This trophy requires you to win a match while playing with five other players. Obviously, the easiest way to do this is to play as each of the players. Once the game starts, and at your earliest convenience, you should be able to simply make each player go bankrupt in turn.
While I have no reason to suspect this, the trophy may not pop if the last player simply opts to give up rather than landing on a property that sends them into bankruptcy. If this is the case, simply make sure that the last player goes out in such a manner.