This start with my cousin as a DM accepting a Chaotic Neutral in his campaign. I was playing a halfling assassin named Azoth, and role it with a bipolar attitude, so i was fair most of the times, but a complete savage in others. The DM of course, tried to negate the bad things i did if i didn´t role high enough with negative or nearly death situations "Oh you try to burn a house and rolled 12? You alarm everyone inside and the guards try to find you". Other situation consisted in the rest of the party screwing the evil things Azoth did like not helping "Why i can´t find my weapons? Maybe the obvious thief has it" said everyone looking at me. After a few sessions, my character was hated by the survivors of a destroyed city, a Balrog in another dimension, a group of Ents, a Dragon and so on. Thanks sneak attack and stealths checks.
At a time, the DM wanted to see our party burn, so he allow the Deck of Many Things in the campaign. While in combat, i draw a card named "Ruin", so i was left only with my magic sword in hand against a group of mind flayers. Everything i stole dissapear, even my money and non magical equipment. With nothing left to do, i draw another named "Knight" and a halfling fighter named Jerico appear to serve and aid me. After the battle, my party was laughing at my disgrace, but i simply asked for coins to buy another equipment. Sessions passed and i was poor with nothing that i could steal. I think it was a plan of the DM to stay away from populated places for a while to screw me.
The first town we come near, was on fire, with few survivors left after an undead dragon attack. The party knew that a pack of zombies would arrive in a few hours to finish the job, but i tried to look for anything to rob. The party didn´t let me but were distracted with how to take all the survivors to a city two hours away. Me, my guard Jerico and another from my party stayed voluntarely (Me with intentions of robbing anything obviously). We decided to hide in the Mayor house with the few survivors that couldn´t make the trip away. I investigate the town, but it only had eight burned houses and two ruined barns (I dont remember why, but i took a note of that). We couldn´t prepare enough, so we used a bottleneck in a big office inside the Mayor house to keep the undead in check until the rest of the team came back. The battle left the Mayor house in ruins and the rest of the town in ashes.
I ask my cousin if i can make a perception throw to see if i could find anything worth taking. He told me there was a small safe between the ruins, so i lockpick it in an instant. It had a royal paper giving the title of mayor with the name of the one governing the town and 10 gold coins. I was going to throw it away in anger when i realize something. I kept everything in my bag pack and followed the crew towards the city. The session was about to end, so i ask the DM if i could do a little trip alone towards to where the king or queen was. He didn´t get the idea of what were my intentions, but i convince him, as i was one of the saviours of the survivors of the town.
I get a meeting with the King, so i speak the following "I bow to you my liege with bad news. The town i lived in was attack and the mayor of that town is dead. Before he passed away, he left me the title to me so i could save the villagers. I have in hand his title and have intentions of rebuilding the town to its former glory so we could serve you my liege. I only ask for some investment so i can start constructions" the party and the DM looked at me and were left speechless. The party tried to stop me, but I remark that i was alone, so they couldn´t say or know anything. I told the DM out of character, that there where eight houses plus the Mayor one and two barns the town. The DM was very surprised, and knew that there was almost no reason to ask me for a charisma saving throw. He rewarded me with 10k of platinum coin and a lot of laughter for that.
I knew the DM would later role something bad against me with intentions of making me lose the money, so i gave 8k to the survivors to gain a little of good karma. I was more rich than ever, the members of the party thought my character was now a good guy (although everyone hated him to the guts). And so the adventures of Azoth goes on, finding new ways to trick the party or the DM