The Buccaneer — Sagor från Valoris

You never learned to be quiet. Where other rogues wait in the dark for one clean opening, you take the deck, name the odds, and start singing — and somehow the crew fights harder, the enemy fights worse, and the whole brawl tilts your way. You are not an assassin. You are the reason your side wins.

Your craft is Momentum: the swing a fight takes when someone bold refuses to give ground. It comes from standing where the steel is, from the first cut and the last, and you spend it as fast as you earn it — on a dirty trick, or a shanty that puts the fire back in your crew. Stand still and you have nothing. Press forward and you are unstoppable.

The Archetype

Rogue Level	Feature
3rd	Buccaneer's Swagger — Momentum, Cutthroat Techniques, Battle Shanties
9th	Veteran of the Black Wake
13th	Master of the Rolling Tide
17th	Pirate Legend

Level 3

Buccaneer's Swagger

You fight like a captain, not a cutpurse. You gain proficiency in Persuasion or Intimidation (or Expertise in one of them, if you're already proficient) — a reputation is a weapon, and you keep yours sharp.

Momentum

You begin each combat with 0 Momentum, and can hold a maximum equal to your Proficiency Bonus. Unspent Momentum fades when the fight ends. You gain Momentum as follows:

The first cut. When you deal Sneak Attack damage, you gain 1 Momentum.
The last. When you score a Critical Hit or reduce a creature to 0 Hit Points with a melee attack, you gain 1 Momentum.
Holding the deck. If you haven't gained Momentum this turn and you end your turn within 5 feet of a hostile creature, you gain 1 Momentum.

You spend Momentum on Cutthroat Techniques and Battle Shanties, below.

Cutthroat Techniques

When you hit a creature with a melee weapon attack, you can spend Momentum on one technique. (Two at 13th level, paying for each.)

Technique	Cost	Effect
Vicious Opening	1	The attack deals an extra 1d6 damage (increasing to 2d6 at 13th level).
Crippling Blow	1	The target's Speed is reduced by 15 feet (to a minimum of 0) until the end of its next turn.
Exposed Target	1	The next attack roll made against the target by an ally, before the start of your next turn, has Advantage.
Dirty Trick	1	The target must succeed on a Constitution saving throw (DC 8 + your Dexterity modifier + your Proficiency Bonus) or it can't take Reactions until the start of your next turn.

Battle Shanties

As a Bonus Action, you can spend 1 Momentum to strike up a shanty. It affects any number of allies of your choice within 15 feet (30 feet at 9th level) who can hear you, and lasts until the start of your next turn.

Shanty	Effect
Heave Away	Each affected ally's Speed increases by 10 feet, and they don't provoke Opportunity Attacks when they move.
Hold Fast	Each affected ally gains Temporary Hit Points equal to your Charisma modifier + your Proficiency Bonus.
No Fear of Drowning	Each affected ally can immediately end the Frightened or Charmed condition on itself, and has Advantage on saves against those conditions.
Pull Together	The first time each affected ally hits with an attack, it deals an extra 1d6 damage.

Level 9

Veteran of the Black Wake

You have been boarded, keelhauled, and rigged for worse, and none of it stuck. You gain the following benefits:

Fancy footwork. When you hit a creature with a melee attack, that creature can't make Opportunity Attacks against you for the rest of your turn.
Rigging-born. You have a Climb Speed equal to your Speed, and difficult terrain doesn't slow your Climb.
Never cold-started. You begin each combat with 1 Momentum instead of 0, and your Battle Shanties now reach 30 feet.

Level 13

Master of the Rolling Tide

Your command of a brawl is total. You gain the following benefits:

Two tricks at once. When you hit with a melee weapon attack, you can apply two Cutthroat Techniques instead of one, paying the Momentum cost of each.
Captain's Command. Once on each of your turns, you can spend 2 Momentum (no action required) to shout an order at an ally within 30 feet who can see or hear you. That ally can immediately use its Reaction to either move up to half its Speed without provoking Opportunity Attacks, or make one weapon attack.

Level 17

Pirate Legend

Your name has outgrown you, and fights bend around it. Your maximum Momentum increases by 2, and when you reduce a creature to 0 Hit Points, each ally within 30 feet who can see it gains Temporary Hit Points equal to your Charisma modifier.

And once a fight, you can call the whole crew down on them. As a Bonus Action, you can give the Captain's Call: each ally within 30 feet who can see or hear you may immediately use its Reaction to move up to its Speed and make one weapon attack. You then regain Momentum up to your maximum. Once you use the Captain's Call, you can't do so again until you finish a Long Rest.