Brutish Scoundrel v2
Usually found in a back alley, punching money out of a rich bypasser, the brutish scoundrel is a rogue that normally doesn't operate sneakily. These kind of rogues are often hired by syndicates to put some fear back into loaners and grifters. Contrary to other thievish colleagues, they mostly rely on their brute strength and intimidating appearance.
Street-Hardened
At 3rd level, you gain proficiency in the intimidation skill. Your proficiency bonus is doubled for any check you make with this proficiency.
Additionally, you can use your cunning action to try to intimidate a creature within 5 feet of you. The target must succeed on a Wisdom saving throw against your Intimidation Save DC or be frightened of you until the start of your next turn.
Intimidation Save DC
Enforcer
Also at 3rd level, you gain proficiency with medium armor and some weapons of your choice. Choose three simple or martial weapons that lack the heavy, or two handed property. You gain proficiency in them if you don't already have it and if a chosen weapon is a melee weapon, it gains the finesse property while you are wielding it.
You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it and the creature is frightened of you.
Stunning Stare
Beginning at 9th level, you bring creatures to a complete halt with your intimidating presence. When you successfully intimidate a creature, you can choose to also stun the creature until the start of your next turn. You can use this feature once per short or long rest.
Starting at level 15, you can use this feature twice between rests.
Brutish Flurry
Starting at 13th level, you can choose to hit less hard and instead more often. Whenever you take the attack action and qualify for Sneak Attack, you can choose to forgo a number of d6s to make additional attacks. For every 3d6 of your Sneak Attack damage you forgo, you can make one additional attack as part of the attack action. Alternatively, you can use one of these attacks on your turn to grapple a creature.
Control through Fear
At 17th level, your hardened persona can scare creatures even if they aren't directly engaged with you. Whenever a creature you can see within 30 feet moves in your direction, you can use your reaction to try and intimidate the creature. The target must succeed on a Wisdom saving throw against your Intimidation Save DC or be frightened of you until the start of your next turn.
Orc Brawler
Watercolor Stains by Jared Ondricek