Deceitful and Ingenious, monks who follow the way of The Underdog tend to be disolutioned with most other strict or, in their opinion, outdated monastic traditions and decide to instead carve their own path by use of wit, recklesness and a fair amount of skulduggery. They forgo the study of ki in exchange for improving their reflexes and physical prowess so they may endure attacks from either large groups or single mighty foes while also being able to strike back twice as hard.

To an Underdog, surviving each encounter is its own purpose and reward. They trhive in conflict and unfair fights where they can let loose and become a flurry of punches, kicks and visceral attacks. Those who survive long enough become focused and learn to exploit their enemies’ blunders and moments of weakness to deliver devastating and swift retaliating strikes.

An underdog can come from any cultural or social background but they seem share some common traits: a disgruntled attitude towards figure of power, a foolhardy confidence and the unending drive to improve themselves.

 

*Author's note: please note that due to this being the first ever subclass I homebrew and publish in DnDBeyond, it's bound to be rough around the edges and maybe some features or effects probably won't be coded properly. Please don't be harsh as this was my attempt at making the monks better at being martials focused on dodge-tanking. Thanks for reading and I hope it may bring you fun if you implement it in your games!

Underhanded Training

Starting at 3rd level, you have survived enough scuffles alongside, or against, unsavoury people that some of their skills and roughness have sticked to you. You gain the following benefits:

• Hardened Scars: the beatings you have endured have made you more resilient. Your hit points maximum increases by 3 and increases by 1 again whenever you gain a level in this class.
• Dirty Fighting: whenever you use Flurry of Blows you can choose to make one of the strikes to blind to your target instead of dealing damage (this can be done by throwing pocket sand, poking their eyes, etc) until the beginning of your next turn. This property can’t be used against creatures who are more two or more size categories above you. Additionally, improvised weapons are added to your options for monk weapons.
• Shady Personality: you gain proficiency in Intimidation or Deception. If you already had proficiency in the chosen skill, you instead gain Expertise.

Deception

You gain proficiency in the Deception skill. If you already had proficiency, you instead gain Expertise

Intimidation

You gain proficicency in the Intimidation skill. If you already had proficiency, you instead gain Expertise.

Bob and Weave

At 6th level, you have learnt to dodge like an annoying fly and hit back like a mean wasp.

When a creature misses an attack against you in the same round you took the Dodge action, you regain 1 ki point. Additionally, when a creature misses you with a melee attack, you can use your reaction and expend 1 ki point to make an unarmed or improvised weapon attack against that creature.

 

Punching above your weight

Starting at 6th level, your reckleness has taught you how to wrestle foes with finesse and use them as your own weapons. You gain the following benefits:

• Enemies can’t gain advantage on grappling checks against you, whether from magical or natural effects, and you can drag creatures grappled by you at no additional movement cost.
• You can use your Dexterity bonus instead of your Strength bonus for grappling checks.
• If you end a grapple by succesfully shoving a creature you are grappling, or is grappling you, you push it away horizontally a number of feet equal to your Dexterity score. If the creature collides with an object or another creature, they both take bludgeoning damage equal to a roll of your Martial Arts die.

Against All Odds

Beginning at 11th level, you have become accostumed to uneven fights, whether against large groups, massive enemies or in challenging environments; and use them to your advantage. You gain the following benefits:

• If you are within 5ft of two or more hostile creatures, their attack rolls against you receive a negative modifier equal to the number of hostile creatures within 5ft of you. You also gain a bonus to your attack rolls equal to the number of hostile creatures within 5ft of you.
• Additionally, creatures bigger than you receive a negative modifier to their attack rolls against you equal to as many size categories they are above you. For example, a Large creature who attacks a Medium creature with this feature would have a -1 modifier to their attack rolls, a -2 if they were Huge and so on.
• Lastly, you gain blindsight up to 15ft and, when you use Step of the Wind, difficult terrain doesn’t cost you extra movement to traverse.

Against All Odds

• If you are within 5ft of two or more hostile creatures, their attack rolls against you receive a negative modifier equal to the number of hostile creatures within 5ft of you. You also gain a bonus to your attack rolls equal to the number of hostile creatures within 5ft of you.
• Additionally, creatures bigger than you receive a negative modifier to their attack rolls against you equal to as many size categories they are above you. For example, a Large creature who attacks a Medium creature with this feature would have a -1 modifier to their attack rolls, a -2 if they were Huge and so on.
• Lastly, you gain [Tooltip Not Found] up to 15ft and, when you use Step of the Wind, difficult terrain doesn’t cost you extra movement to traverse.

Foul Wit

At 17th level, you have learnt and honed the most vicious techniques picked from corner to corner of the realms. You gain the following benefits:

• No room to breathe: the number required for you to roll a critical hit is reduced by 1 when you attack a creature affected by at least of the following conditions: blinded, grappled, incapacitated, restrained, prone, frightened.
• No foe too big to topple: you ignore the size restriction for melee attacks from Dirty Fighting.
• In the zone: the number of ki points you gain from Bob and Weave are increased to 2 and, when a creature misses an attack against you, you can spend 2 ki points to make a Flurry of Blows as a reaction (this can target creatures other than the one who triggered your reaction). Additionally, whenever you take the Dodge action you add your Dexterity modifier twice when calculating your Armor Class.