Gangster

An aspiring politician in a bustling city has come in contact and made the use of some unsavory crime bosses. Having recently "won" an election, the politician celebrates in their decoration mansion in the wealthy community of their city. Fellow politicians, celebrities, affluent contributors, friends, and family are all present as they drink and dance their way into the night. However, the politician sits in their room in a cold sweat realizing that they cannot afford the debt created by enlisting the help of the crime bosses for the election. It is at this moment when a well dressed individual enters the room, pours the politician a drink, and sits with them at a table when all of the fears of the politician manifest before them. Enter, the Gangster Rogue, here to collect the debt one way or another. 

The Gangster Rogue thrives in the criminal underworld of any city. Your silver tongue and bombastic firearm are your tools for negotiation between big city crime bosses and petty street thieves. While some rogues wish to plan out a masterful heist taking weeks to fully scope out from the shadows, the Gangster focuses on pulling strings, cashing in favors, and striking fear into those who can be used to complete your task. And if all else fails, you are never afraid to engage in combat, being capable of dealing high amounts of burst damage while dodging your way past opponents. 

As a Gangster, you typically will be the voice of your party as you make good use of your silver tongue. You are a criminal at heart but are capable of taking care of business out in the open. Your stealthy abilities are used to move in plain sight, rather than sneak through the darkness. Most Gangsters work for a crime lord or mob boss either directly or indirectly. You work to enrich yourself and your criminal network, but ultimately your motivation is self-centered. Your devotion to your boss only extends to the point at which it benefits you; past that, all bets are off. 

Infiltrate, negotiate, and if you choose, retaliate. That is the Gangster.

Gunman's Guile

When you choose this archetype at 3rd level, you develop a knack for talking your way out of trouble and blasting your way out if that were to fail. A Gangster's first tool in their arsenal is their wit, always starting off any encounter by talking your way into your desired outcome. Depending on your playstyle, you may wish to emphasize on different areas of negotiations. Some Gangsters will bribe their way into their desired outcome, taking every opportunity to assure to their interlocutor that there will be a mutually beneficial conclusion to their business dealings. Others may simply pull out their shotgun, aim it at someone they are intimidating, and make a very clear, yet simple demand. Additionally, your years in the underground crime networks has allowed you to browse a great many weapons, many of which are illegal in your city. Because of this, the Gangster has grown keen on using firearms as they are quite an effective "business" tool. 

You gain proficiency in Firearms and one of the following: Persuasion, Intimidation, Performance, and Deception. 

Crimeboss Crackshot

You have found that getting the job done swiftly often yields the best results for you and your network. Knives and guns are the Gangster's favorite tools, one being a viciously loud and deadly weapon, and the other being a sly and easily concealable blade. Precision is the name of the game, which is why when you strike, you make sure to strike fast and hard. Due to this, the Gangster has been known to unload a colossal amount of damage all at once.   

Once per long rest, you may double the amount of Sneak Attack dice used in an attack with a firearm or dagger.
(Example: at 3rd level you may use 4d6 once instead of 2d6, and at 9th level you may use 10d6 instead of 5d6)

Scoundrel's Shuffle

There is one guarantee as a Gangster, something will eventually go wrong. And in your line of work, things going wrong usually results in loss of gold, resources, or blood. However, as a professional, you have learned to adapt to some of the worst situations you find yourself in. Your skills allow you to seemingly sneak on and off of the battlefield without falling victim to an attack. 

As a bonus action, you refresh your available movement (to a maximum of 30) and can move without provoking opportunity attacks for the rest of your turn.
You can use this ability 3 times per long rest.

 

Extra Attack

Your offensive capabilities as a Gangster have grown as you are now able to be even more lethal each turn. 

You can attack twice, instead of once, whenever you take the Attack action on your turn. 

The Boss

Your reputation has spread far and wide, amassing an immense collective respect from the criminal underground of the world. You are a careful person, so most don't actually know your name; however, when traveling to a new city or communicating with your contacts, you are referred to only as 'Boss'. As a Gangster, you know very well that when someone in your profession is dubbed the 'Boss', there is a massive target put on your back. With this in mind, you have amassed the skills necessary to not only make achievements within the criminal underworld, but rule it. 

You may double the amount of Sneak Attack dice used in an attack with a firearm or dagger. You can use this feature a number of times equal to your Charisma modifier (maximum of 4).
(Example: at 3rd level you may use 4d6 once instead of 2d6, and at 9th level you may use 10d6 instead of 5d6)