Fraudster, cheat, scammer, shyster… to be a confidence trickster is to alienate yourself from society one gullible mark at a time. However, as the saying goes, “you can’t cheat an honest man”, so they probably deserved it, right? Plus, pulling off a perfectly planned scam can be so fun.
Charlatans are masters of planned deceit and misdirection. A Charlatan might prepare several disguises and waltz into a jewellery store, wait for a perfectly timed explosion to distract the proprietor, then replace a priceless tiara with a poorly-forged replica. Hot-footing it out the door, the Charlatan might switch outfits quicker than the proprietor can say “Oh my word, where’s that priceless tiara I tricked a down-on-her luck noble into selling for a pittance?”. The Charlatan might then direct the pursuing, nonplussed guards into a side alley, before fencing the heirloom and heading to a bar to celebrate a job well done.
In combat, Charlatans appear as harmless bystanders before using concealed weapons to surprise foes, striking with devastating consequences.
Conning is like cooking, and a trickster’s tools are the ingredients with which they cook up a plot, creating delectable morsels that the gullible are all too keen to consume. You gain proficiency with the disguise kit and your choice of the forgery kit or any artisan’s tools. When you reach 9th, 13th, and 17th level in this class, choose another tool from this list with which to gain proficiency.
In addition, you have advantage on any ability checks made to find a willing buyer for your purloined or otherwise misappropriated goods.
Long sleeves and concealed pockets turn a Charlatan into a walking inventory of hidden paraphernalia. When you have a free hand and take the Attack action, you can turn one attack against a creature into a special hidden weapon attack using a weapon concealed upon your person. To do so, the weapon must have the Thrown and Finesse properties. When you do so, make a Dexterity (Sleight of Hand) check against your target’s passive Perception score. On a success, you make the attack roll with advantage.
Teamwork makes the scheme work, a Charlatan can achieve much more as part of a team. Starting at 9th level, if you succeed on this Dexterity (Sleight of Hand) check by 10 or more, the target becomes confused and the next attack roll against it by a creature other than you before the start of your next turn has advantage.
At 17th level, any number of attacks you make can be turned into a hidden weapon attack, instead of only one when you take the Attack action, provided the weapon has the Thrown and Finesse properties.
The ability to play multiple roles, and switch between them on the fly, expands the repertoire of scams a Charlatan can undertake. When you finish a long rest and you have a disguise kit, you can prepare a number of personas equal to your Intelligence or Charisma modifier (minimum 1). These personas are replete with mannerisms, accents, quick-change costumes, and even different smells. They can have different clothing and other belongings, they can seem 1 foot shorter or taller than you, and they can appear thin, fat, or in between.
Quick Change, as an action, you can change into one of your personas. So long as a creature can’t see you when you take this action (for example, if you are hidden or behind opaque total cover), the creature doesn’t recognise you as the same person when it sees you in your new persona. If a hostile creature can’t fathom how you might have escaped, it is likely to be suspicious of you, even in your new persona. A creature can use its action to inspect your appearance, discerning your disguise if it succeeds on an Intelligence (Investigation) check (DC equals 8 + your proficiency bonus + your Intelligence or Charisma modifier). A very suspicious creature may detain you anyway, and a creature inclined to violence (such as a hunting owlbear) will likely continue to attack despite any apparent difference in appearance.
You can give yourself a bonus to your initiative rolls equal to your Intelligence or Charisma modifier. In addition, when you succeed on your Hidden Weapons ability check, you score a critical hit on a roll of 19 or 20 on the d20.
You are a master of appearing harmless. When you roll initiative, until an enemy observes you making an attack, dealing damage to another creature, or casting a spell that affects a creature other than you, it considers you harmless. While it views you this way and it can see at least one other creature that it is hostile towards, it must first succeed on a Wisdom saving throw before it can target you with an attack or other effect (DC equals 8 + your proficiency bonus + your Intelligence or Charisma modifier).
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