Cheshire the Mad, Archfey of the Court of Madness

Shapechanger. Cheshire can change his appearance and his voice. He determines the specifics of the changes, including his coloration, hair length, and sex. He can also adjust his height and weight and can change his size between Medium and Small. He can make himself appear as a member of another race, though none of his game statistics change. He can’t duplicate the appearance of an individual he has never seen, and he must adopt a form that has the same basic arrangement of limbs that he has. His clothing and equipment aren’t changed by this trait. He stays in the new form until he uses an action to revert to his true form or until he dies.

Chaotic Flux. Cheshire's weapons are in a constant state of flux. Before each of his weapon attacks, roll a d3. If you roll a 1, the attack deals slashing damage. If you roll a 2, it deals piercing damage. If you roll a 3, it deals bludgeoning damage.

Aura of Madness. Cheshire's mere presence is enough to drive most creatures mad. He radiates a 10-foot radius sphere of maddening energy. Any creature that is within that area or that enters that area must make a DC 16 Charisma saving throw. On a success, they are not maddened and are immune to this effect for the next 24 hours. If they fail, at the start of each of their turns, they must roll a d6 and can only do what the result tells them.

     d6     Effect

     1       The affected creature does nothing on its turn and can't take reactions.

     2       The affected creature is forced to attack the nearest creature to it that is not Cheshire to the best of its ability.

     3       The affected creature moves in a random direction as decided by the DM.

     4       The affected creature attacks itself once and does nothing else on its turn.

     5       The affected creature spends its entire turn attacking a hallucinated creature that only it can see.

     6       The affected creature uses its entire turn to run as far away from Cheshire as it can.

A creature can repeat this saving throw at the end of each of its turns. On a success, the effect ends and the creature is immune to this ability for the next 24 hours.

Spellcasting. Cheshire is a 5th-level spellcaster. His spellcasting ability is Charisma (spell save DC 16, +8 to hit with spell attacks). Cheshire has following Bard spells prepared:
Cantrips (at will): Friends, Prestidigitation, Vicious Mockery
1st level (4 slots): Comprehend Languages, Silvery Barbs, Tasha's Hideous Laughter      2nd level (3 slots): Blindness/Deafness, Calm Emotions, Heat Metal, Silence                  3rd level (2 slots): Antagonize

1/day each: Fly, Invisibility, Levitate, Protection from Evil and Good, Stone Shape, Wall of Fire, Wind Wall

1/long rest: Identify

Jack of All Trades. Add +2 to any ability check Cheshire makes.

Dueling. When Cheshire is wielding a melee weapon in one hand and no other weapons, he gains a +2 bonus to damage rolls with that weapon.

Blade Flourish. Whenever Cheshire takes the Attack action on his turn, his walking speed increases by 10 feet until the end of the turn, and if a weapon attack that he makes as part of this action hits a creature, he can use one of the following Blade Flourish options of his choice. He can use only one Blade Flourish option per turn. Cheshire has 4d8 Blade Flourish dice that recharge on a short or long rest.

     Defensive Flourish. You can expend one Blade Flourish die to cause Cheshire's weapon to deal extra damage to the target he hits. The damage equals the number you roll on the Blade Flourish die. You also add the number rolled to his AC until the start of his next turn.

     Slashing Flourish. You can expend one Blade Flourish die to cause Cheshire's weapon to deal extra damage to the target he hits and to any other creature of your choice that he can see within 5 feet of him. The damage equals the number you roll on the Blade Flourish die.

     Mobile Flourish. You can expend one Blade Flourish die to cause Cheshire's weapon to deal extra damage to the target he hits. The damage equals the number you roll on the Blade Flourish die. He can also push the target up to 5 feet away from him, plus a number of feet equal to the number you roll on that die. He can then immediately use his reaction to move up to his walking speed to an unoccupied space within 5 feet of the target.

Action Surge. Cheshire can push himself beyond his normal limits for a moment. On his turn, he can take one additional action. Once he uses this feature, he must finish a short or long rest before he can use it again.

Combat Superiority. Cheshire knows maneuvers that are fueled by superiority dice.

     Superiority Dice. Cheshire has five superiority dice, which are d8s. A superiority die is expended when you use it. He regains all of his expended superiority dice when he finishes a short or long rest.

     Maneuvers. 

          Bait and Switch. When Cheshire is within 5 feet of a creature on his turn, he can expend one superiority die and switch places with that creature, provided he spends at least 5 feet of movement and the creature is willing and isn’t incapacitated. This movement doesn’t provoke opportunity attacks. You roll the superiority die. Until the start of his next turn, he or the other creature (your choice) gains a bonus to AC equal to the number rolled.

          Disarming Attack. When Cheshire hits a creature with a weapon attack, he can expend one superiority die to attempt to disarm the target, forcing it to drop one item of his choice that it’s holding. You roll the superiority die and add the result to the attack’s damage roll, and the target must make a DC 17 Strength saving throw. On a failed save, it drops the object he chooses. The object lands at its feet.

          Trip Attack. When Cheshire hits a creature with a weapon attack, he can expend one superiority die to attempt to knock the target down. You roll the superiority die and add the result to the attack’s damage roll, and if the target is Large or smaller, it must make a DC 17 Strength saving throw. On a failed save, he knocks the target prone.

          Quick Toss. As a bonus action, Cheshire can expend one superiority die and make a ranged attack with a weapon that has the thrown property. He can draw the weapon as part of making this attack. If he hits, roll the superiority die and add the result to the weapon’s damage roll.

          Commanding Presence. When Cheshire makes a Charisma (Intimidation), a Charisma (Performance), or a Charisma (Persuasion) check, he can expend one superiority die and add the number rolled to the ability check.

          Evasive Footwork. When Cheshire moves, he can expend one superiority die, rolling the die and adding the number rolled to his AC until he stops moving.

Mystic Conflux. Cheshire possesses an intuitive understanding of the way magic ebbs and flows within enchanted items. Such items attune easily to him, and he is able to sound out their secrets. He gains the abilities to attune up to four magic items at once and he can cast Identify without material components once per long rest.

 Know Your Enemy. If Cheshire spends at least 1 minute observing or interacting with another creature outside combat, he can learn certain information about its capabilities compared to his own. The DM tells you if the creature is his equal, superior, or inferior in regard to two of the following characteristics of your choice:

• Strength score
• Dexterity score
• Constitution score
• Armor Class
• Current hit points
• Total class levels (if any)
• Fighter class levels (if any)

Cruel. The challenges and struggles Cheshire has faced throughout his life have led him to delight in inflicting pain and anguish upon others. He gains four cruelty dice. His cruelty dice are d6s. You can roll only one cruelty die per turn, and a cruelty die is spent when you roll it.

You can roll a cruelty die under any of the following circumstances, with the indicated result:

• When he deals damage to a creature, spend one cruelty die to deal extra damage to the creature equal to the roll.
• When he scores a critical hit, spend one cruelty die to gain temporary hit points equal to the roll.
• When he makes a Charisma (Intimidation) check, spend one cruelty die and add the roll to his check.

He regains all spent cruelty dice when he finishes a long rest.

Chaotic Movement. When Cheshire uses the Dash action, difficult terrain doesn't cost him extra movement on that turn. When he makes a melee attack against a creature, he doesn't provoke opportunity attacks from that creature for the rest of the turn, whether he hit or not.

Shapechange. As an action, Cheshire can change his appearance and his voice. He can determine the specifics of the changes, including his coloration, hair length, and sex. He can also adjust his height and weight and can change his size between Medium and Small. He can make himself appear as a member of another race, though none of his game statistics change. He can’t duplicate the appearance of an individual he has never seen, and he must adopt a form that has the same basic arrangement of limbs that he have. His clothing and equipment aren’t changed by this trait. He stays in the new form until he uses an action to revert to his true form or until he dies.

Multiattack. Cheshire makes two attacks.

Glass Longsword. Melee Weapon Attack: +10 to hit, reach 5 ft., 1 target. Hit: (1d8 + 8) damage (damage type depends on active Chaotic Flux).

Glass Javelin. Ranged Weapon Attack: +10 to hit, range 30/120 ft., 1 target. Hit: (1d6 + 8) damage (damage type depends on active Chaotic Flux).

Second Wind. Cheshire has a limited well of stamina that he can draw on to protect himself from harm. On his turn, he can use a bonus action to regain hit points equal to 1d10 + 7. Once he uses this feature, he must finish a short or long rest before he can use it again.

Quick Toss. As a bonus action, Cheshire can expend one superiority die and make a ranged attack with a weapon that has the thrown property. He can draw the weapon as part of making this attack. If he hits, add the roll of the superiority die to the weapon’s damage roll.

Silvery Barbs.

Cheshire has 2 legendary actions that can only be used at the end of another creature's turn. These legendary actions recharge at the end of each round, whether he has used them all or not.

Glass Longsword (Costs 1 Action). Cheshire makes one attack with his glass longsword.

Glass Javelin (Costs 1 Action). Cheshire makes on attack with his glass javelin.

Nova of Insanity (Costs 2 Actions). Cheshire releases a burst of maddening energy in a 20-foot radius sphere centered on himself. Any creature subjected to this burst must make a DC 16 Charisma saving throw. On a failed save, the creature takes 4d6 psychic damage as a jumble of insane thoughts and images slam through its mind and it is also under the effect of Cheshire's Aura of Madness, regardless of whether it had previously succeeded on that save. On a successful save, the creature takes half as much damage and isn't under the effects of the Aura of Madness.

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