Highwayman (5e Subclass)

The highwayman

A highwayman gettin' that paper.

A Highwayman is typically a roadside robber who ambushes travelers in the 1800s on horseback. This sort of lifestyle involves a great deal of patience and negotiations. A rogue willing to partake in this kind on banditry does not necessarily need the use of a horse to do it so but it is thematically correct and the use of mounts is a true status symbol that separates the highwayman from a common bandit.

Highway Horsemanship

At 3rd level, you gain proficiency in the Animal Handling skill. In addition, while you are mounted and aren’t incapacitated, you gain the following benefits:

• You can mount or dismount spending 5 feet of movement, instead of half.
• 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.

King of Stakeout

At 3rd level, your many hours of lying in wait for targets has granted you skill in the ever esteemed field of stakeout. You have a +5 bonus on your passive Wisdom (Perception) checks made during your short or long rest.

Parlay

At 9th level, you are able to better control the situations you find yourself in. You have advantage on Intelligence, Wisdom and Charisma checks involving deescalation, surrender, or payment.

Stomping Ground

At 13th level, you are able to spend 1 hour scouting out the terrain of an area and optimizing your criminal strategies accordingly. At the end of that hour, an area of 1 mile becomes your stomping ground. Alternatively, if you spend 24 hours, you can instead designate an entire city or a biome such as forests, mountain ranges or a stretch of coastline as your stomping ground.

You gain Advantage to initiative rolls while in the stomping ground and all creatures have disadvantage on Dexterity (Sleight of Hand), (Stealth), Intelligence (Investigation), or Wisdom (Perception), (Survival) checks meant to locate or hide from you, or to locate any items or goods you have hidden or stashed in the area.

You cannot have more than one stomping ground at a time.

Making an Example

At 17th level, whenever you score a critical hit, the two nearest enemies that can see you within 30 feet must make a wisdom saving throw (DC = 8 + your Dexterity modifier + your proficiency bonus). On a failure, they are frightened of you for 1 minute. An affected creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

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