Scoundrel (Entrellia)

Brutish and raised by the hard urban streets, you learned to fight dirty and with force. Taking what you wanted and having no one to answer to, your desires to rob, mug and murderer were second to none and your skills truly showed that. The shadows were only a small part to play in your mean attacks, instead you relied on strength and power to shove people smaller than you into the dirt. You got your way, that's for sure.

Thuggery

Starting at 3rd level, your life amongst the rough streets have taught you hardier, heavier tactics, you gain proficiency with medium armor, shields, and 2 martial weapons of your choice that deal bludgeoning damage. Additionally, you can ignore the finesse requirement and apply your Sneak Attack feature on an attack made with weapons that lack the Two-Handed trait, as long as the other Sneak Attack requirements are met to apply it.

Filthy Brawls

Also at 3rd level, your fearsome behavior has become ingrained in your mind and body, you gain proficiency in the Intimidation skill if you do not already have it and your hit point maximum is increased by 2 per Rogue level, to a maximum of 40 bonus hit points at level 20.

In Addition, you can use your Cunning Action feature as a bonus action to grapple a creature. You can apply your Sneak Attack feature on an attack creatures grappled by you as long as the other Sneak Attack requirements are met to apply it.

At 9th level, you can use your Cunning Action feature as a bonus action to shove a creature.

Hardened Mobster

At 9th level, messy battles are your specialty, whenever you use your Uncanny Dodge an attack or use Evasion to dodge an area effect, until the start of your next turn, you have resistance to the damage type of the attack or effect. This resistance applies after the damage from the initial dodge or evade is calculated.

You also gain advantage against being frightened.

Known Threat

At 13th level, your presence alone installs fear in the foes you fight. When entering combat, before initiative is rolled, creatures of your choice that you can see and are within 30 feet of you each have their initiative roll reduced by your proficiency bonus modifier. Once you apply this feature, you can't use it again until you finish a long rest.

Fatal Finisher

At 17th level, you can finish off your victims while they are most vulnerable. When you hit a creature that is prone, restrained, or grappled by you with a melee attack, you can choose to score a critical hit instead. Once you do so, you can't use this feature again until you finish a short or long rest.