The Highwayman

The life of a highwayman is full of thrills, desperation and danger. All sorts of bad characters can be found on the road, and for one reason or another, you've joined this lifestyle. A volatile mix of allure and violence makes your victims frightened, charmed (or a little bit of both) and bit poorer than they were before you came into their lives. Your legend spreads amongst the common people, yet you must constantly be wary of betrayal and on the lookout for the authorities finally catching up to you.

Your spellcasting modifier is Charisma. Your save DC for spells and highwayman abilities is 8 + Your Proficiency Bonus + Your Charisma Bonus.

 

Trained Eye

You have a discerning eye for valuables, it is how you make your living after all! The experience you have unburdening folks of their riches allows you to make an educated guess as to where they may hide any precious items worth taking. Any investigation checks you make to look for valuable items (jewelry, coin, fine clothes, etc.) are rolled with advantage.

"Stand and Deliver"

Your legend is rising. The locals tell stories about you, romanticizing you for your charm and embellishing your nefarious deeds. Adept though you are at highway robbery, these tales further help you control the various social situations you find yourself in while you plunder, deescalate, parlay, and even woo your targets. You do, however find yourself to be more recognizable at the local taverns and places of gossip if you don't take care to disguise yourself.

Up to a number of times per day equal to your Charisma Modifier, you may try to charm or frighten creatures within a 15 foot radius as a bonus action. They must make a wisdom saving throw equal to or higher than 8 + Your Proficiency Bonus + Your Charisma Modifier. You regain all expended uses on a long rest.

Creatures may try to save again from either condition at the end of each turn. Any damage they take, or attacks against them will end the condition.

At level 17, when using the Stand and Deliver feature, in addition charm and frighten, you gain the choice to stun a number of chosen creatures equal to your proficiency bonus that are within your Stand and Deliver radius.  Creatures you target must make a wisdom saving throw. The save DC on this is 8 + Your Proficiency Bonus + Your Charisma Modifier. Creatures that fail the save become stunned until the end of your next turn. A stunned creature cannot take actions or reactions, can't move and can speak only falteringly. The creature(s) automatically fail Strength and Dexterity throws. All attacks against the creature(s) are at advantage.

 

"...Or I Shoot"

You've chosen (as your DM allows) to become trained in using the pistol weapons. A showy and dazzling weapon, yet frightening, this allows you to tap into your dastardly side, and as a result are adept at frightening your targets.

You gain proficiency with pistols. You may add your proficiency modifier to any attack rolls made with pistols. If you are brandishing a pistol and attempt to frighten creatures in a 15 foot radius, you may use your reaction to subtract 1d6 from one of the creature's rolls on the turn you attempt to frighten them (it can't be used as they continue to make saves to end the condition after they've already been frightened). This can be done after the roll is made, but before you know the result.

"...You Careless Donkey"

You've chosen to hone your skill in manipulating high stakes situations with your words.

You gain the Vicious Mockery Cantrip. Your save DC is 8 + Your Proficiency Bonus + Your Charisma Modifier. On a failed wisdom save, the target creature takes psychic damage (as specified in the spell description) and has disadvantage on the next attack roll it makes before the end of its next turn.

On a failed save, if the target is traveling with at least one other creature, for the following 1 minute, you have advantage on your next persuasion or intimidation roll targeting the other creature(s), due to their disdain or secondhand embarrassment for their mocked companion.

Knight of the Road

Long days in a saddle have given you a deep connection with your mount, and nights on the road have given you experience in surviving without the comforts of a warm bed (and sometimes on the run). You make a life on the road look glamorous, but you've just got the instincts to survive under the radar.

Beginning at 9th level, you have advantage on Survival and Stealth checks to navigate the roads and conceal your presence while traveling. You also gain a +5 bonus to your passive perception during a short or long rest on the road.

Additionally, at 9th level, you gain proficiency in the Animal Handling skill, as well as the ability to cast Find Steed, however the creature retains its beast type rather than changing to celestial, fey, or fiend. You regain the ability to use this feature after finishing a long rest. While you are mounted and aren’t incapacitated, you gain the following benefits:

• You have advantage on any ability checks made to control or maneuver a mount.
• You don't need advantage on attack rolls to benefit from your sneak attack while mounted.
• Your mount benefits from any action taken using the Cunning Action feature you use.
• You only use 10 feet of movement to mount or dismount, rather than half.

Lie in Wait

At 13th level, you excel in controlling the fighting grounds and ambushing your opponents.

Once per day, you are able to spend 1 hour preparing and scouting the terrain of an area up to 1 mile to optimize you and your allies' strategies. After doing so the following effects occur:

• Any foes that trigger any magical or physical traps in the 1 mile area you or your allies set up during this hour have disadvantage to spot the traps, and disadvantage on the first saving throw made against a trap.
• All creatures have disadvantage on Sleight of Hand, Stealth, Investigation, Perception and Survival checks to spot you, or any items you have hidden within the 1 mile area.

 

Power and Finesse

At 17th level, your time on the road has taught you to seize every opportunity to get an upper hand on your targets. You have learned to strike first with power, and maneuver yourself around the battlefield to attack and dodge at every opportune moment with great finesse.

When rolling initiative, double your Dexterity Modifier when adding it to the roll.

When you attack and hit a creature that is surprised, it must make a Constitution saving throw DC 8+ Your Proficiency Bonus + Your Dexterity Modifier. On a failed save, double the damage of your attack against the creature.

You can take 2 reactions each round, and you can take an attack of opportunity when an opponent attacks and misses you.

 

 

Stand and Deliver Upgrade

At level 17, when using the Stand and Deliver feature, in addition charm and frighten, you gain the choice to stun a number of chosen creatures equal to your proficiency bonus that are within your Stand and Deliver radius.  Creatures you target must make a wisdom saving throw. The save DC on this is 8 + Your Proficiency Bonus + Your Charisma Modifier. Creatures that fail the save become stunned until the end of your next turn. A stunned creature cannot take actions or reactions, can't move and can speak only falteringly. The creature(s) automatically fail Strength and Dexterity throws. All attacks against the creature(s) are at advantage.