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.

Original Idea by (I stole all but 1 thing from this guy): u/runtylizard
Artwork by: Denis Pospelov

Street Hardened

At 3rd level, you gain proficiency with the intimidation skill and one tool of your choice, your proficiency bonus is doubled for checks made with either

Additionally, you can use your cunning action to try to intimidate a creature within 5 feet of you. Make an intimidate check contested by the target's insight check. On a success the creature is frightened of you until the start of your next turn.

Enforcer

Also at 3rd level, you gain proficiency with medium armor and 3 martial weapons of your choice. These weapons must not have the heavy or two handed properties. While you are wielding these weapons, they are considered finesse weapons.

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 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. Once per short rest, when you use your bonus action to intimidate a creature, you can choose to also give the creature the stunned until the start of your next turn. You can choose to do so after you roll, but before you know the outcome. 

Starting at 15th level, 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 make an attack 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 you forgo, you can make one additional attack as apart of the attack action.

Intimidating Aura

At 17th level, your hardened person can scare creatures even if they aren't engaged directly with you. Whenever a creature within 30 feet of you moves toward your general direction, you can use your reaction to try and intimidate the creature. Make an Intimidation check contested by the target's Insight check. On a success the creature is frightened of you until the start of your next turn.