Ruffian

As tempting as the prospect of wealth and power might be, there will always be those who seek to take it from you. Influential people therefore often employ bodyguards to ensure their protection. These ruffians do not follow military procedures other guards might hold sacred. For them, there is only one goal: to protect those they have either sworn to or are being paid to protect. To do so, they are not afraid of playing dirty. After all, honor does not pay for anything if the source of the payment died for it.

You will give your life to shield others from harm. When a creature within 5 feet of you is hit by an Attack Roll, you can expend a use of your Grit Damage Reduction feature to reduce the damage dealt to them. If the target still takes damage, you gain a Grit Point as if you had been hit by the attack.

The shield you carry can be both a defensive and an offensive tool. While carrying a Shield you can use your Bonus Action to attempt the Shove option of the Unarmed Strike rule with it to push a creature away or knock it Prone.

You can use this feature without a Shield; in this case the target has Advantage on its Saving Throw against the Shove.

You know how to get your allies out of harm's way. Once on your turn you can expend half your Movement Speed to touch a willing creature and swap places with them. The target can immediately move up to half their Speed without provoking Opportunity Attacks.

You can use this feature a number of times equal to your half your Charisma modifier (rounded up, minimum of once). You regain one use of this feature when you finish a Short Rest and all of its uses when you finish a Long Rest.

You can shield a creature from harm. As a Bonus Action on your turn, you can expend four Grit Points to touch a creature. As long as the target remains within 5 feet of you, you grant it Three-Quarters Cover until the start of your next turn.

You can draw attention away from those you have sworn to protect, but doing so leaves yourself open to attacks. At the end of your turn, all creatures of your choice within 30 feet of you that are fixated on you make a Intelligence Saving Throw against your Daunting Presence Save DC.

On a failed save, the creature must use its Action on its next turn to try dealing damage to you. Any Attack Rolls they make against you gain Advantage and you have Disadvantage on all Saving Throws against them.

You are willing to sacrifice yourself for those you have sworn to protect. When a creature within 30 feet of you is reduced to 0 Hit Points, you can use your Reaction to rush to their side. You can move up to your speed towards the target. If you make it within 5 feet of the target, they regain Hit Points equal to your current Grit Points times 10. You then lose the same amount of Hit Points.

If this features causes you to drop to 0 Hit Points and fall Unconscious, you immediately become stable.

Once you use this feature you cannot use it again until you finish a Long Rest.

While most Ruffians know how to wield a weapon, not all of them prefer doing so. Sometimes a good old right hook can get you places as well. Brawlers are often involved in bar and street fights. There is something honorable about meeting your foe eye to eye to determine the outcome of a fight with no weapons but just the pure strength of your arms. Brawlers are often employed by crime lords to intimidate rivals and to make sure that debts are paid. When the fist of a Brawler hits your jaw and you can hear an unsettling crack, you'll think twice about angering them again.

Your left and right hooks are feared everywhere.

When you aren't wearing Medium or Heavy armor or wielding a Shield, you gain a bonus to your AC equal to your Constitution modifier (minimum of +1).

Immediately after you make an Unarmed Strike, you can spend 2 Grit Points to take the Dodge Action. Until the start of your next turn, you gain a special reaction that you can take on every creature's turn except your turn. You can take this reaction only to make an Opportunity Attack, and you can't take it on the same turn that you take your normal reaction.

Whenever you take the Dodge Action, you can use your Counter feature when you are targeted by an Attack Roll while you are dodging, even if the attack misses or doesn't deal damage.

You hit like a truck. What's a truck? I don't know.

As a Bonus Action, you can force a creature within 60 feet of yourself that can see or hear you into a duel. The target makes an Charisma Saving Throw against your Daunting Presence Save DC. A creature that is fixated on you makes this Saving Throw with Disadvantage. On a failed save you and the target both get Disadvantage on all Attack Rolls against targets other than each other, and every other creature gains Advantage on Saving Throws against your spells and abilities.

The Duel lasts for one minute or until one of you is reduced to 0 Hit Points. If you reduce the target to 0 Hit Points you can choose to expend any available Hit Point Dice and heal for the amount rolled without adding your Constitution modifier.

Your punches can leave a creature reeling. Once on a turn when you hit a creature with an Attack Roll, you can expend two Grit Points to lay extra weight into the punch.

The target makes a Constitution Saving Throw against a DC of 8 + your Proficiency Bonus + the Ability Modifier used for the attack. On a failed save the creature's Movement Speed is halved, it cannot take Reactions and it can only use an Action or a Bonus Action (not both) on its turn until the start of your next turn.

Your punches leave your opponent crippled. Whenever you hit with an Unarmed Strike and deal damage, the target's Movement Speed is reduced by 10 feet until the start of your next turn. This effect can stack.

You know how to get things done, and you don't mind fighting dirty to get there. Life on the street has not only told you how to take a hit, but also how to strike one where it really hurts.

You know how to hit where it hurts, and you don't hesitate to do it. Once per turn, you can deal an extra 1d8 damage to a creature you hit with a melee attack roll if you have Advantage on the roll. The extra damage's type is the same as the weapon's type.

The extra damage increases as you gain Ruffian levels, as shown in the Below the Belt column of the Ruffian Features table.

You are an expert at annoying and distracting your opponents. You can use the Help action as a Bonus Action. Instead of giving an ally Advantage against an opponent within 5 feet of you, you can choose to give the opponent Disadvantage on their next attack against a target other than you before the start of your next turn.

Whenever you use your Barrage feature to gain additional attacks, you can instead use it to empower your Below the Belt feature.

Each Grit Point you spend increases the damage of your Below the Belt feature by 1d8.

You gain Expertise in two of your skill proficiencies of your choice. Athletics and Intimidation are recommended if you have proficiency in them.

You've added a few tricks to your Below the Belt. When you deal Below the Belt damage, you can add one of the following Twist the Knife effects. Each effect has a die cost, which is the number of Below the Belt damage dice you must forgo to add the effect. You remove the die before rolling, and the effect occurs immediately after the attack's damage is dealt. For example, if you add the Grapple effect, remove 1d8 from the Below the Belt's damage before rolling.

You gain proficiency in Wisdom and Charisma Saving Throws.

You cannot be critically hit. If an attacker rolls a 20 on an Attack Roll against you, the attacker rolls the attack's damage dice only once.

Fighting the good (or bad) fight might lead to a lot of kinship. Some Ruffians form tight bonds with their companions, even if it is just the lust or need for money that brings them all together. These Sentrys are hell-bent on making sure that none of their allies get hurt, and their resilience and determination inspires those around them to never give up. Even–or perhaps especially–if the odds are against them.

Your perseverance in the face of pain encourages your allies to fight harder. Whenever you expend Grit Points, you may give Encouragement to a creature other than yourself within 60 feet that can see or hear you. The target gains a bonus equal to half your Charisma modifier (rounded up, minimum of 1) to either their Saving Throws, Armor Class, or Attack Rolls until the end of their next turn. The target chooses one of the effects when you activate this ability.

You can be knocked down 10 times, but stand up 11! When you make a Death Saving Throw, a total result of 19 or better counts as if you had rolled a natural 20.

Additionally, each time you make a Death Saving Throw–prior to rolling–you may expend any number of Grit Points to add this number to the roll.

You hate seeing your friends get hurt. When a creature that you can see or hear is hit by an Attack Roll and takes damage, you can expend 3 Grit Points and your reaction to move up to your speed toward the attacker and use your Counter ability as if you had been the target of the attack.

Allies benefitting from your Inspiring Toughness feature now add your full Charisma modifier instead of half (minimum of 1).

Additionally, they may instead use the bonus to apply it to the save DC of spells or abilities they use or to their Death Saving Throws they make before the end of their next turn.

Whenever you use your Grand Entrance feature you may grant Inspiring Toughness to any number of allies within range of the effect.

Additionally, you may use your Grand Entrance feature again whenever you regain consciousness as the result of a Death Saving Throw.

You can use your Last Stand feature once per Long Rest without expending any Grit Points.

Additionally, when an ally within 60 feet of you that you can see is reduced to 0 Hit Points, you may use your Reaction to let them use your Last Stand feature. The target expends their own Hit Point Dice and adds your Ruffian level to determine the number of Hit Points gained. If they have no Hit Point Dice remaining, they cannot benefit from this feature.