Brigand

Brigands are as much thugs and enforcers as they are thieves, favoring brute force over cunning deceit in numerous engagements, but still retaining the ability to employ stealth and finesse when needed. Brigands enjoy several benefits more commonly seen among fighters, including access to a wider array of weapon and armor choices, but do not sacrifice any of their inherent roguish talents.

Rough and Tumble

Brigands are hardier than typical rogues, being harder to take down and more liable to engage in a frontal fight. Brigands enjoy an additional 1 HP per level.

Combat Training

Through extensive training, a Brigand has improved their physical abilities and knowledge extensively in the ways of combat. Starting at 3rd Level, Brigands gain the Moderately Armored Feat as a bonus feat, and gains proficiency in any two (2) Martial Weapons.

Improved Brigand Combat Training

Brigands are far more liable to engage in a frontal fight, but will also turn whatever fight they are in to their advantage. Starting at 9th Level, they gain an Extra Attack, and can employ this extra attack from Stealth so long as they make both attacks before moving, receiving their sneak attack damage (if applicable) to both of these attacks. If both attacks are made from stealth, the Brigand loses Stealth after the second attack is made.

Further, through extensive training in their usage of Medium Armor, Brigands gain the Medium Armor Master Feat.

Ambush Attacker

Brigands are more than capable in a direct fight, but at the end of the day they will always choose an ambush if it's possible. Starting at 13th Level, Brigands add their Proficiency Bonus to Initiative Rolls. Further, if starting their initiative from Stealth, the first attack a Brigand makes that is not at long range can roll its damage and sneak attack damage twice, taking the higher damage rolls for each.

Expert Ambusher

Starting at 17th Level, the Brigand has become an expert at ambushing their enemies, granting them Advantage on all Initiative Rolls. Further, they gain a number of special options they can employ when delivering a sneak attack. Any time a Brigand delivers Sneak Attack Damage, they can choose one of the following maneuvers to employ as a bonus action:

Body Shield. Attempt to engage in a grapple with a target of equal or smaller size with Advantage on your Strength Check. If you succeed, you lose stealth, but the target is grappled and held against you. Neither you, nor the grappled target fall prone. Instead, your movement is halved, and you have to roll an opposed Strength (Athletics) Check against the grappled target's STR Saving Throw each time you move with them grappled. If the target succeeds a STR Saving throw, the grapple ends at the end of the movement, and you regain the other half of your movement speed. You can freely choose any unoccupied space next to you to put the grappled target in after each 5ft movement. All attacks from the same direction as the target is from you are made at disadvantage, and any such attacks that fail to hit you instead hit the grappled target. These attacks cannot deal critical damage to the grappled target.

Onslaught. Move up to 1/2 your remaining movement and make another attack with any held weapon against another target in range from the new position with advantage, even if you normally would have lost stealth. You lose stealth after making the second attack.

Snatch Victim. You attempt to grapple a target up to one size larger than yourself with Advantage on your Strength Check. If you succeed, you may move up to 1/2 your remaining movement with the grappled target, then both you and the grappled target fall prone. The target is silenced in addition to being grappled, and you may attack at advantage with a one handed melee weapon, unarmed attack, or natural weapon against the target so long as they are restrained. If you end your movement out of line of sight from all enemies, you do not lose stealth.

Take Down. You attempt to knock the target of your attack prone. They must succeed a DEX Saving Throw against a DC(8 + STR Mod + Proficiency Bonus) or be knocked prone by the sneak attack. This may be used in between your first and second attacks if making your extra attack action this turn.