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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.

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The Spanish island wants to shed its reputation as a hot spot for British bachelor parties and thrifty package holidayers and transform into a luxury destination for high-rolling tourists like Americans.

From The Wall Street Journal Sep. 13, 2026

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

“No family anymore and no money: that was how I started, and it’s no different now. But it’s not a way up, even with high-rolling guys. You should know that.”

From "Genuine Fraud" by E. Lockhart

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