(OpenAI's chatGPT machine learning thingo generated almost all of this class, and I mostly just edited it together.)
The Trickster
As a Trickster, you are a veritable virtuoso of deception and misdirection. With your cunning wit and nimble fingers, you can outsmart and outmaneuver even the most formidable of foes. Your clever tricks and elaborate illusions leave your enemies bewildered and confused, while your quick reflexes and agility allow you to escape danger with ease. Whether you're using your magic to deceive and mislead, or manipulating your surroundings to your advantage, you are a master of trickery and deception.
Ability Scores: Your Charisma should be your highest ability score, followed by Dexterity. Charisma is important for spellcasting and for your abilities that rely on deception, while Dexterity is important for your abilities that rely on agility and quick reflexes.
Hit Points
Hit Dice: 1d8 per Trickster level
Hit Points at 1st Level: 8 + your Constitution modifier
Hit Points at Higher Levels: 1d8 (or 5) + your Constitution modifier per Trickster level after 1st
Proficiencies
Armor: Light armor
Weapons: Simple weapons
Tools: Disguise kit, thieves' tools
Saving Throws: Charisma, Dexterity
Skills: Choose three from Acrobatics, Deception, Perception, Persuasion, Sleight of Hand, Stealth
Equipment:
You start with the following equipment, in addition to the equipment granted by your background:
(a) two daggers or (b) a quarterstaff
(a) a light crossbow and 20 bolts or (b) an unspecified number of darts, so many darts, more darts than you'll ever need
(a) a dungeoneer's pack or (b) a burglar's pack
Leather armor, thieves' tools and a disguise kit
Class Features:
Bag of Tricks: At 1st level, you gain access to the Minor Illusion cantrip. If you already know this cantrip, you learn a different wizard cantrip of your choice. You know the spells Disguise Self and Nondetection, and always have these prepared, and can cast these without using a spell slot.
At 2nd level, You learn the following additional spells, they are always prepared, and you can cast them without using a spell slot: Grease, Shatter, and Silence.
Charisma is your Spellcasting Ability for these Trickster Spells.
Cunning Action: At 2nd level, your quick thinking and agility allow you to move and act quickly. You can take a bonus action on each of your turns in combat. This action can be used only to take the Dash, Disengage, or Hide action.
Opening Gambit: At 4th level, You have a keen sense for danger and are able to react quickly when things turn to blows. You can add your Charisma modifier to your initiative rolls. When you roll initiative, you can switch positions with another willing creature within 30 feet of you, so long as you and that creature could reasonably have been able to move between these positions on your turns, ignoring opportunity attacks.
Uncanny Dodge: Starting at 5th level, when an attacker that you can see hits you with an attack, you can use your reaction to halve the attack's damage against you.
Simply Not Being There: At 7th level, you gain the ability to teleport short distances as a bonus action. This ability has a range of 30 feet and can be used once. You regain your use of this ability whenever you finish a short or long rest.
Unbelievable Resilience: At 8th level, You are difficult to catch and even harder to kill. You have resistance to bludgeoning, piercing, and slashing damage, and can use your reaction when attacked or when forced to make a Dexterity save to take the Dodge action, causing disadvantage on the triggering attack or save.
Spirit of Pure Chicanery:
At 10th level, you gain the ability to transport yourself and others short distances instantly. As an action, you can cast the Dimension Door spell without using a spell slot. When you cast Dimension Door you can bring along additional creatures within 30 feet. You can bring as many creatures as your Charisma bonus. You can use this ability once per long rest.
At 11th level, you gain the ability to turn invisible. As a bonus action, you can cast the Invisibility spell on yourself without using a spell slot. This effect lasts until you attack, cast a spell or end a long rest, with no duration. You can use this ability once, and regain your use of this ability whenever you finish a short or long rest.
At 12th level, You gain the ability to confuse and disorient your enemies. As an action, you can cast the Confusion spell without using a spell slot. This spell affects all hostile creatures within 30 feet of you, forcing them to make a Wisdom saving throw vs your Charisma spell save DC or become confused for 1 minute. You can use this ability once per long rest.
Subclass: The Fool
As a Fool, you are a master of deceit and manipulation cloaked in carefree revelry and frivolous fun. With your quick wit and playful spirit, you can entertain and amuse even the most jaded of souls, all the while concealing your true nature as a cunning and ruthless trickster. Your simple jokes and silly pranks bring laughter and joy to those around you, while your sly tongue and cunning mind deceive and mislead even the most perceptive of individuals. Though others may see you as a harmless jester, they would be wise not to trust you, for you are a dangerous and ruthless foe, skilled in the art of deception and manipulation. You may not be the most cunning or clever of individuals, but that does not concern you - for you are a master of carefree revelry and ruthless mischief.
Fool's Luck: At 3rd level, you have the ability to manipulate luck in your favor. You can reroll any of your failed ability checks, attack rolls, or saving throws, rolling a single extra die. You must use the new roll. You can use this ability a number of times equal to your Charisma modifier (minimum of 1) per long rest. If you roll a 1 on your Fool’s Luck die, you take 1d6 psychic damage.
Creature of Pity: At 3rd level, you gain the ability to manipulate the emotions of others. As an action, you can force a creature within 60 feet of you to make a Wisdom saving throw. On a failed save, the creature is filled with pity for you and will not attack you or target you with harmful spells or abilities for 1 minute.
Fool's Errand: At 6th level, you gain the ability to send a creature on a wild goose chase. As an action, you can force a creature within 30 feet of you to make a Wisdom saving throw vs your Charisma spell save DC. On a failed save, the creature must move in a random direction for 1 minute or until it is attacked or otherwise significantly inconvenienced. During this time, the creature will not attack or interact with any other creatures.
Fool’s Sympathy: At 9th level, whenever you miss with an attack that targets one creature, or when one of your spells or abilities that asks for a saving throw and targets one creature fails, you can choose another creature within range that the attack or effect can target. Repeat the attack or save against that creature, and resolve the effects as though they were a target of that attack or effect.
Vile Unchecked Descent into Chaos: At 13th level, you gain the ability to take a calculated risk to turn the tide of battle in your favor. As a bonus action, you can force all creatures within 60 feet of you to make a Wisdom saving throw vs your Charisma spell save DC. On a failed save, the creatures must attack the nearest creature (including their allies) for 1 minute.
Subclass: The Dart Master
As a Dart Master, you are a deadly assassin, striking fear into the
hearts of your enemies with your precise and deadly darts. With your
quick reflexes and agile movements, you can effortlessly dodge and weave
through the battlefield, unleashing a hail of deadly missiles on your
foes. Your cold, calculating demeanor belies a ruthless and efficient
killer, striking without warning and leaving no survivors. Your mastery
of the dart allows you to take down even the most formidable of enemies
with ease, making you a feared and respected opponent on the
battlefield. You are a deadly predator, stalking your prey with the
skill and precision of a true master of the dart.
Dart Virtuoso: At 3rd level, you can throw two darts as a single attack, and you can add your Charisma modifier to the damage of each dart you throw. You can use darts to make ranged weapon attacks with a range of 40/120 feet.
Really Good at Darts: At 6th level, your darts are considered magical for the purpose of overcoming resistance and immunity to non-magical attacks and damage. On a turn where you take the Attack action, you can throw two darts as a bonus action.
Mosquito Style: At 9th level, your darts develop an unquenchable vampiric thirst. Whenever you roll a 1 on a damage die for a dart attack, you can recover 1d4 health.
I Only Need One: At 13th level, You can unleash a devastating strike with a single dart. As an action, you can make a ranged weapon attack with a dart against a creature. This also spends your bonus action. This dart attack has an additional +10 bonus to the attack roll and deals 10d4 piercing damage on a hit as well as 5d4 psychic damage. If the target is hit by this attack, it must make a Constitution saving throw against your spell save DC or be stunned until the end of its next turn. In addition, the target must make a Wisdom saving throw against your spell save DC or be frightened of you until the end of its next turn. Creatures that are immune to the frightened condition that fail this save are frightened as though they were not immune.
