Ruffian

Not all Rogues rely on cunning and subterfuge to thwart their foes. Ruffians prefer to face enemies directly with devastating blows and their ruthless style of combat. Often employed as hired muscle for thieves' guilds, gangs, and other groups that don't shy away from the use of violence, Ruffian Rogues can be found in any settlement or city where crime holds sway.

Ruffian Exploits

3rd-level Rogue (Ruffian) Feature
You learn certain Exploits at the Rogue levels noted in the table below. These don't count against your total number of Exploits Known and can't be switched upon gaining a level.

Rogue Level	Exploit
3rd	streetwise, sweeping strike
5th	dirty hit, grasp of night
9th	recruit informant

Enforcer

3rd-level Rogue (Ruffian) Feature
You use brute force not often employed by Rogues in combat. Your unorthodox fighting style grants you the benefits below:

You gain proficiency with improvised weapons.

Your unarmed strikes deal bludgeoning damage equal to one roll of your Exploit Die + your Strength modifier.

You can apply your Sneak Attack bonus to your attacks with improvised weapons, unarmed strikes, and simple melee weapons. All other Sneak Attack rules still apply.

You can use the bonus action granted by your Cunning Action to attempt a grapple or shove attack.

You can use your Constitution, instead of Dexterity, to calculate your Armor Class in light and medium armor.

Shake Down

3rd-level Rogue (Ruffian) Feature
Your work requires skills that you have become particularly reliable in employing. You gain proficiency in Intimidation, and whenever you make a Strength (Athletics), or a Strength (Intimidation) check, you can treat a roll of 7 or lower on the d20 as an 8.

Intimidating Blow

7th-level Rogue (Ruffian) Feature
Your ruthless style of fighting inspires fear in your enemies. When you hit a creature with a melee attack that adds your Sneak Attack bonus, you can use Cunning Strike to reduce the bonus by 2d6 and force the target of your attack or one creature that can see you within 30 feet to make a Wisdom saving throw against your Exploit save DC. On a failed save, it is Frightened of you until the end of your next turn.

Nerves of Steel

7th-level Rogue (Ruffian) Feature
Fear is a weapon that only works against cowards and the weak-willed. You gain immunity to the frightened condition.
In addition, you have advantage on any weapon attacks you make against a creature that is currently frightened of you.

Criminal Connections

13th-level Rogue (Ruffian) Feature
You have a knack for finding criminal connections in any city. You learn the Clandestine Source Exploit, but it doesn't count against your total number of Exploits Known.

Dodge & Counter

13th-level Rogue (Ruffian) Feature
You can use your enemies' momentum against them. When a creature that is one size larger than you or smaller misses you with a melee attack, you can use your reaction to force it to make a Dexterity saving throw against your Exploit Save DC. On a failed save, it suffers one of the following effects:

It falls prone and its speed is 0 for the rest of that turn.

If you have a free hand, you can automatically grapple it.

You can make one unarmed strike attack against it.

Ruthless Strike

17th-level Rogue (Ruffian) Feature
You strike with at those who fear you with ruthless intent. When you add your Sneak Attack bonus to a melee weapon attack against a creature that is frightened of you, you can choose for your attack to become an automatic critical hit.
Once you use this feature you must finish a short or long rest before you can use it again.