The Fool

You've honed your own form of stratagem, bizarre bordering on near insanity and worst of all, nearly all of your tactics are spontaneous. Those who fall under this moniker are often impatient spies, hired killers who lack subtlety or schemers that would rather live in the moment than to meticulously plan everything. As a result you've found yourself isolated from most forms of criminal connections, most finding you either unreliable or too difficult to reign in. 

Inadvisable Initiative

Starting at 3rd level, you race into battle with wild abandon wishing to make the first move no matter the cost. You can add give yourself a bonus to your initiative rolls equal to your proficiency bonus.

Flippant Demeaner

When you choose this archetype at 3rd level, you gain proficiency in with the forgery kit, disguise kit and two gaming sets of your choice.
Additionally, you gain proficiency in one skill. Your proficiency bonus is doubled for any ability check you make using the chosen skill.

Schemer's Prerogative

Starting at 9th level When you take the Attack action on your turn, you can use a bonus action to direct one of your companions to strike an enemy's weak point. When you do so, choose a friendly creature who can see or hear you. That creature can immediately use its reaction to make one weapon attack against what you targeted with your attack action, adding the proficiency bonus to the attack's damage roll.

Masterful Improvisation

Starting at 13th level, you find able to get out of even the most unfortunate of circumstances.

Upon failing a saving throw or attack roll you may use your reaction to reroll your d20 keeping the higher of the two results.

Devil's Whim

You harness the sheer unpredictability of the world and harness it to ensure your continued success.

You have elusive points in the form of 1d10s equal to your dexterity modifier (minimum of 2). Whenever you, an ally or an enemy makes an attack roll, ability check or a saving throw, you can spend one or more elusive points to reduce or increase the value rolled. 

If more than one creature spends a elusive point to influence the outcome of a roll, the points cancel each other out; no d10s are rolled.

You regain your expended luck points when you finish a long rest.