the scoundrel

for some, the only rule in life is survival, at any cost. a scoundrel fights with no regard for silly concepts like honor, or fairness. they will try anything, no matter how desperate, no matter how long the odds, if it means they can live to fight another day.

Stirke first

Scoundrels know the importance of fighting on thier terms. starting at 3rd level, you add your proficiency bonus to your initiative checks, as long as you aren't surprised.

Gambit

A scoundrel is a master of all sorts of daring, desperate acts in battle, not in the name of courage, but of self preservation. Starting at 3rd level you can take the Gambit action in combat. Typical Gambits are playing dead, faking a retreat or surrender, or convincing your enemy that you're just an innocent bystander... When you take this action, make a persuasion, deception, or performance check (your choice) contested by an insight or perception check of one creature who can see you. If you succeed, the target creature becomes less hostile towards you, and your next attack against it gains advantage. Once you make a Gambit attempt against a creature, you can not make another attempt at the same creature until after a long rest.

Making the Mark

Starting at 9th level, you become adept at picking out the weak and gullible. When you choose to make a skill check against a creature that you can see, and who can understand you, that is contested by that by that creatures Perception or Insight check, you can see the results of that creatures check, before you make your attempt. You can use this ability a number of times per short or long rest equal to your Charisma modifier.

Placating your Target

Starting at 13th level, you can use your Cunning Action to make a Gambit attempt. Additionally, you may use your Gambit feature outside of combat to make your enemies less prepared to fight. If you make a successful Gambit against a creature outside of combat, it treats its next initiative check as a 0, if you fail your attempt, it can treat its next initiative check as a 20. You may only effect one creature at a time with this ability, using it on a new creature cancels any effect it has on the first.

Just How Gullible Are You?

Starting at 17th level, you may make a Gambit attempt on any creature twice between long rests, additionally, the first attack you make on a creature you've made a succesful Gambit against, is considered a Critical Hit as long as it would hit.