Pugilist

For many fighters, extensive training and rigorous structure is the key to their martial prowess. However, some may find their skills earned through the gritty, difficult process of pain and experience. For those, the most powerful tool in their arsenal is the ability to improvise. In the hands of a Pugilist, creativity is their best weapon - next to the broken leg of a chair, recently emptied bottle of whiskey, or even nothing at all.

The Pugilist makes their mark on the battlefield with the creative use of blunt force. By maneuvering their opponents exactly where they want them, the Pugilist gains the upper hand - literally - by taking the fight with their fingers. By throwing heavy blows and using anything they pick up as a weapon, these fighters can be the most effective when their foes might underestimate them.

Unlike the Monk disciplines, the Pugilist forgoes the traditions and the studies of Ki. The Pugilist understands the proper way to throw a punch, using their strength to their benefit in grappling enemies, and setting themselves up for devastatingly powerful strikes in the process. By using their physique and even their armor to their benefit, a Pugilist should never be underestimated.

Improvised Fighting

At 3rd Level...

Improvised Fighter. Your unarmed strikes now have a 1d6 damage die and can be considered light and finesse weapons. Additionally, at the discretion of your DM, any object that is not a weapon that you collect from your environment and can be wielded in one or two hands can be used as an impromptu weapon. It is up to your DM what weapon is closest to the object you have collected, for example, a broken bottle might be a dagger, a bar stool might be a greatclub, etc. If an object you are using was never intended to be a weapon, it is likely that it will be fragile and could break upon striking an enemy. You may be able to use the broken object as a smaller weapon. Consult your DM for possibilities.

Jab. Whenever you make an unarmed attack using an attack action, once per your turn, you may immediately make an additional unarmed attack as a free action. If this attack is successful, it always deals minimum damage.

Set-up and Pay-off. You know how to make the most of your grapples. If you grapple a target using one of your attacks during your turn and you do not use any movement after grappling it, and that target remains grappled by you at the beginning of your next turn, your first successful attack on each turn against that target has Advantage, and the damage dealt by that successful attack is doubled, so long as the target remains grappled by you.

Practical Brawler

At 7th Level...

Armored Fighting. While wearing medium or heavy armor, your unarmed strikes now deal 1d8 damage, and are considered magical for the purposes of defeating resistances. Additionally, when you use an improvised weapon or object for an attack, it is considered a +1 magical weapon, until it breaks or is discarded.

Haymakers. When making an unarmed strike, you may choose to a take a penalty of -5 to your attack roll to add 10 to the damage dealt by that attack. A Jab cannot receive the Haymaker penalty or bonus damage.

Martial Combination. If at least one of your hands are empty, you can now make an additional Unarmed or Improvised Fighting attack as a bonus action.

Streetwise

At 10th Level...

Opportunist. You have advantage on rolls made to disarm an opponent who is within 5 feet of you. When you successfully disarm an opponent and use your free action to 'Interact with an object' to collect their disarmed weapon, you may make an attack using that collected weapon or object immediately.

Unburdened by Such Things. If all of your hands are empty and you must make a Strength, Dexterity or Constitution Saving Throw, you may choose to reroll that saving throw before learning the result, as a reaction.

A Veteran's Talents

At 15th Level...

Monkey Fingers. Whenever you attempt to grapple a target, that target has disadvantage on their Athletics or Acrobatics checks to contest you.

A Veteran's Guard. On your turn, you may spend your bonus action to defend yourself, increasing your AC by your Strength modifier.

Balanced Stance. You have improved your Haymakers, decreasing the penalty to your attack rolls. You now have a penalty of -2 to your attack rolls instead of a -5, adding 10 damage to the total of your unarmed attacks. Additionally, your Jabs can now receive the Haymaker penalty and damage bonus.

Improved Martial Combination

At 18th Level...

Expert Combo. You can now Jab after any melee attack. If both of your hands are occupied with a weapon, your Jabs are made at disadvantage, and are still unarmed strikes.