Gumshoe/Corsair/Scallywag

As an archetypal Gumshoe, you have a knack for outwitting others with clever words and fast hands. You are a master of distraction and deception. You have a keen sense of how others move an act allowing yourself to be adaptive and tactical. Gumshoes can be anything from pickpockets to con men; whatever the profession, they will always know what to say to get what they want.

Diversion

Starting at 3rd level, as an action you can make a Charisma (Deception) check against a creature you can see within 5 feet of you that isn’t incapacitated, contested by the target’s Wisdom (Insight). If you succeed, you distract the target and can immediately make a Dexterity (Sleight of Hand) check against the creature with advantage.

Additionally, as an action you can make a Charisma (Performance) check against a creature you can see within 5 feet of you that isn’t incapacitated, contested by the target’s Wisdom (Perception). If you succeed, all creatures other than you become invisible to the target for 1 minute.

Keen Belittlement

At 3rd level, you use your words and tactics to lower an opponent's guard. As a bonus action, you can make either a Charisma (Intimidation) or Wisdom (Insight) check against a creature you can see that isn’t incapacitated, contested by the target’s Charisma (Deception) check. If you succeed, all attacks against that creature deal additional damage equal to your Sneak Attack damage until the start of your next turn.

Skillful Imitation

Starting at 9th level, as a reaction when someone makes a skill check or an attack roll, you can record the result the of die without any modifiers, you do this after the d20 is rolled. Whenever you make a skill check of the type that you recorded your die for or whenever you make an attack roll, you can replace your roll with the result you had recorded. You only use the die’s roll and your own ability modifiers. You can wait until after you roll the d20 before deciding to use this feature, but you must decide before the DM says whether the roll succeeds or fails. You can do this a number of times equal to your Wisdom modifier.You regain any expended uses when you finish a short rest.

Enticing Flings

Beginning at 13th level, your ranged attacks deceive and disable your foes. After you make a successful ranged attack you can have the targeted creature make a Dexterity saving throw (DC 8 + your Dexterity modifier + your proficiency bonus). On a failed save, they are affected by one effect of your choice from:

• The next attack against the creature has advantage.
• The creature’s speed is halved for until the start of your next turn.
• The creature has disadvantage on all attacks against creatures other than you until the start of your next turn.

Instead of choosing one of these affects you can also choose to make a second ranged attack against the creature. This attack cannot have advantage and cannot disadvantage.

Toxic Conversation

At 17th level, your words are filled with physically painful and poisonous malice. If you speak to a humanoid for at least 1 minute, you poison it with your chinwag, gabfest, or confabulation. At the end of the conversation, the target must succeed on a Constitution saving throw (DC 8 + your Charisma modifier + your proficiency bonus). On a failed saving throw the target takes poison damage equal to your Sneak Attack damage and becomes poisoned, on a successful saving throw they take half as much damage and aren’t poisoned. When you use this ability the creature has no idea that you have used it one them. 

Once you use this feature, you can’t use it again until you finish a short or long rest.