Highwayman

You have spent your life on the road, scratching a living out of whatever you can find, from whoever you can find. There's no honour amongst thieves, but maybe you can help each other make a little extra coin. 

Save DC. Some of your Highwayman abilities call for a Saving Throw, any time this is the case, the DC for the Saving Throw is equal to 8 + Your Proficiency Bonus + Your Charisma Bonus.

After a Prize

You have spent years honing your craft, you can slip almost any item away into your pocket with ease. After reaching level 3 in this class, you gain Advantage on Sleight of Hand checks. 

Firearms User

You have trained and trained with your Pistol, it’s now second nature to have it in your hand. You gain proficiency with Pistol weapons, you may add your Proficiency Bonus to attacks made with Pistols.

Stand and Deliver!

Highwaymen have a fearsome reputation, your name sends a shiver down the spine of your enemies. After reaching level 3 in this class, as a bonus action you express a shout, all hostile creatures within 10ft. must succeed a Charisma saving throw or be Frightened until your next round.

You can use this feature a number of times equal to your Charisma modifier (minimum of 1). You regain all expended uses on a long rest.

On My Mark!

You call upon your allies to gang up on a creature, marking it for it’s inevitable demise. After reaching level 9 in this class, you may use your bonus action to mark a target, when marked in this way, attacks against the creature gain advantage until your next round.

You can use this feature a number of times equal to your Charisma modifier (minimum of 1). You regain all expended uses on a long rest.

Open a Vein

Your instincts tell you where a weak point is, and you make a strike against it. After reaching level 13 in this class, as an action, you can use a weapon attack force the creature to take a Constitution Saving throw, on a failed save, the creature has disadvantage on Attacks and Ability Checks until your next round.

You regain expended uses of this feature on a short or long rest.

Highway’s Bane

Your status as a Highwayman is legendary, your name is known far and wide to be feared. After reaching level 18 in this class, creatures making any saves against your Rogue abilities do so with Disadvantage. Additionally, once per short or long rest, your Sneak attacks deals an additional 3d6 damage.