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Cicero

Cicero is an Imperial assassin and Keeper of the Dark Brotherhood. As Keeper, he is responsible for caring for the Night Mother's body and casket. Having spent several years as the sole member of the Dark Brotherhood in Cyrodiil, Cicero fled to Skyrim with the Night Mother's body, where one last chapter of the organization remained active as of 4E 201. He hoped to find a haven for the Night Mother, and to find a Listener who could rejuvenate the Brotherhood. These he found in Skyrim and was heavily involved in the assent of the new Listener of the Dark Brotherhood, along with the assassination of Emperor Titus Mede II and is personally responsible for the assassination of Gaius Maro; the son of Commander Maro in Dragon Bridge.   He is currently travelling Skyrim undercover in Cassian's Travelling Circus, under the monkier Cicero the Fool. Where he works as a performing jester.   Quotes:
"He he he... Crazy? Cicero? He he he he... That's madness..."
"Our sweet Lady is maiden, mother... and crone..."
"...ho ho ho, and hee hee hee, break that lute across my knee... and if the bard, should choose to fight, why then I'll set his clothes alight..."
"...and if I spy a singing bird, I'll snap its neck before it's heard..."
"...and I said to the baker, "You're not dead! You're a faker!" But if that's your wish, I'll oblige..."
"...oh if I chance to see a cat, I'll feed its corpse to my pet rat..."
"...and he says to the man, "That's not a horker! That's my wife!" Ha ha ha ha ha... Ah... I love that one..."
"...when I next meet, that fair maid Nelly, I'll plunge my knife into her belly..."
"...tra la la, tra la lee, da da dum dum, dee dee..."
"...madness is merry, and merriment's might, when the jester comes calling with his knife in the night..."
"...What? Mother? Is that your voice I hear? Hmm... No, no... Just my head playing tricks... Foolish Cicero..."
"...need to sharpen my blade... make it shiny, gleamy, and oh so deadly..."
"...dear Cicero will keep you from harm, sweet Mother. Forever and always..."
"...is there singing in the Void? Dancing...? Surely the Dread Lord will at least allow poor Cicero to caper..."
"...Cicero is hungry... ...need a sweetroll... or a carrot..."
"...need to get Mother some flowers... pretty, pretty flowers..."
"...must oil Mother soon... ...get all the hard to reach places..."
Cicero wears a unique Jester's Outfit with a jester's hat and gloves. He wields and iron dagger in battle and carries two Potion of Plentiful Healing. He also carries an assortment of rare loot and gold.
Children

Cicero

Medium Imperial, Assassin, Chaotic Evil

Armor Class 17 (Mage Armour) (+4 melee)
Hit Points 58 (9d8+18) 9d8+18
Speed: 30 ft

STR

9
( -1 )

DEX

18
( +4 )

CON

14
( +2 )

INT

12
( +1 )

WIS

15
( +2 )

CHA

13
( +1 )

Saving Throws Dexterity +8, Intelligence +5, Charisma +5
Skills Acrobatics +12, Perception +6, Performance +5, Sleight of Hand +8, Stealth +12
200px-LG-cardart-Cicero_the_Betrayer.png
Senses passive Perception 16
Languages Common, Shadowmarks, Daedric
Challenge Rating 5
Proficiency Bonus +4

Cicero is a 9th-level spellcaster (Arcane Trickster), thier spellcasting abilty is Intelligence (spell save DC 13, +5 to hit with spell attacks) they have the following Wizard spells prepared:  

Cantrips

Mage Hand, Minor Illusion, True Strike  

1st-level Spells (3/4 slots)

Hideous Laughter, Mage Armour, Puppet, Silvery Barbs  

2nd-level Spells (2 slots)

Mischief, Shadow Blade

1/day:


The Gift

Dissonant Whispers, Misty Step  

Cloak of Shadows

When in dim light or darkness, Cicero can use his action to become invisible. He remains invisible until he makes an attack, casts a spell, or is in an area of bright light.  


Special Abilities

Sneak Attack. Once per turn, Cicero deals an extra 5d6 damage when it hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Cicero that isn’t incapacitated and the rogue doesn’t have disadvantage on the attack roll.   Cunning Action. Cicero can take a bonus action on each of his turns in combat. This action can be used only to take the Dash, Disengage, or Hide action.   Mage Hand Legerdemain. Cicero's mage hand is invisible and can be controlled using a bonus action.   Uncanny Dodge. When an attacker Cicero can see hits him with an attack. That attack's damage is halved.   Evasion. When Cicero is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeed on the saving throw, and only half damage if he fails.   Magical Ambush. If Cicero is hidden from a creature when he casts a spell on it, the creature has disadvantage on any saving throw it makes against the spell that turn.   Defensive Duelist. +4 to AC against melee attacks.   Jester's Outfit. On a critical hit with a light and finesse weapon. The attack always applies sneak attack damage.

Actions

Off-Hand Attack. Cicero can make an (unmodified damage) attack with thier off-hand, as with two-weapon fighting.   Iron Dagger. Melee Weapon Attack. +8 to hit, reach 5ft, one target. Hit: (1d4+4) piercing damage.   Shadow Blade. Melee or Ranged Weapon Attack: +8 to hit, reach 5 ft. or range 20/60 ft,, one target. Hit: (2d8) psychic damage.


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