Dictionary.com
Thesaurus.com
Showing results for high-rolling. Search instead for highrolling.

high-rolling

American  
[hahy-roh-ling] / ˈhaɪˈroʊ lɪŋ /

adjective

Informal.
  1. gambling, spending, or living extravagantly or recklessly.

    high-rolling gamblers; a high-rolling investor.


Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

In recent years, Beijing has cracked down on high-rolling gamblers and their agents, once responsible for the majority of Macau’s casino revenue, forcing companies like Las Vegas Sands to pivot to mass-market customers.

From Barron's • Jan. 29, 2026

Ghislaine Maxwell compiled the birthday book, collecting sentiments from Epstein’s friends and then gifting the album to her high-rolling financier bestie.

From Los Angeles Times • Sep. 10, 2025

By the encore, he'd given up all pretence of being a high-rolling playboy.

From BBC • Mar. 30, 2025

It easily earned the No. 1 title but was not the high-rolling sendoff for one of modern cinema’s most iconic actor/character pairings that anyone hoped.

From Seattle Times • Jul. 2, 2023

The ear-splitting, chrome-encrusted Hog that Jann loaned me was a thrilling ride, and my high-rolling companions were friendly enough.

From "Into Thin Air" by Jon Krakauer