Name: Jesse Proudfoot
Race: Halfling
Size: small
Alignment: Chaotic good
level/Class/archetype: 20 Rogue (mastermind)
Gold: 1291

STR: 8/8 -1
Dex: 20/20 +5
Con: 14/14 +2
INT: 15/15 +2
WIS: 16/16 +3
Cha: 16/16 +3
Proficiency bonus: +6

Initiative: +5
HP: 142/142 (20d8+40)
HD rolled: 0
Armor class: 17 (5 dex, +2 +1 studded leather armor)
Speed: 25 feet
Effects:

Saving throws: Dex: +11, Int: +8, Wis: +9
Death saving throws: 0 made | 0 failed

Senses: Passive Perception: 13
Proficiencies:
quick Skills: Acrobatics, deception, investigation, performance, slight of hand, stelth
Equipment: Light armor, Simple weapons, hand crossbows, longswords, rapiers, shortswords
Toolsets: Thieves tools, Disguise kit, forgery kit 3 dragon ante (dice)
Expertese: Acrobatics, Deception, disguise kit, slight of hand, stealth

Languages: Common, Halfling

Skills: Most common ability score; proficient, total
Animal Handling: Wis; +3
Arcana: Int; +2
Athletics: Str; +-1
Acrobatics: Dex; +17
Deception: Cha; +15
History: Int; +2
Insight: wis; +3
Intimidation: Cha; +2
Investigation: Int; +8
Medicine: Wis; +3
Nature: Int; +2
Perception: wis; +3
Performance: Cha; +9
Persuasion: Cha; +3
Religion: int; +2
Sleight of Hand: dex; +17
Stealth: Dex; +17
Survival: Wis; +3

Personality:
Traits:
1: Flattery is my MO, think car salesman.
2: I have multiple holy symbols for multiple situations.
Ideal:
1: Friendship is what is most important to me.
Bond:
1: I kind of well, let's just say Majistrate Dailynth in Jeck's crossing is not happy with me. I ran a scam with my pal Cardasean, and stole from the town treasury. It didn't help that he and I have broken out of the prison three times already.

Flaw:
I can't resist swindling people who think they are more powerful than me.
I'm afraid of running water.

Background features:
Scam: I put on new identities like clothes.
False Identity: You have created a second identity that includes documentation, established acquaintances, and disguises that allow you to assume that persona. Additionally, you can forge documents including official papers and personal letters, as long as you have seen an example of the kind of document or the handwriting you are trying to copy.

Racial features:
Dexterity bonus increased by +2.
Lucky: When you roll a 1 on the d20 for an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll.
Brave: You have advantage on saving throws against being frightened.
Lightfoot halfling:
Charisma bonus increase by +1.
Halfling Nimbleness: You can move through the space of any creature that is of a size larger than yours.
Naturally Stealthy: You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

Class Features:
Expertese: Choose 2 skills or 1 skill and thieves' tools and double proficiency bonus.
Sneak attack (10d6): Once per turn, if you have advantage on the attack roll, or they are threatened by an ally within 5 feet and you don't have disadvantage on the attack roll.
Thieves' cant: Conversation which takes four times longer to convey information than normal speech.

2nd level:
Cunning Action: You can dash, disengage, and hide as a bonus action.

3rd Level:
Mastermind archetype:
Master of Intrigue
When you choose this archetype at 3rd level, you gain proficiency with the disguise kit, the forgery kit, and one gaming set of your choice. You also learn two languages of your choice.
Additionally, you can unerringly mimic the speech patterns and accent of a creature that you hear speak for at least 1 minute, enabling you to pass yourself off as a native speaker of a particular land, provided that you know the language.

Master of Tactics
Starting at 3rd level, you can use the Help action as a bonus action. Additionally, when you use the Help action to aid an ally in attacking a creature, the target of that attack can be within 30 feet of you, rather than 5 feet of you, if the target can see or hear you.

4th Level:
Master Of Disguise
You have honed your ability to shape your personality and to read the personalities of others. You gain the following benefits:
Increase your Charisma score by 1, to a maximum of 20.
You gain proficiency with the disguise kit. If you are already proficient with it, you add double your proficiency bonus to checks you make with it.
If you spend 1 hour observing a creature, you can then spend 8 hours crafting a disguise you can quickly don to mimic that creature. Making the disguise requires a disguise kit. You must make checks as normal to disguise yourself, but you can assume the disguise as an action.

5th level:
Uncanny Dodge: 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.
7th level:
Evasion
Beginning at 7th level, you can nimbly dodge out of the way of certain area effects, such as an ancient red dragon's fiery breath or an ice storm spell. When you are subjected to an effect that allows you to make a Dexterity saving throw to take only half damage, you instead take no damage if you succeed on the saving throw, and only half damage if you fail.

9th level:
Insightful Manipulator: If you spend one minute outside of combat interacting with or observing a creature, you can learn whether the creature is less or more intelligent, wise, charismatic, of lower or higher level, or find out a personality trait or historical fact about the creature.

10th level:
Fighting initiate (two-weapon fighting)
Your martial training has helped you develop a particular style of fighting. As a result, you learn one Fighting Style option of your choice from the fighter class. If you already have a style, the one you choose must be different. Whenever you gain a level, you can replace this feat’s fighting style with another one from the fighter class that you don’t have.

11th level:
Reliable talent: If you add your proficiency bonus to an ability check, treat a 9 or lower as a ten.

12th level:
Piercer: Increase your Strength or Dexterity by 1, to a maximum of 20.
Once per turn, when you hit a creature with an attack that deals piercing damage, you can re-roll one of the attack’s damage dice, and you must use the new roll.
When you score a critical hit that deals piercing damage to a creature, you can roll one additional damage die when determining the extra piercing damage the target takes.

13th level:
Misdirection: Beginning at 13th level, you can sometimes cause another creature to suffer an attack meant for you. When you are targeted by an attack while a creature within 5 feet of you is granting you cover against that attack, you can use your reaction to have the attack target that creature instead of you.

14th level: blindsense: Starting at 14th level, if you are able to hear, you are aware of the location of any hidden or invisible creature within 10 feet of you.

15th level:
Slippery mind: Gain proficiency with Wisdom saving throws.

16th level:
Tandem Tactician: Help range is 40 feet, and can help two allies at once.
17th level:
Soul of Deceit
Starting at 17th level, your thoughts can't be read by telepathy or other means, unless you allow it. You can present false thoughts by making a Charisma (Deception) check contested by the mind reader's Wisdom (Insight) check.
Additionally, no matter what you say, magic that would determine if you are telling the truth indicates you are being truthful if you so choose, and you can't be compelled to tell the truth by magic.

18th level:
Elusive: Nobody has advantage against you unless incapacitated.
19th level:
Defensive Duelist: When you are wielding a finesse weapon with which you are proficient and another creature hits you with a melee attack, you can use your reaction to add your proficiency bonus to your AC for that attack, potentially causing the attack to miss you.
20th level:
Stroke of luck: Turn a missed attack into a hit or cause an ability check to be a 20 once per short rest.

Attuned items:
1: Armor, gives stealth on advantage
2: cloak of displacement: Attacks have disadvantage on you until you get hit, renews every round.
3: Winged boots: can fly for up to four hours, must use one minute at a time. regains 2 hours every 12 hours.
Equipment: Leather armor, 2 shortswords, shortbow, Quiver containing 20 arrows, two daggers in wrist sheathes
Inventory: Backpack, a bag of 1000 ball barings, 10 feet of string, Bell, 5 candles, crobar, Hammer, 10 pitons, a hooded lantern, 2 flasks of oil, 5 days rations, tinderbox, waterskin, 50 feet of hemp rope, disguise kit, thieves' tools, 2 potions of cure wounds (2d4+2) 2 greater potions of cure wounds (4d4+4)

Actions:
Shortsword: +12, 1d6+6
Shortbow: +12, 1d6+6
dagger: +12, 1d4+6, range=20 or 60 ft

Reactions:
Uncanny Dodge: 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.
Redirection: When covered by another, you can redirect an attack that would hit you against your covering target.
Defensive duelist: Add +6 to ac against one attack.

Bonus Actions:
shortsword: +12 1d6+6
Dagger melee or thrown: +12 1d4+6, range: (20 - 60 ft)
Dash, Disengage, hide, help (40 ft within sight or sound), for two allies.