The Bandit Captain Rogue

Roadside Warrior

When you chose the Bandit Captain Archetype at 3rd level, you gain proficiency in medium armor and simple and martial weapons, as well as improvised weapons. Additionally, you gain proficiency in the Athletics skill, or expertise if you are already proficient in Athletics.

In addition, also at 3rd level, you gain another way to use your Sneak Attack. You can add your Sneak Attack damage to any weapon damage roll made with a weapon with which you are proficient, provided you have advantage on the roll, or another enemy of the target is within 5 feet of it, that enemy isn't incapacitated, and you don't have disadvantage on the attack roll.

Prince of Thugs

Also at 3rd level, you learn to better command your underlings. You have advantage on all Charisma (Deception, Persuasion, Intimidation, and Performance) checks made towards your Sidekicks and Followers, or, at your DM's discretion, any creatures in your employ.

Professional Kidnapper

At 9th level, you don't need advantage to Sneak Attack an enemy as long as you are grappling them. In addition, if you use the Attack action to attempt to grapple an opponent, you can make a single melee attack against them as a bonus action.

Riposte

At 13th level, you learn to defend yourself and strike back in the same motion. When you take the Uncanny Dodge reaction, you can make a single weapon attack as part of the same reaction.

Great Cleave

At 17th level, your mastery of arms allows you to hew through multiple opponents at once. When you make a melee weapon attack, you can target two creatures or objects, rather than one, provided that both are within 5 feet of you. Make a separate attack roll for each target. You may apply your Sneak Attack damage to each target, provided that the other conditions for Sneak Attack are met for that target.

Image Credits

https://www.artstation.com/artwork/v1r3Za https://www.artstation.com/artwork/KodNR https://www.artstation.com/artwork/m2Jvy