Bandit Boss

Leadership (Recharges After Short or Long rest). The Pirate Captain utters a command whenever a friendly creature that it can see within 30 feet of it makes an attack roll or a saving throw. The creature can add a d4 to its roll provided it can hear and understand the Pirate Captain. A creature can benefit from only one Leadership die at a time. This effect ends if the Pirate Captain becomes incapacitated.

Flourish. The Bandit Captain adds its Charisma modifier to the damage roll for its longsword attacks (included in the attack).

Sea Legs. The Bandit Captain has advantage on ability checks and saving throws to resist being knocked prone.

Multiattack. The captain makes three melee attacks: Three with its Longsword. Or the captain makes two ranged attacks with its Hand Crossbow.

Longsword. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: # (1d8 + 5) slashing damage, or 10 (1d10 + 5) slashing damage if used with tow hands.

Hand Crossbow. Ranged Weapon Attack: +5 to hit, range 30/120 ft., one target. Hit: 6 (1d6 + 3) piercing damage.

Shape Up, Ye Dog (2/day). Whenever a friendly creature within 30 feet of the Bandit Captain that can hear it misses with an attack, the captain can yell perilous threats to allow that creature to re-roll their attack roll.

Parry. The Bandit Captain adds 2 to its AC against one melee attack that would hit it. To do so, the Bandit Captain must see the attacker and be wielding a melee weapon.