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So many evil things to speak of. On my first play through I had a King named Osmond of England who kept having daughters, think he was up to six daughters and three seperate wives at the age of fifty. Kept having to assassinate the wives as they would get too old so I could marry someone else and try for a son. If I remember right it was probably the fifth wife that finally gave me a son. Did the Henry VIII thing in a way only I succeded :)

Although in my latest play through as the Weimars, I think the most evil thing I did was cause what could play out to be the downfall of the HRE. My wife the Duchess of Bavaria plotted to depose the current Kaiser, and didn't invite me into the fun so I assassinated him, then his successor. Then the third Kaiser took the throne, and all hell literally broke loose probably close to 3/4s of the empire has either declared independence or aligned themselves in a war in favor of another Kaiser. I gained my independence though through these means as the Duke of Saxony. So even though I have that family stuff for the holiday weekend I'm having a hard time pulling myself away from the mischief I've caused in game.
 
I play this game in... remarkably nice fashion, it seems.

My only "evil" ruler was Queen Marija "The Dragon" of Croatia, and frankly, those idiots should have noticed that she had Wroth, Cruel, and Impaler before they decided to rebel when she took the throne -- not her fault she was one of five sisters and no sons.
 
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The Popes Spymaster

When I played the count of Orvietto (House Orsini) in 14th Century game, I became spymaster for the Pope.

Ah hah! But it turns out that it is a Frankish Pope (we are in Schism, naturally).

I am his spymaster! There is 0% chance that I can be caught killing the little Frankish monster...
 
My wife is the sister and heir to the king of England. To ensure that she remains the heir I am killing the kings children - 6 children in total to date. They are also my nieces and nephews bwahahahaha
 
One time, when I was playing as the King of Poland, a count rebelled against me. Naturally, I quickly overpowered the county and the Count was killed in battle. He left his lands and the rebellion in the hands of his three year old son, whom I promptly made my prisoner. I needed an example to teach others not to revolt, so I executed the three year old.
 
-Assassinated 6 under-aged Capets. Just because I wanted to lessen the Capet influence in recently conquered France. (and the chances were 70% success, 10% discovery - I just had to try that!)

-Assassinated the Emperor of Both Roman Empires, his four sons (leading to a split of the Empires), then assassinated the Empress of the Byzantine Empire in order to brake the alliance between the Beasts. Then assassinated the Pope who hated me and it would be just a matter of time before he would have me excommunicated. As my ruler Angus the Accursed was turning 80, I assassinated two heirs to my throne in order to secure a good ruler.

At the Grand Tournament celebrating his 80th birthday, Angus then turned homosexual (though his wife got pregnant the other day), civil war started and three months later Angus the Accursed died as a homosexual craven slothful kinslayer with -350 Piety. Karma forever.

E: Thinking about it, Angus was actually not the nicest guy in town.
 
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Most evil thing I've done?

Betrothed me and my son to two twin French princesses in my court who were aged 5 (my character was 42 and my son was 21)

Then when they both came of age I impregnated princess number 1 (my wife) and also had an affair with princess number 2 (my sons wife)

Both these unions produced sons, I then assassinated my original son to ensure that my new son would have claims on the kingdom of France

To top of it off and named my new baby son after the son I just assassinated.
 
I developed moral objections to marriage policies aimed at taking away a duchy or a couple of duchies from a different king. As in, picking the bride with this specific goal in mind and taking all sorts of precaution. Legal and perhaps normal and ethically neutral if done for reasons like alliance, love, stats even. But it struck me as objectionable if used in a conscious land grabbing scheme.

Betrothals of very young people or marriages of very close relatives also happened in my game but I don't regard that as evil. More worried about stuff like a 16 year old princess being sent off to marry a 70 year old king older than her father. This did feel bad.
 
Killing or had my wife killed. Thoroughly murdered an entire family just for the lulz. Got several of my distant relatives and heirs by seniority laws "strangulated by silk ropes". Assassinated low diplomacy popes (which circle of hell do you go to after this...).
 
OMG so much evil here.

I thought marrying my old aunt 45+ to the Scottish heir in matrilineal marriage was evil. They must've been desperate for an alliance and she was a Princess after all.
 
I killed my son because he was a homosexual.

Well, it was the Year of Our Lord 1102. I thought it would be acceptable.

Faced with the same situation, I married the son to a Lustful Hedonist.

I didn't ask about the details, but she got a couple of kids out of him.
 
Nothing too fancy here. I just had a Queen murder her infant son. Sure, I could assume that she had an assassin do it, but she seemed awfully familiar with the details. Besides, how hard could it be to make a baby choke on its own blood? This is just after I joined a Crusade for the sole purpose of earning enough piety to get the Pope to grant a divorce. Then I sent 2000 men to die in the desert just to keep up the charade.

Apparently God didn't like this one bit, because my Queen wasn't able to produce an heir with her new lustful hubby in their happy, matrilineal marriage. Then she died of Typhoid.
 
No matter what yardstick you use I have created an evil dynasty.

Murdered wives and children, some still in the cradle. Wiped out sons, grandsons, and great grandsons. Fathered bastards upon sons and murdered them, I may even have married the widow but more likely I married her off to some third rate untitled courtier.

I have murdered the wives of other rulers to end alliances that could be called against me, broken truces, banished vassals, and caused vassals to revolt.

I have murdered bishops and popes as well as my own wards. I have even killed my own counsel members.

Nothing is off limits or out of bounds when it comes to smooth rule.

Of course there were many I couldn’t manage to kill, mores the shame.

What is more, I felt justified in doing it and had no remorse.
 
After a woman murdered one of my vassels I throw her in prison where she promptly gives birth before I execute her. 30 years later the babe is still alive and still in my prison when she's finally mastered enough of the human language to ask for leniency and house arrest before being escorted to the oubliette.
 
In one of my games when my ruler died, I took over as the son.

Few months later I realized my character had an affair after the bastard was born. Problem was the person my character had an affair with was my daughter-in-law. This made my son really angry since his own father cuckolded him. I killed(jailed and executed) the girl and the bastard child to appease my true born son as I wanted him to be my heir.

Resulted in quite a few rebellions. And the son was angry I killed his wife.
 
My cruel, impaler, zealous, king of wroth had his heir fall from a tall tower just because he was ginger... I saved him from a life of sicilian sunburn...