Bastard of the Old Republic
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The task I set myself was to play the original Knights of the Old Republic, making the worst, cruellest, most spiteful, murderous and downright evil choices available at every choice. I've played the game before - in fact, it's one of my all-time favourites - but I was the most angelic creature in the galaxy. This wasn't going to be easy. This is the story of mysterious Republic Scoundrel, Simon Evil, and his adventures on the planet Taris.
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Of course, RPGs are always going to have you do things most would consider wrong. Finding a dead body on the ground, who thinks twice before rifling through their pockets to see if they had anything useful? Or an open cupboard in a public area, that no one complains when you open it? That's free stuff, right? But here the opportunities for wrongdoing made these acts feel perfectly mundane.
The first terrible thing I did hurt these poorest people the most. On the surface was a doctor's office. He was a kindly man, assisted by a rather unpleasant and slimy individual, and offered me free treatment. Talking to him like complete dirt, I made it clear that he'd better treat me for free, and then began poking around his office. Any locked door was an open invitation to Simon Evil, and I immediately busted it open, to the doctor's horror. He was secretly treating the very poorest citizens, for free, against the wishes of the crimelord Davik and the Sith occupiers. The conversation options presented me with wonderful choices, where I could help him in his endeavours, support this altruism and heap praise upon him. I told him that if he didn't give me all the money and health packs he had, I'd report him to the authorities. He handed it all over in a panic. But this wasn't the terrible thing I did.
It hurt to do it. Seriously, I physically winced. People who run illegal clinics in terrifying dictatorships around the world are some of Earth's greatest and bravest heroes. Blackmailing this wonderful man was a horrifying choice to make. But worse was my reaction upon learning that there was a serum that cured the disease that was killing the poor in their thousands. With a sample of this serum, currently controlled by the Sith, he would be able to synthesise enough to give it away and eradicate the disease completely. I had to find that serum, and I had to make sure it never got to that doctor.