A prominent ship captain was banished by the local navy of a powerful city-state (name suggestion: Greatwhelm) on the bay. Now, he has returned with a massive man-of-war, capable of leveling the city itself with cannon fire. He arrives at port to make a proclamation, backed by a number of his followers.


A little over a year ago, this Captain (name suggestion: Brand Atherton) was hailed as a hero by the city-state, having won numerous battles against rivals at sea. However, it was discovered that he had been embezzled nearly ten thousand gold pieces and was banished from the city forever. He sailed away in his ship (name suggestion: The Loyal Griffon) and hasn’t been heard of since.

Now, the Captain has returned in a new ship: a massive man-of-war with over one hundred cannons. Manned by pirates, his force likely couldn’t overcome the city itself, but they could certainly take down most of the city’s weakened and inexperienced navy.


The Captain arrives by rowboat with a small band of goons and declares the city is being held hostage. He makes the proclamation and demands a ransom of one million gold pieces, before yelling at passerby that they are welcome to join him.

The Captain is sharply dressed, sports a carefully cut beard, and an absurd number of medals on his breast. He’s armed with a cutlass and a sharp wit—he speaks carefully and snips the end of his words.

A prominent Noble (name suggestion: Lady Silverfable) watches carefully, correctly assuming this ego-boosting proclamation is the best chance the city has at stopping the madman before the situation escalates out of control.



There are 2 main parties interested in the conflict:

  • The Captain: His crew of pirates are mercenaries, loyal only to his gold. If he doesn’t secure the funds from this city, he’ll be unable to pay them and likely be murdered. In addition, he despises the Noble and wants to see her dead.
  • The Noble: The ringleader of the city’s rulers, she wants to keep the city securely under her thumb. She knows providing the ransom will inevitably lead to the end of her reign, if not by bankrupting her but by displaying weakness to her rivals. She wants to see the Captain slain and her coffers filled.

Using These Encounters

What do your player characters want? What are their best and worst qualities? What goals are they pursuing? Read through a few of the examples below, then choose the encounter that best suits your situation.

  • If you have player characters who are pious or helpful, or who like to defend the weak, run Encounter C. If, on the other hand, they are greedy or uncaring, run Encounter B.
  • If you have player characters who want to gain political or social favor with a local faction, run Encounter A. If you have player characters who want to uphold certain vows, or to gain favor with their gods, run Encounter C.
  • If you have player characters who need information from or about a criminal element in the city, run Encounter B.
  • If the player characters are working to foil some kind of villainous plan, run Encounter A.

If the player characters are just looking to make a quick buck, run Encounter B.

Encounter A

In this encounter, the Captain attempts to execute a few civilians to prove his point and to kidnap some more to reinforce the ransom.

Setting up this Encounter

This encounter involves a hostage negotiation. If you have player characters who want to gain political or social favor with a local faction, then the hostage is the Noble. She is taken captive the moment the Captain arrives on shore, where her already bribed bodyguards hand her over.If you have player characters looking to foil some kind of villainous plan, then the hostages are five peasants, one of which the Captain prepares to execute with his cutlass after announcing his intentions.


The Captain has his hostages, and announces to all bystanders that the city now belongs to him—he’s holding the ships in the bay and these prisoners hostage until he’s been paid a ransom of one million gold pieces. He holds his cutlass to a hostage’s throat and requests to the only nearby city guard that they run along and deliver his ultimatum.

If the players attempt to attack, the Captain tries to use his hostages to cover his escape. Barring that, he’ll order his goons to keep enemies at bay while he tries to escape in the rowboat, fighting only as a last resort. Should he escape successfully, the Captain sinks a ship or two in the bay, or possibly even opens fire on the city itself depending on how enraged he is after the battle.The number of allies the Captain possesses depends on the level of the party. For a party of around 4th level, he has around 5 thug followers on shore with him. Alternatively, for a more chaotic battle, he may have as many as 10 or more bandit followers instead.

Resolving this Encounter

When this encounter finishes, your players who want to gain political or social favor with a local faction should hopefully curry some favor with the Noble for their efforts. If she is no longer alive after the encounter, it’s possible that her compatriots are still grateful that the hostage negotiation is over, although depending on how the situation was handled, they could possibly be angry with the party instead. They likely reward the party with gold and connections.If your players wanted to foil some kind of villainous plan, they may need to take the fight to the Captain’s ship to end the chaos once and for all. The grateful city is likely to reward the party with gold, and they may even be able to commandeer the Captain’s vessel.

Encounter B

In this encounter, the Captain calls for an uprising from the surrounding civilians, promising them great reward if they will but join him.

Setting up this Encounter

This encounter involves the Captain attempting to create a mass riot among the bystanders, using the chaos to incite panic at his demands. If the players are greedy or uncaring, they may wish to join the Captain and reap the rewards he can provide. He’ll put up a massive prize on the Noble’s head, possibly as much as 500 gold pieces, but she’s brought a gladiator bodyguard.

If the players need information from or about a criminal element in the city, then the Captain is willing to provide it for their contributions. He is openly affiliated with this faction, and this is a chance for the players to endear themselves to him.If the players are just looking to make a quick buck, the Captain offers them 75 gold per head of a town guard and 300 gold for their leader instead of the original rates.


The Captain arrives on the docks, proclaiming to all that the city is going to fall—he claims everyone can choose to die here or join him and reap the rewards.

The members of the city guard present immediately move in—a veteran (their leader) and 4 thugs. The Captain immediately declares he’ll give 50 gold pieces to any who bring him the head of a city guard member here, and 200 to anyone who gives him the head of their leader.

If the party takes up the Captain on his offer, the guards show no quarter. The Captain offers no help, although if anyone attacks him, he won’t stop until they’re dead. He does offer passage to his ship, however, and makes good on the offer of gold.

Resolving this Encounter

Player characters who are greedy or uncaring are given ample rewards for their work—and the opportunity to do more. The Captain has no shortage of bloody tasks to hand out, and no desire to do any of it himself. He might enlist the party to assassinate more nobles, or he may ask them to carry out some other violent tasks as part of his crew.

Player characters who need information from or about a criminal element in the city, the Captain is willing to discuss propositions to those who cause enough mayhem in the city, especially any nobles.Player characters who are just looking to make a quick buck are rewarded greatly for their efforts, possibly even more than the Captain promised. He can offer them more in the future.

Encounter C

In this encounter, the Captain immediately opens fire on the city, more concerned with revenge than money.

Setting up this Encounter

This encounter involves a disgruntled customer, which gives us some flexibility. If your player characters are pious or helpful, or who like to defend the weak, then citizens cower as cannonballs rain from above. Pirates flood the street, people scream, and entire buildings crumble. The main goal can become rescue rather than escape.If the PCs want to uphold certain vows, or to gain favor with their gods, the Captain is strongly connected to a faction they oppose. For example, he may have paid for his mercenaries through his association with a rich church opposed to the party, or perhaps he employs an order of paladins that have crossed paths with the party. In this case, the cannonfire is mostly constrained to the bay, and the main threat is the pirates attacking from the docks. A priest may be one of the victims of the chaos.


With little warning or ceremony, the cannonfire starts and the chaos begins. Nearby buildings collapse and pirates arrive to loot. Characters that don’t get behind some sort of solid cover within a few moments must succeed on a DC 13 Dexterity saving throw or take 2d6 bludgeoning damage at the start of a turn from the chaos.Anywhere between 6 and 12 bandits attack as well. Around 4 peasants are in trouble—trapped under rubble, at the cutlass point of a pirate, or otherwise in danger. They attack anyone who looks weak, trying to take their valuables. If attacked, they prefer to gang up on a single foe and take hostages.

Resolving this Encounter

For player characters pious or helpful, or who like to defend the weak, those they save are extremely grateful. The fight possibly goes to the man of war itself, or the general populace is forced to flee the city entirely. The people they save are more than willing to offer food, shelter, and any information they have.Parties who want to uphold certain vows, or to gain favor with their gods may be rewarded in goodwill from the religious factions of the area. They could be granted information, a holy rite, or safe passage out of the city, if it comes to that. If they are allied with a specific religious faction, those saved may wish to join such them, bolstering the organization’s strength.