Picaroon

Those who chose  the lifestyle of the archetypal Picaroon employ fighting tactics that were learned through pirating on the high seas, and the constant desire to survive. A Picaroon might be seen as a dishonorable  fighter, as they will do all that they can to win, including the use of subversive tactics, slick-wit, and pure skullduggery. Not all Picaroons are dishonorable people, but the ones that are willing to get their hands dirty, tend to be the most successful.

Dirty Fighter

When you choose this archetype at 3rd level, you learn maneuvers that are fueled by Maneuver Points.

Maneuvers. You learn three maneuvers of your choice, which are detailed under “Maneuvers” below. You may spend your Maneuver Points to try and perform different dirty Maneuvers in combat. Many maneuvers enhance an attack in some way. You can use only one maneuver per attack.

You learn two additional maneuvers of your choice at 7th, 10th, and 15th level. Each time you learn new maneuvers, you can also replace one maneuver you know with a different one.

Maneuver Points. At the beginning of combat you start with an amount of Maneuver Points = 2 + Your Charisma Modifier(Minimum 2). A Maneuver Point is expended when you use it. You can also gain one additional Maneuver Point on a successful melee attack. You can gain up to a maximum of  2 maneuver points per round through this method.  After combat ends, your maneuver points reset to their base amount.

You gain another base Maneuver Point at 7th level (3 + Your Charisma Modifier) and one more at 15th level (4 + Your Charisma Modifier).

Saving Throws. 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).

Goading Strike (1 Maneuver Point)

When you hit a creature with a weapon attack, you can expend one Maneuver Point to attempt to goad the target into attacking you. You add the superiority die to the attack’s damage roll, and the target must make a Wisdom saving throw. On a failed save, the target can't make attack rolls against targets other than you until the end of your next turn.

"Look Over There!" (2 Maneuver Points)

You may spend 2 Maneuver Points to attempt to distract a target you are attacking. The target must make an intelligence saving throw. On a failed save, their AC is reduced by 1d6 until the end of your turn.

Abiding Strike (3 Maneuver Points)

Carefully gauging the fight at hand, you think you see an additional opening in your opponent's defenses. You may expend 3 Maneuver Points to make one additional attack. This attack does not generate any Maneuver Points.

Bait and Switch (1 Maneuver Point)

When you’re within 5 feet of a creature on your turn, you can expend one maneuver point and switch places with that creature, provided you spend at least 5 feet of movement and the creature is willing and isn’t incapacitated. This movement doesn’t provoke opportunity attacks.

Boot (2 Maneuver Points)

You may spend 2 Maneuver Points to attempt to give your opponent the old boot. Your opponent must make a DEX saving throw. On a failed save, your opponent takes d4 bludgeoning damage and is knocked back 10 feet straight backwards. Movement caused by this maneuver does not provoke opportunity attacks.

Burst of Energy (3 Maneuver Points)

You may spend 3 Maneuver Points to use a free action to dash. On your next turn, you may not use the dash action, and your speed is reduced by half.

Dirt in the Eyes (1 Maneuver Point)

You may spend 1 Maneuver Point to attempt to blind your enemy by throwing dirt in their eyes. Your opponent must make a DEX saving throw. On a failed save, your opponent has disadvantage on their next attack. If your opponent doesn't require their eyes to see, they are immune to Dirt in the Eyes.

Disarming Strike (2 Maneuver Points)

When you hit a creature with a weapon attack, you may expend 2 Maneuver Points to attempt to disarm the target. The target must make a strength saving throw. On a failed save, you knock the object you chose 10 feet away in a direction you choose

Drunken Resilience (2-3 Maneuver Points)

You've probably consumed some alcohol sometime before this fight, and you feel the effects kicking in. When you choose to use this maneuver, you may spend 2 or 3 Maneuver Points. If you spend 2 points, resist d4 damage from each attack made against you until the start of your next turn. If you spend 3 points, resist d4 + your proficiency modifier damage.

Family Jewels (3 Maneuver Points)

You attempt to go straight for the nether regions. Your opponent must make a CON saving throw. The DC they must beat is equal to (8 + your proficiency modifier + your dexterity modifier). On a failed save, the opponent is stunned until beginning of your next turn.

Grappling Strike (1 Maneuver Point)

Immediately after you hit a creature with a melee attack on your turn, you can expend one maneuver point and then try to grapple the target as a bonus action (see the Player’s Handbook for rules on grappling). Add 1d6 to your Strength (Athletics) check.

Jump the Gun (1 Maneuver Point)

When you make your initiative roll, you can expend one maneuver point to add 1d6 to that roll.

Leaping Strike (2 Maneuver Points)

You may spend 2 Maneuver Points and 10 feet of movement. Doing so allows you to increase your attack range by 5 feet until the end of your turn.

Lucky Strike (1 Maneuver Point )

After a successful attack roll, but before damage is rolled, you may choose to spend 1 Maneuver Point to perform a Lucky Strike. If you do, roll a d4. If the result is 2-4, your attack deals maximum weapon damage. If your result is a 1, you miss the attack entirely.

Quick Toss (1 Maneuver Point)

As a bonus action, you can expend one Maneuver Point and make a ranged attack with a weapon that has the thrown property. You can draw the weapon as part of making this attack. If you hit, add the 1d6 to the weapon’s damage roll.

Savage Words (2 Maneuver Points)

You may expend 2 Maneuver Points to lob a slurry of vicious taunts and insults at an opponent you can see. They must make  a wisdom saving throw. On a failed save, they have disadvantage on attack rolls until the end of their next turn.

Sweep the Legs (1 Maneuver point)

When you hit a creature with a weapon attack, you can expend one maneuver point to attempt to knock the target down. You add the superiority die to the attack’s damage roll, and if the target is Large or smaller, it must make a Strength saving throw. On a failed save, you knock the target prone.

Fearsome Swashbuckler

At 7th level, you gain the dual wielder feat. See Players Handbook (Page 165) For more information on the feat.

Dirtiest Fighter

At 10th Level, you’re Unarmed Strike to hit = your proficiency + your strength or dexterity. Unarmed Strike Damage rolls become 1d4 + your proficiency modifier + your Strength or Dexterity Modifier

 

You can choose to spend 1 maneuver point and use your bonus action to make an unarmed strike.

Pirate Legend

Starting at 15th level, you’re Unarmed Strike to hit = your proficiency + your strength or dexterity. Unarmed Strike Damage rolls become 1d8 + your proficiency modifier + your Strength or Dexterity Modifier.

You can choose to spend 2 maneuver points and use your bonus action to make two unarmed strikes.

Lord of the Pirates

At 18th level, you can use your reaction to perform a maneuver.