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1.
A free tournament in poker, where you can spend 3-4h grinding just to win 50 cent. Usually no lifers and retards play this since no skill is required.

Some people who are in deep financial misery play this in hope of grinding together some cash for a packet of cigarettes or some cheap liqueur.
After spending 10h of humiliating free rolling, Petter did not grind togheter enough cash for a packet of cigarettes so he had to smoke cigarette butts instead.

This is the hard life of a freeroller!
by Nisse G May 15, 2009
 
2.
A poker game or tournament with no entry fee, usually for a sponsored prize or satellite seat into a larger tournament.
"There's a freeroll at 3:00, you cheap bastard."
by Coell May 12, 2005
 
3.
A situation with no downside and a possible upside. Often used in poker to describe a free tournament in which real prizes can be won or a hand where players currently have the same rank hands, but one has a chance to improve and beat the other without reciprocal risk. Can also be used to describe any other life situation that conforms to the pattern.
"You playing freerolls again?" -"Yah, man. Guaranteed +EV."

"Jake and Derek were tied since they both had Ace-King, but because Jake had spades to match the two spades already out, he was freerollin' the flush."

"I threw my business card in the jar to try to win a catered lunch. I figured, 'Freeroll, why not??'"
by thecinimod October 03, 2007