Busker

Street performers of "magic," Buskers excel so much at sleight of hand and misdirection that onlookers swear they are witnessing real magic. For a Busker, a little bit of preparation, smoke, and mirrors goes a long way. Buskers use their party tricks to charm, distract, and--at the point of the show when the audience realizes they've been snookered or even pickpocketed--escape.

Convincing Tricks

You have the ability to use Playing Cards or Thieves' Tools (which for you include the typical magician's tools of cups and a ball, nearly invisible string, an old top hat, etc.) to perform a "magic" trick as an Influence action. When doing so, make a Dexterity (Sleight of Hand) or Charisma (Performance) check. This Skill Check is to determine how well you pull off the act; the onlooker may choose to also perform a Wisdom (Insight) check to discover that you have played a trick on them, even if they don't understand how, or (if they already suspect trickery) a Wisdom (Perception) check to figure out how you did it. The DC for these is the DC of the trick you performed + your Dexterity or Charisma bonus (depending on if you used Sleight of Hand or Performance) + your Proficiency Bonus. If their passive Insight or Perception already meets this DC, they do not need to make this Skill Check.

Easy trick. Easy tricks are the simple flourishes of the "pick a card" or "which cup has the ball?" variety. Expertly pulling a coin out of someone's ear can be impressive for the simple-minded, but not as much for those with more sophistication. Using an Easy trick you can make the smallest Tiny objects (no larger than a closed fist) "disappear" by forward or reverse palming it or sliding it up your sleeve. There is a DC 10 to succeed. On a success, any onlooker has their guard slightly lowered and they have a penalty of -1 to Wisdom (Insight) and Wisdom (Perception) checks against you for the next five minutes. This penalty does not stack with itself, but it does stack with other Convincing Tricks and Busker features.

Medium trick. These are more difficult to pull off, but also more rewarding. With a Medium trick you could apparently destroy and restore a Tiny object that is no larger than a tankard, make it appear, "transport" it, or secret it away into a pocket, under a hat, ir into a bag or compartment near you. Most people are impressed by a well-executed Medium trick. There is a DC 13 to succeed. On a success, any onlooker has Disadvantage on Wisdom (Insight) and Wisdom (Perception) checks against you for the next hour.

Challenging trick. It is risky to attempt a Challenging trick. They can involve the appearance/disappearance or other manipulation of any Tiny objector creature, including those being touched by, in possession of, or worn by an observer. Pulling a rabbit out of a hat, hatching a dove from a ball, or turning an end table into a cat are examples of Challenging tricks. There is a DC 16 to succeed. On a success, any onlooker's attitude towards you improves one level (Hostile to Indifferent or Indifferent to Friendly).

Those affected by your Convincing Tricks are all who can see them within a 5 ft. Emanation originating from you. This Emanation increases with your Rogue level: 5 ft. at 3rd level, 10 ft. at 6th level, 15 ft. at 9th level, 20 ft. at 13th level, 25 ft. at 17th level, and with an unlimited range (as long as your trick can be observed) at 20th level. The DM determines the affect your tricks have on any who observe them but are outside of this emanation (keeping in mind that the greater distance in itself makes perception and insight more difficult)

The DM can choose the consequences for failing a Convincing Trick based on the specific target, the particular trick attempted, and the circumstances. Does the person laugh at you? Do they have Advantage on Wisdom (Perception) checks to now actively seek out your sleights? Are they more hostile? Or do you simply lose all credibility with them? Whether an audience of one or many are forgiving or boo you off the stage after one or multiple failed tricks is left to the DM's discretion.

Level 3: Close-up Magic

As a Bonus Action, you can do one of the following.

Convincing Trick. Perform a Convincing Trick of any level on one target within 5 ft. of you or closer.

Is this your Wallet? Make a Dexterity (Sleight of Hand) check to pick the pocket of one creature within 5 ft. of you or closer.

On a success, in addition to any effects of the Convincing Trick, the target is temporarily baffled and has Disadvantage on any Skill Checks made against you for the next minute.

Level 3: Smoke and Mirrors

You can discretely prepare the area where you will perform a Convincing Trick for maximum effect. For every hour you spend preparing in a 30 foot cube area, you can set up mirrors, props, etc. to perform a more impressive Convincing Trick. Doing so can grant you either of the following benefits:

Spectacle. Your preparations enhance the effect of one of your tricks. You have Advantage on the Dexterity (Sleight of Hand) or Charisma (Performance) check you make to determine the success of your trick, and all those who see it within the 30 ft. cube you prepared experience the effect as if they were within your Emanation. The effect lasts twice as long as normal.

Tactical. You can trigger an effect anywhere in the 30 ft. cube to go off during combat, distracting one creature. You can either create this effect as a Bonus Action on your turn, allowing you to use Sneak Attack on the target as if an ally were within 5 ft. of it, or as a Reaction to the target's melee or ranged attack, causing it to make its Attack roll with Disadvantage.

You can only use this benefit once per hour of preparation time spent.

The setup process is usually conspicuous; if there are other people in the area they are likely to notice it. The DM can determine how you might set up in secret: taking twice the time, performing Dexterity (Sleight of Hand) checks, gaining advantage if your allies provide distractions, needing to first Hide or find Cover, or another adequate measure.

Level 9: Three Card Monte

You gain the following Cunning Strike option.

Find the Ball (Cost: 1d6). If you have the Hide action’s Invisible condition, this attack doesn’t end that condition on you if you end the turn behind Three-Quarters Cover or Total Cover. In addition, the target suspects you may be hiding behind cover in up to two other spaces within a 30 ft sphere of your actual position.

Level 13: Mentalism

You’ve learned the subtle art of incepting choices upon others, granting you the following benefits.

Pick a Number. Your speech and suggestions lead others into choosing exactly what you want them to. All Convincing Tricks that involve another to participate are automatic successes.

Rabbit Season. In any conversation, you can make a Charisma (Performance) check instead of a Charisma (Persuasion) check to convince the other person of something. Whenever you succeed, the other person is convinced the idea was theirs to begin with. This feature can be stacked with the effects of the Convincing Tricks, Close-Up Magic, and Smoke and Mirrors features.

You Wouldn't Hit a Man with Glasses. Once per round, as a Reaction to being targeted by a melee attack, or by a ranged attack if you use the Smoke and Mirrors feature, you can make a plea with the attacker if it can understand a language to change its mind. Make a Charisma (Performance) check. If the result is higher than the attacker's original attack roll, the attacker is Charmed for the next round and its attack is wasted. On a failure, it pulls its punch and deals only half damage to you. A creature can only be affected by this feature once per combat.

Level 17: Master of Misdirection

You are adept at working behind the scenes when in the spotlight, and also in the art of the escape. You can take two turns during the first round of any combat. You take your first turn at your normal Initiative and your second turn at your Initiative minus 10.

In addition, you have learned even more impressive Convincing Tricks.

Hard tricks: These are the most extreme works of prestidigitation. "Cutting" someone in half, making them "levitate", "teleporting" them from one booth to another... or yourself, for that matter: these are the seemingly impossible feats that are Hard tricks. You can move yourself or any Medium or smaller object or creature a distance away that is equal to your Speed, including objects that are closely guarded or creatures that are unwilling. You can pickpocket up to your Dexterity Bonus number of objects at once. There is a DC 19 to succeed. On a success, any onlookers are Charmed by you for the next hour.