Highwaymen

Not all fights are fair. Not all quests are honorable. While some mercenaries and adventurers seek out excitement, fame, fortune, and the betterment of the world, some see it as just another paying job. If this sounds like you, then the life of highwaymen might be just what you're looking for.

Most people in the highwaymen line of work don't make it very long. Those others would call bandits tend to not be bogged down by the moral stances of quests and choose whichever jobs seem easiest or best suit them, although there can always be exceptions. To survive the life of a Highwayman long, you must prove yourself cunning, versatile, and able to hold your own in battle.

 

CREATOR NOTES:

This isn't meant to be a power build, but rather a more martial rogue subclass than others. The build's original inspiration was the idea of a rogue trying to deceive others into thinking he's a fighter.

Trained Opportunist

You've had to learn to make use of any gear you can get your hands on. As a result , you've learned to be proficient in all martial weapons as well as medium armor and shields.

Aggressive Assault

Sometimes you just need to keep hitting them. When you choose this subclass, if you use the attack action, you can also attack using your bonus action.

Experienced Killer

You've been honing your abilities longer than most in your line of work to the point that killing is more of an art form for you. Starting at 9th level, you can now apply your sneak attack damage to any type of attack action you have proficiency with. You must still follow any other requirements for using sneak attack.

Elite Status

You've been honing your abilities longer than most in your line of work, and your demeanor and body language makes it obvious to others. Starting at 13th level, you have advantage on intimidation skill checks to convince others that fighting you is not worth the risk.

Merchant of Death

Few among your kind are as skilled in the art of killing, and your reflexes have become honed to it. At 17th level, whenever your attacks drop an opponent to 0 hit points, you can continue your assault, gaining an additional attack action for that turn.