Tough Boss

A tough boss ally is the captain the party hired, the city watch sergeant who agreed to back them up on a raid, or a former enemy who switched sides when the party offered better terms than the previous employer. They are professional, transactional, and clearly in command of their own people. They expect to be paid in coin or favor, they expect to be told what the plan is, and they expect their crew to come home.

In combat, the boss leads from the front line. Multiattack with two Warhammers at +5 for 12 bludgeoning each, Pack Tactics Advantage as long as one of their crew is in melee with the target, and a 10 ft. push on every hit. Position the boss next to a party member and the boss attacks at Advantage; position the party member next to the boss and the same is true. This is a real action-economy boost for low-Tier-2 parties and worth setting up explicitly. The Heavy Crossbow Multiattack at +4, range 100/400 ft., 13 piercing per bolt is the long-range option when the boss is asked to overwatch.

The boss will not throw their crew into a meatgrinder for the party's sake. If a PC orders a suicidal charge, the boss either refuses or renegotiates the contract on the spot. Pay them on time, keep them informed, and they will work with the party again. Try to use them as expendable shock troops and they will leave mid-mission.

Have the boss check in with their crew by name at the end of every fight. Players will start remembering the crew names too, and the day a crew member dies will hit harder than the day a generic NPC does.

A tough boss is the lieutenant in chain mail who runs a bandit camp, a smugglers' wharf, or a goblin warband that has hired up. The stat block is a mid-tier human with Pack Tactics, which is the entire reason to use it: alone, the tough boss is a CR 4 with two attacks and 82 HP. Surrounded by two or three minions, the tough boss attacks at Advantage on every swing, and that is the encounter. Never run the tough boss solo. Always run them with at least one warm body within 5 ft. of the target.

Open at range if there is space. Heavy Crossbow at +4, range 100/400 ft., 13 piercing per bolt, two bolts per Multiattack averages 26 damage on full hits. Pair the boss with a Bandit or Tough on the front line and the boss stays back, picking off the wizard from a balcony or a cart. Once the party closes, drop the crossbow and switch to Warhammer: +5, reach 5 ft., 12 bludgeoning, and Large or smaller targets get pushed 10 ft. straight back. Two Warhammer attacks per round with Pack Tactics Advantage and a 10 ft. push on each hit is genuinely disruptive, because the rogue keeps getting shoved out of Sneak Attack range.

The boss is not stupid. Int 11 means real plans, real escape routes, real awareness of which PC is the threat. Identify the highest-damage enemy and focus the warhammer on them, using the push to keep them off balance. If the boss is Bloodied (41 HP) and the minions are gone, the boss surrenders if the party offers terms. If the party does not, the boss runs for the predetermined exit. Toughs are mercenaries, not martyrs.

Name the boss, give them a scar, and let the party hear about them from a captured minion two scenes before the fight. A boss who shows up unexpectedly is a stat block. A boss the party has heard of is a story.