The Cheshire

Inspired by the mysterious Cheshire Cat of Wonderland, Rogues who follow this archetype specialise in deception, disappearance and psychological manipulation. Rather than relying purely on physical prowess, they torment their victims by slowly chipping away at their sanity. Their attacks leave behind supernatural marks that cause whispers, hallucinations and increasingly distorted perceptions of reality.

A Cheshire Rogue rarely fights fairly, preferring to vanish into thin air, reappear somewhere unexpected and toy with their enemies until they can no longer distinguish friend from foe. To face a Cheshire is not simply to fight an enemy, but to experience a descent into madness from which there may be no escape.

Now where has that cat gone?

As a bonus action, you can magically become invisible until the start of your next turn.

This invisibility ends early if you make an attack, cast a spell, or force another creature to make a saving throw.

You can use this feature a number of times equal to your proficiency bonus, and you regain all expended uses when you finish a long rest.

Playing With Your Food

You've become increasingly comfortable manipulating your victims, appearing and disappearing wherever you please.

Now You See Me: Immediately after using Cheshire's Disappearance, you can teleport up to 15 feet to an unoccupied space you can see.

A Cat's Game: When you hit a creature that already has at least one Madness Mark, you can apply an additional Madness Mark, even if you have already applied one that turn.

You can use A Cat's Game a number of times equal to your proficiency bonus, regaining all expended uses when you finish a long rest.

A Grin Without a Cat

You have mastered the art of driving your victims beyond the limits of their own perception.

Total Madness: As a bonus action, choose one creature within 60 feet that has three of your Madness Marks. The creature must make a Charisma saving throw against your Madness Save DC.

On a failure, the creature becomes incapacitated, and its movement speed becomes 0 until the end of its next turn. It perceives multiple hallucinations of you surrounding it.

On a success, the creature suffers no additional effects.

Regardless of the result, all Madness Marks on the target disappear.

Once you use Total Madness, you cannot use it again until you finish a long rest.

The Cheshire's Curse: When a creature with at least one Madness Mark dies within 30 feet of you, you can immediately use Cheshire's Disappearance without expending a use.

Wonderland's Distortion

Your victims no longer experience the world as it truly is. Their senses become unreliable and reality begins to twist around them.

Your Madness Marks gain the following additional effects:

The Whispers: The creature also has disadvantage on Wisdom (Investigation) checks.

The Distortion: The creature's movement speed is reduced by 10 feet.

The Madness: Whenever a creature fails its saving throw against your third Madness Mark, it also cannot take reactions until the end of its next turn.

Additionally, whenever a creature with three Madness Marks fails its saving throw against The Madness, you can use your reaction to teleport up to 15 feet to an unoccupied space you can see.

This teleportation does not provoke opportunity attacks.

Madness Marks

our attacks carry a supernatural curse that slowly corrupts the minds of your victims.

Whenever you hit a creature with a weapon attack, you can inflict one Madness Mark on it. You can only apply one mark per turn.

A creature can have a maximum of 3 Madness Marks. Marks last for 1 minute, and applying another mark refreshes the duration of all marks on that creature.

1 Mark – The Whispers: The creature begins hearing voices and distant laughter. It has disadvantage on Wisdom (Perception) checks.

2 Marks – The Distortion: The creature struggles to distinguish reality from illusion. It has disadvantage on its next attack roll on each of its turns and cannot make opportunity attacks.

3 Marks – The Madness: The creature must make a Wisdom saving throw against your Madness Save DC. On a failure, it becomes frightened of you until the end of its next turn. On a success, it resists the additional effect.

Your Madness Save DC equals 8 + your proficiency bonus + your Dexterity modifier.

A creature that succeeds on its saving throw is immune to the additional effect of your third Madness Mark for 24 hours, but can still accumulate marks.

All Madness Marks disappear after 1 minute or if you die or become incapacitated.