Brigand

Be it a bold and brash cut-purse, a daunting highwayman, or a snarling corsair, there are many Brigands to be found in all corners of the world. Women and men cut of a more brutal and underhanded cloth tend not to stick their necks out for others, nor go on grand adventures, but there always exist the rare individuals that rise above the stereotypes of their occupation. Heroic characters that take this martial archetype may be exactly those exceptions.

Underworld Training: Tool Kit

When you take this archetype at 3rd level, you gain proficiency in your choice of thieves' tools, disguise kit, or forgery kit.

Disguise Kit

Disguise Kit Proficiency

Forgery Kit

Forgery Kit Proficiency

Thieves' Tools

Thieves' Tools Proficiency

Underworld Training: Skill

Additionally, you gain proficiency in one of the following skills of your choice: Deception, Intimidation, Sleight of Hand, or Stealth.

Deception

Proficiency in Deception

Intimidation

Proficiency in Intimidation

Sleight of Hand

Proficiency in Sleight of Hand

Stealth

Proficiency in Stealth

Dirty Fighting

Also starting at 3rd level, you learn to strike savagely at your foes' weakness. Once per turn, you can deal an extra 1d8 damage to one creature within 30 feet that you hit with a weapon attack if you have advantage on the attack roll or if that creature is frightened of you.

The extra damage increases by 1d8 when you gain certain levels in this class: at 7th level (2d8), 10th level (3d8), 15th level (4d8), and 18th level (5d8).

Grim Visage

Starting at 7th level, you may use your bonus action to force each creature of your choice within 15 feet of you to make a Wisdom saving throw against a DC of 8 + your proficiency bonus + your Strength or Charisma modifier. On a failed save, the creature becomes frightened of you for one minute. A frightened creature repeats the saving throw at the end of each of its turns. On a successful save, the creature is no longer frightened. An enemy is immune to this effect if it cannot see or hear you or if it can't be frightened. Once you have used this ability, you can't use it again until you finish a long rest.

Underhanded Tenacity

It takes determination and grit to get ahead and stay ahead. Starting at 10th level, when you fail an ability check, you may us this feature to reroll the ability check. You must use the result of the new roll. You can use this feature two times. Once you do, you can't do so again until you finish a long rest unless you expend a use of your Indomitable class feature.

If the ability check was made using one of the two proficiencies you chose with your Underworld Training feature, rather than rolling a new die, you may treat the result of the new roll as a 15 before adding modifiers.

Exploit Weakness

Starting at 15th level, you have mastered the debilitating strike. When you hit with your Dirty Fighting feature, you can force the target to make a Constitution saving throw against a DC of 8 + your proficiency bonus + your Strength or Dexterity modifier. On a failed save, the target is Stunned until the beginning of your next turn.

Terrible Reputation

Starting at 18th level, your fearsome reputation proceeds you like winds before a great storm. Whenever you roll initiative, all enemies within 60 feet of you to suffer the effects of your Grim Visage class feature as long as they can see you and you are not surprised or incapacitated.