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High Roller 

A “High Roller” is someone who spends lots of money carelessly, blowing money fast and recklessly. The term originated from high stakes players who place large bets at the casino.
High Roller by YungMon August 23, 2016

high roller 

When a person is a "hi roller" they mean they are in the high life. Have lots of money. Meaning they are very rich
High roller. Yeah you know I'm a high roller

High roller 

A schoolgirl who shortens a uniform skirt above the knee (or higher) by rolling the waistband. Typically done for comfort or fashion purposes. Rarely to be provocative.
High rollers are in the frontline of society's war on young women's bodies.
High roller by Tabasco Jones March 13, 2022

HR9 high rollers 

A rebilous gang from N. Carolina although a new chapter was found in north west washington. The gang is mostly known for their drug dealing, that is where the name high roller came from, They often wear the colors green and blue. the color green represents money from the crimes, It is unknown why they wear blue. They are currently rivals with most juggalos and nortenos although they are EBK.
#1 oh shit its the HR9 high rollers
#2 we better leave them alone
#1 Good idea.

High Roller 

Rich guy that has a nice car, nice clothes and buys everything he likes.
Yo that guy with that benz a high roller yeah.
High Roller by Dazzle August 5, 2003

high roller 

One of a group of 4 individuals that are highly skilled in poker and hustle people at the poker table. They always dress nicely at the poker table and have good table etiquette. A high roller is often feared by other poker opponents.
Bob: "I heard the high rollers were playing in this tournament."
Jake: "Yeah, they are the people with ties and triple everyone elses' chipstack."
Bob: "It's ok, we can always play for 5th place."
high roller by The High Roller$ September 7, 2008