Goblin Boss

A goblin boss as ally is a guide-for-hire situation, a hostage situation that thawed into rapport, or the result of a bigger threat (an orc warband, a dragon's tax) forcing it to throw in with the party. It is still chaotic, still self-interested, and still the smartest goblin in the room. Treat it as an NPC contractor, not a friend.

In a fight, the boss is most useful as a flanker for the rogue and a bow-and-bolt nuisance from cover. Two Shortbow attacks at +4, range 80/320, with the bonus +1d4 if it had Advantage from Hide. Run a turn as: Hide (bonus action via Nimble Escape), then two Shortbow attacks with Advantage. That's a credible 5 to 9 damage twice from a hidden position. Keep it within 5 ft. of a tankier party member and Redirect Attack now defends a key NPC, since the boss will gladly trade an attack roll's worth of cover to keep its meal ticket walking.

The exit is bribery. The boss serves until the agreed payment is in hand or until something more profitable walks past. Pay in coin, in safe passage, or in another goblin's head. If the party tries to get loyalty for free, the boss bolts the moment a fight goes sideways, and it knows where their camp is.

Have the boss steal one small thing on the way out: a knife, a holy symbol, the cleric's spare boot. The petty theft is the only sentimental gesture goblins know.

A goblin boss is the cornered animal who survived a rougher goblin than itself, and you should run it as the smartest coward at the table. It opens engagements from cover, never picks the front rank, and has at least three lesser goblins or worgs nearby to absorb whatever the party throws first.

The whole encounter pivots on Redirect Attack. As a reaction, when something the goblin can see attacks it, the boss swaps places with a Small or Medium ally within 5 ft. and that ally takes the hit. So mob it. A boss surrounded by four goblin minions is effectively four extra HP pools, and the rogue's first big sneak attack vanishes into a kobold-shaped meatshield. Pair this with Nimble Escape (Disengage or Hide as a bonus action) and the boss can break line of sight every single round, popping out from behind a wagon, throwing two Shortbow shots at +4 for 5 piercing each, then ducking back. Indoors, the Multiattack with Scimitar at +4 for 5 (plus 2 more if it had Advantage from Hide) makes the boss a flanker that always opens with surprise damage.

Bosses do not die for the cause. At Bloodied (10 HP) it tries to bolt, ideally toward a trap it set, a rope bridge it can cut, or a bigger monster it has been managing. Stealth +6 means a successful Hide is the goblin's parting trick. Capturing it alive is the better story, since a goblin boss negotiates fast: it sells the next chamber, the warlord one camp over, and the price of its own freedom in a single sentence.

Have the boss insult one PC by name (Common is on the language list) the first round it acts. The party will hate it correctly, and the dead goblin sticks in their memory.