Top Definition
Trollopoly is a term that is associated with the act of trolling. If you do not know what trolling means, I encourage (not really) you to search for the term on this site so you get a better understanding on what this is all about. Anyway, the act of trolling shares many similarities with monopoly which allows for these two things to be juxtaposed.

Firstly, people who decide to troll can end up in jail....under serious circumstances. If you are extremely unlucky and decide to troll someone of 'high status' on twitter, facebook etc., you might get fucked with a civil lawsuit which may involve a defamation case. For those who are poor, jail may result. This aspect is clearly evident in the monopoly game with the 'go to jail' area which causes a player to go to jail if they roll a shit number.

....To be continued...
Dude 1 - Don't you think trolling is like the monopoly board game?
Dude 2 - Why yes, let us call it 'trollopoly'
by JennyWong May 30, 2012

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