gangster roll

A person who sells products and had a roll of cash bundled in an elastic. Generally contains massive cash. Gangsters and mobsters favored way of carrying money.

I bought golf balls from this little girl and she pulled out a large gangster roll and put my cash in.

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that's how gangsters roll

The way gangsters act/behave and how they go about doing things in their everyday lives. Often said by people who are not gangsters when they do something they think is cool.

Person 1: "So that guy was talking shit to me ya know."

Person 2: "So what did you do about it?"

Person 1: "I busted a cap in his ass and then fucked his girlfriend!"

Person 2: "That's how gangsters roll!"

Person 1: Fuck yeah!"

Another example:

"I beat that video game without dying once. Now that's how gangster's roll."

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Gangster roll

beating the fuck out of someone

Let’s gangster roll their ass!