Bootlegger (5e Class)

## **The Bootlegger**

**Note: This is inspired by the League of Legends champion, Gangplank.**

The explosive sounds of gunpowder, the clash of steel on steel, and the juicy taste of fresh fruit. These are on average what a Bootlegger will hear and feel, from day to day. Wherever they are called pirates, buccaneers, privateers, or even just members of the navy, a Bootlegger is a force of the seven seas, eager to hack, slash, shoot, and loot.

## **Playing a Bootlegger**

Bootleggers are not a class to be taken lightly. They must get in the fray, constantly, either thriving in the heat of the moment, or being forced to retreat. Their usage of both blades and firearms makes them a powerful threat on either the seas, or the ground.

## **Creating a Bootlegger**

### **Requirements**

**Alignment:** Any

**Starting Age:** Moderate

**Race:** Any

### **Class Features**

As a Bootlegger you gain the following class features.

Hit Points
**Hit Dice:** 1d8 per Bootlegger level

**Hit Points at 1st Level:** 8 + Constitution modifier

**Hit Points at Higher Levels:** 1d8 (or 5) + Constitution modifier per Bootlegger level after 1st

Proficiencies
**Armor:** Light Armor

**Weapons:** Simple and Martial Weapons, Firearms

**Tools:** One Gaming Set or Musical Instrument

**Saving Throws:** Dexterity, Charisma

**Skills:** Choose 2 from Acrobatics, Athletics, Intimidation, Performance, Persuasion.

Equipment
You start with the following equipment, in addition to the equipment granted by your background:

* (*a*) Shortsword & Revolver or (*b*) Shotgun
* (*a*) a Gaming Set or (*b*) a Musical Instrument
* Studded Leather
* 3d6 (10) gold pieces

### **Spells and Whatnot**

#### **Fighting Style**

You adopt a particular style of fighting as your specialty. Choose one of the following options. You can’t take a Fighting Style option more than once, even if you later get to choose again.

##### Archery

You gain a +2 bonus to attack rolls you make with ranged weapons

##### Defense

While you are wearing armor, you gain a +1 bonus to AC

##### Dueling

When you are wielding a melee weapon in one hand and no other weapons, you gain a +2 bonus to damage rolls with that weapon.

##### Great Weapon Fighting

When you roll a 1 or 2 on a damage die for an attack you make with a melee weapon that you are wielding with two hands, you can reroll the die and must use the new roll, even if the new roll is a 1 or a 2. The weapon must have the two-handed or versatile property for you to gain this benefit.

##### Two-Weapon Fighting

When you engage in two-weapon fighting, you can add your ability modifier.

#### **Parley**

Beginning at 2nd level, you can make one weapon attack as a bonus action, adding 1d(2x prof bonus) more damage to the attack. (e.g. greatsword at 2nd level would be 2d6 + str + 1d4) If you have a weapon sheathed, such as a revolver, you can pull it out as part of this attack, even if you are wielding a two-handed weapon (though you must sheath it after making the Parley).

#### **Skill of Choice**

Beginning at 3rd level, you can choose a feature from the list at the bottom of this page. At 9th and 17th levels, you may choose another.

#### **Dubloons**

Beginning at 3rd level, you gain 2 Dubloons, which are magical coins that you can spend as a ritual, taking 15 minutes per Dubloon, to level up your Skills of Choice, up to 5th level. You get 2 of them each 3 levels.

#### **Ability Score Increase**

When you reach 4th level, and again at 8th, 12th, 16th and 19th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

#### **Cannonfire**

At 5th level, you gain the ability to mark a 20 ft. sphere centered on a point, once per long rest. For 3 rounds, at initiative of 20, targets in the area of the sphere must make a DC (10 + your Charisma modifier + your Proficiency bonus) Dexterity check, or take 1d6 + your Charisma modifier piercing damage. At 10th level, the damage is increased to 1d8. At 15th level, the damage is increased to 1d10. At 18th level, the damage is increased to 1d12.

#### **Extra Attack**

Starting at 7th level you gain an extra attack.

#### **Upgraded Cannonfire**

Starting at 10th level, you get to choose one of the following upgrades for Cannonfire. At 15th and 18th levels, you get to choose another. These do not cost any Dubloons. Additionally, you may choose up to four targets that are unaffected by the ability.

##### **Blast Them To Pieces!**

The cannons fire far longer, with this upgrade. Upgrades the round timer for Cannonfire from 3 rounds to 5 rounds.

##### **Bring the Big Guns!**

The cannon fires one large round before the barrage, to destroy who you designate. Choose a point in the range of Cannonfire. Whichever target is on that point must succeed in a DC (12 + your Charisma mod + your Proficiency bonus) Dexterity check, taking 3d12 fire damage on a failure, or half on a success.

##### **Spread 'Em Out!**

The cannons fire in a larger range, to hit more targets. The range of Cannonfire increases from 20 ft. to up to 35 ft., with you choosing how much larger you want it to go.

#### **First Mate**

At 11th level, you may choose a target to be considered your First Mate. Doing so gives them +1 to all attack and damage rolls, and +1 to any ability checks and saving throws you have proficiency in. You can choose to target yourself, receiving the same bonus. It takes 1 hour to change who your First Mate is.

#### **Scurvy Purge**

Starting at 13th level, due to your natural pirate resistance to scurvy and all things disease, you are now immune to diseases.

#### **Swashbuckling**

At 20th level, your fighting prowess has improved dramatically. Once per long rest, you may have two actions in a turn, plus a second bonus action.

## Skills of Choice

Below are the following features you may choose whenever you gain a Skill of Choice feature. You can only upgrade a Skill of Choice to 5th level.

### **Healing Citrus**

Healing Citrus may be used 1 + your Charisma modifier times per long rest (min 1), and using it makes you pull out a citrus (typically an orange but it may be something else, even something that isn't fruit) and eat it, healing 1d6 + your Charisma modifier hit points, and can only be used on yourself. Every Dubloon you spend upgrading Healing Citrus increases the amount of d6s in the healing.

### **Burning Cutlass**

Burning Cutlass may be used 1 + your Dexterity modifier times per long rest (min 1), and using it makes you light your weapon on fire (only applies to melee weapons). The next target you successfully hit with your melee weapon in the next one minute takes an additional 1d4 fire damage, and your speed for the next round is increased by 10 ft. Every Dubloon you spend upgrading Burning Cutlass moves the die size up by 1 for the fire damage.

### **Crew Tactics**

Crew Tactics may be used 1 + your Charisma modifier times per long rest (min 1), and using it makes you command all allies that are within 10 ft. of a hostile target you designate (including yourself if you are in range) to all strike the target. Each strike deals 1d4 + 1/2 their Proficiency bonus damage, and the attack rolls are the same as unarmed strikes, using your Charisma modifier instead of their Strength/Dex modifier. Every Dubloon you spend upgrading Crew Tactics moves the die size up by 1 for the strike damage roll.

### **Raise Morale**

Raise Morale may be used once per long rest, and using it makes you increase the morale of up to five targets + yourself within 30 ft. of you, increasing their movement speed by 10 ft. For every Dubloon you spend upgrading Raise Morale the amount of usages increases per long rest and the movement speed bonus is upgraded by 5 ft.