A shadow-themed, battlemaster-like Monk subclass centered around grappling. A master of battlefield control and mobility in the dark. Manipulate the shadows to quickly ambush enemies while utilizing finesse based grappling techniques incorporated into your strikes. Follow up with specialized martial maneuvers as you manhandle opponents into submission.

Grappler's Conditioning

Gain proficiency in either Strength (Athletics) or Dexterity (Acrobatics). If you already have proficiency in the chosen skill, gain expertise in it instead.

Shadow Grasp

At 3rd level you have honed specialized grappling techniques that allow you to grapple effectively using joint manipulation and body weight distribution to your advantage.

• When you hit a creature with an unarmed strike or monk weapon on your turn, you can use a bonus action to attempt to grapple the target provided you have at least one hand free.
• You may use Athletics (Strength) or Acrobatics (Dexterity) when attempting a grapple check.
•  You count as one size larger when determining or maintaining a grapple check. On a check to initiate a grapple, you may increase the effective creature size that you can grapple by spending 1 ki point per size category.

Shadow Grasp Maneuvers

When you choose this archetype at 3rd level, you learn how to exploit a grappled foe to your advantage. In place of one of your strikes during an attack, you may choose to perform one of the following maneuvers instead on a opponent with whom you are grappling. You learn three maneuvers of your choice, which are listed below.  You can use only one maneuver per attack. Some maneuvers can only be learned at higher levels. You may only learn a maneuver for which you meet the required class level. You learn two additional maneuvers of your choice at 6th, 11th, and 17th level. Each time you learn new maneuvers, you can also replace one maneuver you know with a different one.

Some of your Maneuvers require your target to make a saving throw to resist the maneuver's effects. The saving throw DC is calculated as follows:

Maneuver save DC = 8 + your proficiency bonus + your Strength or Dexterity modifier (your choice)

Break (3rd level)

Manipulate the body of your opponent in a way it's not supposed to go. Attempt a Grapple check against a grappled opponent. On a success deal damage to them equal to your unarmed strike and your opponent has disadvantage on their next attack roll. On a failure your opponent may use their reaction to make an attack of opportunity against you.

Improvised Maul (6th level)

Use your grappled opponent as an improvised weapon against an adjacent target. Attempt a Grapple check against a grappled opponent. On a success, without losing the Grapple condition, you build up enough momentum to whip your grappled opponent into an adjacent target. Both targets take damage equal to your unarmed strike. On a failure your opponent may immediately use their reaction to try and escape the grapple.

Nethercloak (6th level)

Siphon off your opponent's shadow to provide yourself with additional protection. Attempt a Grapple check against a grappled opponent. On a success your opponent's shadow forms a barrier around you providing temporary hitpoints equal to your monk level plus your proficiency bonus. If you succeed, you cannot reuse this ability for 1d4-1 rounds. On a failure your opponent may use their reaction to make an attack of opportunity against you.

Night Mask (11th level)

Shadows stretch outwards from your form, coiling around your opponent's body and covering their face, effectively blinding them. Attempt a Grapple check against a grappled opponent. On a success your opponent's eyes are wreathed in shadow as they gain the Blinded condition until the start of your next turn. If the opponent can see through magical darkness or does not use vision as their primary means of navigation, this technique has no effect. On a failure your opponent may use their reaction to make an attack of opportunity against you.

Night Terror (11th level)

Shadows warp your appearance into the stuff of your enemies nightmares. Your opponent must make a Wisdom saving throw against your maneuver DC as shadows warp your visage. On a failed save, they are frightened of you until the end of your next turn. On a successful save, they are immune to this ability for 3 rounds.

Pin (3rd level)

You may attempt to restrain the opponent by pinning them either through bodily manipulation or against a solid surface. Attempt a Grapple check against a grappled opponent. On a success both you and your opponent are Restrained until the start of your next turn. You may end this condition at anytime before then start of your next turn if you choose to do so.

Shadow Bind (3rd level)

You command the shadows around you to coil around your opponent restricting their movements and bolstering your grasp upon them. Your opponent has disadvantage on the next contested Grapple check they make against you. This benefit lasts until the start of your next turn.

Shadow Reversal (6th level)

Wreath your opponent in shadow, priming them to instantly manipulate your positions when threatened. Attempt a Grapple check against a grappled opponent. On a success until the start of your next turn, you can impose disadvantage on one attack roll made against you by another entity as you maneuver your grappled opponent into the path of the attack. If an attack against you misses, you may spend 1 ki point and use your reaction to exchange places with your grappled opponent forcing them into the attack.The attacker must make a new roll using the same attack against your grappled opponent. On a failure your opponent may use their reaction to make an attack of opportunity against you.

Toppling Retreat (3rd level)

Throw your opponent to the ground as you move away. Attempt a Grapple check against a grappled opponent. On a success, knock your opponent prone as you break the grapple, dealing damage to them equal to your unarmed strike and you can move up to half your speed. During this movement, your opponent cannot use their reaction to make an Attack of Opportunity against you. This does not apply to other enemies in the vicinity.  On a failure, you do not break the Grapple, your opponent takes no damage, is not knocked prone, and your opponent can use their reaction to make an Attack of Opportunity against you.

Twilight Exchange (17th level)

Siphon off the shadow of your opponent to staunch your wounds and restore your own vitality. Attempt a Grapple check against a grappled opponent. If you succeed, restore hitpoints equal to your class level plus your proficiency bonus. On a success you cannot reuse this ability for 1d4-2 rounds.

Twilight Pocket (3rd level)

Siphon away your opponent's shadow creating a pocket of twilight. Attempt a Grapple check against a grappled opponent. On a success your opponent's shadow transforms into an aura of dim light with a 15 foot radius.  This aura is centered on your opponent's current location, does not move and lasts for 3 rounds.

Voiceless Void (17th level)

Your opponent's shadow flows upwards, tightening around them and filling their mouth. Attempt a Grapple check against a grappled opponent. On a success your opponent takes bludgeoning damage equal to your unarmed strike and they are Silenced until the start of your next turn. On a failure nothing happens.

Wresting Shadow (11th level)

Attempt to disarm your grappled opponent. Attempt a Grapple check against a grappled opponent. On a success you disarm the target, forcing it to drop one item of your choice that it's holding. The object lands at its feet. As part of this maneuver, you may spend 1 ki point to instantly pick up the object provided you have one hand free aside from your grappling hand. On a failure your opponent may use their reaction to make an attack of opportunity against you.

Shadow Step

At 6th level, you gain the ability to step from one shadow into another. When you are in dim light or darkness, as a bonus action you can teleport up to 60 feet to an unoccupied space you can see that is also in dim light or darkness. You then have advantage on the first melee attack you make before the end of the turn.

Nightfall

At 6th level, you're able to drag or throw an opponent across the battlefield in an instant, slamming them into the ground for a devastaing blow. In place of one of your strikes during an attack,  when you are in dim light or darkness, you may instead attempt a Grapple check against a grappled opponent. If you succeed, you may either:

a) Teleport up to 30 feet to a point you can see that is also in dim light or darkness, dragging the opponent with you.

b) Fling your opponent into the darkness around you, exiting from any point you can see within 30 feet that is also in dim light or darkness.

Your opponent (or you and your opponent) are ejected with great force, landing at a point of your choosing within 30 feet of the exit portal. Use the momentum to slam the opponent down for 6d6 bludgeoning damage, knocking them prone. If you traveled with the opponent, you land safely in the nearest square of your choice next to them. Any other creatures impacted by your opponent must make a Dexterity saving throw against your maneuver DC. A target takes 6d6 bludgeoning damage and is knocked prone on a failed save, or half as much damage and remains standing on a successful save. An aura of dim light expands from the point of impact in a 15 foot radius and lasts for 3 rounds.

Once used successfully, it cannot be used again for 1d4-1 rounds.

Twilight Dance

At 11th level you can make a furious assault upon nearby enemies using a grappled opponent as your weapon. As an action, make a Grapple check against a grappled opponent. On a success, an aura of dim light filled with tendrils of shadow emanates from you in a 30 foot radius lasting until the end of your next turn and is considered difficult terrain for enemies.

Choose up to five creatures you can see within the 30 foot radius. Rapidly teleport among the targets while using your grappled opponent as a weapon, make an unarmed strike against each target. Your grappled opponent takes half of the damage dealt to each target. At the end of the assault, position yourself and your grappled opponent adjacent to any one of the targeted creatures. Once successfully used, this ability may not be used again for 1d4 rounds.

The Long Night

At 17th level, as a bonus action you emanate an aura of dim light extending outwards in a 30 foot radius moving with you and lasting for 3 rounds. While the aura is active, shadows envelop your form enhancing your abilities. During this time,  your melee strikes deal an extra 1d8 cold damage and enemies have disadvantage on attacks against you. Additionally you may teleport up to 60 feet to any location in dim light or darkness immediately before making a melee attack.

Enemies who move into or start their turn within the magical darkness must make succeed on a Constitution saving throw against your class DC or be grappled by the shadows. The DC to break free is equal to your class DC. The first time an enemy enters the area on their turn or starts their turn within the radius, they take 2d8 cold damage. The area counts as difficult terrain for enemies. You can use the aura a number of times equal to your proficiency bonus and all uses are refreshed after a long rest.