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 the animal handling skill and mounted combatant feat.

While you are mounted and aren’t incapacitated, you gain the following benefits: You have advantage on melee attack rolls against any unmounted creature that is smaller than your mount. You can force an attack targeted at your mount to target you instead. If your mount is subjected to an effect that allows it to make a Dexterity saving throw to take only half damage, it instead takes no damage if it succeeds on the saving throw, and only half damage if it fails.

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 now have +2 perception while on nightwatch.

Parlay

At 9th level, You are able to better control the situations you find yourself in. Should you choose to negotiate on some matter you'll always have advantage on ability checks involving deescalation, surrender, or payment.

Stomping ground

At 13th level, you are able to spend a day's work scouting out the terrain of an area and optimazing your criminal strategies accordingly. You gain +3 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) tests 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.

At 17th level, you may instead designate an entire city or a biome such as forests, mountain ranges or a stretch of coastline as your stomping ground, provided that you have spent a great deal of time in that area already.

Making an example

At level 17, whenever you score a critical hit, the two nearest enemies that can see you must make a wisdom saving throw (DC = 7 + your dex + proficiency). 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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