Prerequisites: Sailor Background, Tavern Brawler feat before level 15

The true swashbuckler uses all sorts of dirty fighting and cheap tactics to win in any fight (not any fight) (very limited pool of fights he can win), he'll use his intimidation he has gotten over the years of pirating to ward of the most deadly foes (merchants), and swindle his way to the greatest treasures (1 silver off of the inn for a night), the true swashbuckler is really only good for one thing, pissing off your enemies, and probably allies too (if you have any), the TS excels in one on one combat, with stalling until you finally kill your target or makin git so they don't want to fight you anymore. 

Level 3: Dirty Fighting

At level 3 during your years of pirating, you have used many different ways of fighting dirty and are now proficient in three ways.

Dirt Slinging- as a bonus action, you can throw dirt, sand, dust, etc. at a target within 5 ft of you and cause the target to make a DEX saving throw to avoid the pocket particles, the target must make a DEX saving throw with a save DC of 16 and on a failure the user can choose to either impose disadvantage on the targets next attack or the first attack on the target has advantage, on a Success nothing happens.

Dirty Grappling- when you grapple somebody, on that turn you can make 1 unarmed strike as if it were a regular attack. When you gain extra attack at level 5 you can make more unarmed strikes the first turn equal to the number of extra attacks you have. And on any turn past the first when you let go of the grappled target either through you releasing them or, them prying themselves free you can make 1 free extra unarmed strike on the target. For all unarmed strikes made with this feature, the damage is only the dice roll's amount no modifiers.

Reckless Charge- on an action you can charge 15 ft forward on to an enemy to bring both you and them down, you make an attack roll with STR and prof modifiers and if you make their AC both you and the target fall prone, you then must make a 14 STR save, and on a fail your movement falls to 0, and you stay prone that turn, on a success you just fall prone. You can still use your bonus action even if you fail. If you miss the attack you instead just fall prone next to them but your movement is not 0 just 15 less than your regular movement. This also deals your unarmed strike damage + STR mod an Prof bonus.

Level 7: Pirating Experience

At level seven, through your years you have gained the ability to make people fear you as you walk through town, and swindle your way to treasure, you gain expertise in Intimidation, and Persuasion, even if you don't have proficiency in these skills.

Level 10: Increased Dirty Tactics

At level 10, after your repeated use of your Dirty Fighting techniques you have thought of three more tactics to increase your odds of beating your opponent after making them increasingly angry. 

Pirate's HighGround- on a bonus action you can make an attack roll to trip your opponent, make an attack roll with STR and Prof modifiers if you make their ACs the target falls prone.

Pirate's Low Ground- When you are prone, due to your great will to live, or your fear of pain, you roll on the ground attempting to avoid oncoming attacks, all attacks have disadvantage on hitting you and if you are being targeted by a spell that makes you roll a DEX save you roll flat. (Idk if the spell part changes anything, but idc)

Cheap Shot- When you are targeting someone who is prone with a melee attack within 5 ft, your critical hit range is 15-20 only when you are not prone, and they are prone (because you are prone a lot with this sub class)

 

 

 

Level 15: Pirate Brawler

At level 15, through your continued years of cheap shots and under the belt strikes, your tavern brawler features have been increased, instead of 1d4 your unarmed strikes do 1d6 and if you have the unarmed fighting style you can change the dice to always be a d8. And the reroll feature changes to a 1 or a 2 and you can take a 2 if you roll a 1 for the second roll. (For clarification you still can't make a bonus action attack with the unarmed strike but the features that allow you to make unarmed strikes on top of your regular attacks in the subclass benefit from this most unless you are fighting unarmed.)

Level 18: "Perfect" Dirty Fighting

At 18th level, you have made your dirty fighting perfect, at least as perfect as it can be, your original 3 dirty fighting techniques have been upgraded.

"Perfect" Dirt Slinging-  The DC for the Dirt Slinging is instead now 18 and the disadvantage and advantage last until the end of the targets next turn and all attacks made against it have advantage on it for that time and all saves involving DEX and all attacks it makes have disadvantage, and if it is holding concentration on a spell it must make a DC 16 concentration saving throw or lose concentration on that spell.

"Perfect"  Dirty Grappling- When making the initial grappling check you have advantage on the check and every sequential check to get out of the grapple, the target has disadvantage. And now not just on the first turn you can make 2 unarmed strikes on the target you have grappled with advantage with STR and Prof modifier to hit(only these two attacks have advantage) On the first turn the amount of attacks you can make are the same. And the damage for these unarmed strikes is only the dice amount +1.

"Perfect" Reckless Charge- The save you have to make is reduced to only a 12 STR DC and the target if it is a hit is now stunned as well as prone. And now if you miss the attack you don't fall prone. The stunned condition lasts until the end of their next turn. You also don't get stunned if you fail the saving throw you still do fall prone