Medium Humanoid (Imperial), Chaotic Evil

Armor Class 16 (padded armor)
Hit Points 71 (13d8 + 13)
Speed 30 ft.

13 (+1) 20 (+5) 12 (+1) 17 (+3) 15 (+2) 18 (+4)

Saving Throws Agi +8, Wil +5, Per +7
Skills Acrobatics +8, Deception +10, Performance +10, Stealth +8
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Senses passive Perception 12
Languages Tamrielic

Challenge 8 (3,900 XP)Proficiency Bonus +3
Carefully Clothed. Cicero ignores disadvantage on Stealth checks from wearing Light or Medium armor.

Fool of Hearts. If Cicero makes a successful Personality (Deception) or Personality (Performance) check against a creature’s contested Willpower (Insight) check, the next time he hits that creature with an attack roll within the next minute it is considered to be a critical hit.

Heroic Resistance (1/Day). If Cicero fails a saving throw, he can choose to succeed instead.

Mother’s Keeper. Cicero has advantage on attack rolls against any creature within 30 feet of the Night Mother or The Listener. If Cicero is within 30 feet of the Night Mother or The Listener, he gains a +1 bonus to AC and saving throws.

Sneak Attack (1/Turn). Cicero deals an extra 14 (4d6) damage when he 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 Cicero doesn't have disadvantage on the attack roll.
Multiattack. Cicero makes two dagger attacks, and then can use Mad Jester.

Dagger. Melee or Ranged Weapon Attack: +8 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7 (1d4 + 5) piercing damage.

Mad Jester. Cicero targets a creature within 30 ft. of him and performs an irritating antic. The creature must make a DC 16 Willpower saving throw. On a failed save, the creature has disadvantage on attack rolls against creatures other than Cicero for 1 minute. The target can repeat the saving throw at the end of each of its turns, ending the effect on a success. If the target fails the saving throw twice, it becomes frenzied for 1 minute, as Cicero becomes too irritating to bear. On a successful save, the target becomes immune to this effect for 24 hours.
Bonus Actions
Cunning Action. Cicero takes the Dash, Disengage, or Hide action.
Legendary Actions
Cicero can take 1 heroic action, choosing from the options below. Only one heroic action can be used at a time and only at the end of another creature's turn. Cicero regains spent heroic actions at the start of his turn

Madman's Jig. Cicero moves up to half of his speed without provoking opportunity attacks.

Laughing Killer. Cicero makes a dagger attack. On a hit, the dagger does an additional 5 (2d4) psychic damage.

Found In: Terrors of Tamriel


"The world has seen the last of Cicero, the man. Behold Cicero, Fool of Hearts—laughter incarnate!"
– Cicero

Keeper of the Night Mother during the 4th Era, Cicero is completely mad, a fact that becomes obvious to anyone who should speak to or interact with him. While he plays the part of the fool—quite literally wearing a jester’s outfit—Cicero should not be taken lightly. He is an expert assassin, master of infiltration, horribly deadly with a dagger, and is the last remaining survivor of the Dark Brotherhood’s presence in Cyrodiil.

Descent into Madness. Earlier in his life, Cicero was your average Dark Brotherhood assassin. After the death of the Listener, Cicero was chosen to be Keeper of the Night Mother. Before this, he was assigned to, kill a particular jester. The jester laughed endlessly, even as Cicero stabbed him to death. This bizarre response stuck with Cicero, and as the Cyrodiil chapter of the Dark Brotherhood’s numbers slowly fell, so too did Cicero’s sanity. At first, the silence from the Night Mother drove Cicero mad. Then it was the laughter—the jester’s laughter—screaming from the Void. Eventually the laughter stopped, and after the only other member of the Brotherhood disappeared, Cicero gave himself a new title: The Fool of Hearts.

Mother’s Loyal Servant. Cicero is heavily devoted to the Night Mother and his role as Keeper. He managed to smuggle her out of Cyrodiil and across Skyrim, caring for her and keeping her preserved every step of the way. Even in the face of silence from her, Cicero remains devoted. He finds Astrid’s disdain for tradition and the Five Tenets to be heretical, and hopes to change her and her “family’s” ways. He also hopes to locate a new Listener, something that may come about sooner than he thinks.