Warlock Patron: The Cheshire Cat

The Cheshire Cat is a being of enigmatic chaos, an Archfey who exists outside the bounds of reason and order. As your patron, it is an ever-present grin in the shadows, a whisper in the wind that guides you—sometimes toward safety, sometimes toward folly. It is a creature of contradictions, offering wisdom cloaked in riddles and assistance tainted with mischief. The Cheshire Cat thrives on unpredictability, reveling in the chaos it sows, and it expects its warlocks to embrace the same.

Physically, the Cheshire Cat manifests as a spectral feline with shimmering, ever-shifting fur, marked by swirling patterns of impossible colors. Its hypnotic eyes glint with unsettling knowledge, and its infamous grin lingers long after its body fades into nothingness. To swear fealty to the Cheshire Cat is to surrender to the absurd, the unpredictable, and the delightfully maddening.

The Cat’s gifts often come at the cost of clarity. It delights in warlocks who play along with its games and spread its chaotic influence, whether that means sowing disorder or simply reminding the world of the folly of control. Its guidance is sporadic and its motives unclear, but one thing is certain: with the Cheshire Cat as your patron, no path is ever straightforward.

Expanded Spell List

The Cheshire Cat lets you choose from an expanded list of spells when you learn a warlock spell. The following spells are added to the warlock spell list for you.

Expanded Spells

Spell Level	Spells
1st	Color Spray, Tasha's Hideous Laughter
2nd	See Invisibility, Phantasmal Force
3rd	Blink, Catnap
4th	Compulsion, Confusion
5th	Telekinesis, Modify Memory

Chaos of the Cheshire Cat

Starting when you choose this patron at 1st level, your patron’s magic is overwhelming with chaos as it flows through you. Anytime after you cast a spell of 1st level or higher, roll a d20. If you roll a 1-2, roll on the Chaos magic table to create a magical effect. If that effect is a spell and it normally requires concentration, it doesn't require concentration in this case; the spell lasts for its full duration.  Any spell effect does not cost a spell slot unless specifically stated. 

d100 Range	Effect
01–04	Cheshire’s Illusions: You cast minor illusion at will for the next minute. The illusions resemble Cheshire Cat-like grins and eyes.
05–08	Furry Fiasco: Your body suddenly sprouts and is covered in soft, colorful fur resembling that of a Cheshire Cat. As you move, the fur harmlessly sheds in faint, glowing tufts that disappear after a few seconds. This effect can be ended with a remove curse spell.
09–12	Chaotic Damage: You are overwhelmed by chaotic energy and take 2d10 psychic damage.
13–16	Mirror Mischief: You cast mirror image on yourself; each duplicate sports a Cheshire grin that distracts foes, granting you advantage on your next attack roll.
17–20	Drink Me/ Eat Me: Roll a d10. Your height changes by a number of inches equal to the roll. If the roll is odd, you shrink; if it's even, you grow.
21–24	Potent Surge: Your spells surge with extra potency—maximize the damage of the next damaging spell you cast within the next minute.
25–28	Up is down and Down is Up: You cast confusion centered on yourself. You roll your saving throw at disadvantage
29–32	Butterfly illusion: Illusory harmless butterflies and flower petals flutter in the air within 10 feet of you for the next minute.
33–36	Vital Restoration: You regain hit points equal to 2d10 plus your Charisma modifier.
37–40	Cat Scratch Fever: You and all creatures within 30 feet of you gain vulnerability to piercing damage for the next minute. As your skin becomes similar to that of a cats scratching post. The effects fade after 1 minute, and skin turns back to normal.
41–44	Tea Time: You turn into a teapot until the start of your next turn. While a teapot, you are incapacitated and have vulnerability to all damage. If you drop to 0 hit points, your teapot breaks, and your form reverts.
45–48	Swift Transposition: You teleport up to 60 feet to a random location, leaving behind a faint, distracting grin.
49–52	Cat got your tongue: You can not speak for the next minute.
53–56	Over groomed: All of your hair falls out but grows back within 24 hours.
57–60	Dream state: You start to glow faintly with shifting purple and pink hues for 1 minute. While glowing, attack rolls against you have disadvantage. A creature is unaffected if it can't see or, if it relies on senses other than sight, such as blind sight or tremor sense.
61–64	Cheshire’s Invisibility: Each creature within 30 feet of you (excluding you) becomes invisible for the next minute. The invisibility ends on a creature when it attacks or casts a spell.
65–68	Whimsical Melody: For the next minute, a faint, whimsical melody follows you, audible only to you.
69–72	Charming Presence: You gain advantage on all Charisma-based skill checks for the next 10 minutes as your enigmatic charm influences those around you.
73–76	Mental Muddle: Your mind is scrambled; you suffer disadvantage on attack rolls and ability checks for 1 minute.
77–80	Are you seeing what I’m seeing: A unicorn controlled by the DM appears in a space within 30 feet of you, then disappears 1 min later. Only you can see the unicorn.
81–84	Echoing Laughter: A burst of chaotic laughter erupts from you. Each creature within 30 ft. must succeed on a Wisdom saving throw or become frightened of you until the end of their next turn. Creatures that can't be charmed are immune to this effect.
85–88	Frozen in Chaos: You are momentarily paralyzed by overwhelming chaos, unable to move until the end of your next turn.
89–92	Just a floating head: You are affected by the levitate spell, and your body becomes invisible, leaving only your head visible. This effect lasts for 1 minute.
93–96	Cheshire’s Ire: A wave of chaotic energy erupts, forcing you to lose a spell slot as if a spell has been cast.
97-100	Cheshire’s grace: You regain all expended spell slots

Delightfully Maddening

Starting at 3rd level, the Cheshire Cat’s mischievous influence infuses your magic with a maddening energy. Once per turn, when you deal damage to a creature with a spell, you can cause the spell to deal additional psychic damage equal to your Charisma modifier (minimum of 1).Additionally, the target must succeed on a Wisdom saving throw against your spell save DC or have disadvantage on its next attack roll.

You can use this feature a number of times equal to your Charisma modifier, and you regain all expended uses after a short rest.

Smile in the Shadows

Starting at 6th level,You have learned a few tricks from you patron including the old, disappearing act. You can become invisible as a bonus action for 1 minute. While invisible, you can still be heard laughing or speaking if you chose it, and your grin may appear momentarily when you speak if you choose as well. This invisible condition ends if you attack or cast a spell. The use of this skill increases to twice at 10th level, and three times at 14th level. 

Once you use this feature, you can’t use it again until you finish a short rest.

Wonderlands Whimsy

Beginning at 10th level, you have learned to embrace the ways of Wonderland.Up is in fact Down, and Down is Up! You gain resistance to psychic damage and advantage on saving throws against being charmed or frightened. Additionally, when you fail an Intelligence, Wisdom, or Charisma saving throw, you can roll again and take the second result.

Cheshire's Reality

Starting at 14th level, you have fully embraced the madness of Wonderland and realize we're all a little mad down here. Once per long rest, as an action, you can cast [Tooltip Not Found] without expending a spell slot, transforming the landscape into a surreal, dreamlike environment. At 20th level, your use increases to twice per long rest.

You must finish a long rest before you can use this feature again.