1909

H. Green Mr. Jackson 131: I’ve had my little experiences with [women], not o’ course with no swells from the high rollin’ mob, but wimmen ain’t much different.