Should I Kill Cicero or Spare Him?

When It Makes Sense

• Good fit: Sparing Cicero is reasonable if you are playing a stealth-focused Dragonborn and want a specialized assassin follower. After the Dark Brotherhood questline concludes, a spared Cicero becomes available as a follower with strong Sneak, One-Handed, and Archery skills. He also retains his Jester’s Clothes, which provide bonuses to sneak, one-handed damage, and archery, making him a thematically appropriate and mechanically useful companion for players who rely on silent movement, backstabs, and ranged ambushes. Keeping him alive also preserves his role as the Keeper of the Night Mother, which adds to the atmosphere and internal logic of the Sanctuary.
• Good fit: Killing Cicero makes sense if you are roleplaying a ruthless, profit-driven assassin or if you simply do not want him as a companion. The contract offers a 500 gold reward, and his body can be looted for the Jester’s Clothes set and the Blade of Woe dagger. Players who prefer not to manage another follower, find his voice lines and laugh repetitive, or want to complete the contract exactly as Astrid intended may find killing him the cleaner and more profitable option. It is also a fitting choice for a Dragonborn who views mercy as weakness within the Dark Brotherhood.

When You Should Avoid It

• Warning sign: Avoid killing Cicero if you are a completionist or you value unique followers. Once he is dead, he cannot be recruited later, and you lose access to his post-quest commentary, Keeper roleplay, and the dynamic he adds to the rebuilt Sanctuary. The 500 gold reward is modest compared with the long-term utility of a stealth-focused companion, especially if your character uses light armor and sneak attacks. If you enjoy collecting every possible follower and experiencing all companion dialogue, killing him removes content permanently for that playthrough.
• Warning sign: Avoid sparing Cicero if your roleplay demands strict loyalty to Astrid or the original Sanctuary hierarchy, or if you are trying to maximize immediate quest rewards. Sparing him skips the 500 gold payment and means tolerating an unstable character inside the Dark Brotherhood, which may feel inconsistent for a Dragonborn who eliminates threats without hesitation. It can also feel narratively strange if you have been playing as a cold, detached assassin up to that point.

Pros and Cons

Pros of Killing Cicero

• You receive an immediate 500 gold reward for completing the contract, which is useful in the early-to-mid game when resources are tight and training or equipment purchases matter.
• You can loot his Jester’s Clothes, Jester’s Hat, Jester’s Gloves, Jester’s Boots, and the Blade of Woe directly from his body, giving you guaranteed access to the outfit and weapon without needing to manage him as a follower or rely on pickpocketing.

Cons of Killing Cicero

• You permanently lose a unique, highly specialized stealth follower who can support assassin playstyles with strong Sneak and One-Handed abilities, as well as entertaining and lore-relevant dialogue.
• You miss his post-quest restoration of the Night Mother’s shrine, his Keeper roleplay, and the additional atmosphere and dark humor he brings to the rebuilt Dark Brotherhood Sanctuary.

Decision Checklist

• Do I want a stealth-oriented follower for the rest of the playthrough, or do I already have a companion I prefer?
• Is my character roleplayed as merciful, pragmatic, or ruthlessly loyal to the contract and Astrid’s orders?
• Am I more interested in the immediate 500 gold and guaranteed gear, or in long-term companion utility and roleplay flavor?
• Have I checked whether I can obtain the Jester’s Clothes and Blade of Woe another way, such as through pickpocketing or follower trading if I spare him?
• Would I regret losing access to Cicero’s dialogue and follower mechanics later in the playthrough?

Alternatives to Consider

The main alternative to killing Cicero is sparing him and recruiting him as a follower after the Dark Brotherhood questline ends. If you want his gear but do not want him as a permanent companion, you can spare him, temporarily recruit him, take his equipment through the follower inventory menu, and then dismiss him back to the Sanctuary. Another option is to kill him and use the 500 gold to hire a different mercenary follower, though standard hirelings do not match Cicero’s stealth specialization or unique personality. Some players also choose to save the game just before the decision and experience both outcomes across different characters or reloads. Finally, you can simply make the choice based on your preferred roleplay outcome and accept that Skyrim allows multiple valid playthroughs, so a different decision can always be explored in a future game.

Final Recommendation

For most stealth and assassin builds, sparing Cicero is the stronger long-term choice because he offers a unique, thematically appropriate follower with gear and skills that complement the Dark Brotherhood playstyle. For players who prioritize immediate rewards, prefer a loner playthrough, or are roleplaying a Dragonborn who follows contracts without mercy, killing him is a valid and mechanically rewarding option. Neither choice locks you out of the main questline, so decide based on your build and roleplay rather than fear of missing essential content. If you are unsure, consider saving before the decision so you can experience both outcomes without committing to one permanently. Since this is a video-game choice with no real-world consequences, either path is fine, but if you are concerned about permanence, saving beforehand is the safest approach.