Carry the ruby until it posesses you
On 2F, the top right door has a bureau with a ruby in it. Pick up the ruby. It will now slowly kill you (it takes about 50-60 moves to happen). You will see the Game Over skull three times and still be able to proceed – the fourth time it will kill you and unlock this trophy.
You can drop the ruby in the back yard (accessed via the game room on 1F) if you don't want to just spam random actions 50-60 times to unlock this trophy.