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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

His videos also showed off the high-rolling lifestyle he claimed to lead in Romania.

From BBC • Sep. 8, 2024

Jurors got a glimpse at the high-rolling social life Trump enjoyed before becoming president, full of celebrity wattage and bold-faced names.

From Seattle Times • May 10, 2024

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