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Previously on Tomb of Annihilation

Mannix, level 5 Human Inquisitive Rogue/Wizard
Khaless, level 5 Half-Drow Assassin Rogue
Gillian, level 5 Triton Bard of Whispers
George, level 5 Tortle Battle Master Fighter/Rogue
Therin, level 5 Hill Dwarf Druid of the Moon

In all our years of playing Dungeons & Dragons, we’ve never come as close to a total party wipe as this week’s session. The bar fight within Boscoe’s Bilge, the tavern at the hidden pirate base of Jahaka Anchorage, proved a bloody, drawn-out struggle as the party threw everything they had at the third and final pirate crew.

The session opened by rolling initiative. Negotiations with Captain Laskilar had proven ineffective – he knew who they were and coveted all the magical loot they’ve acquired from their adventures in Chult. He was surrounded by his fellow pirates and supremely confident, even when Khaless responded by knifing the nearest pirate in the face.

The battle consisted of about half a dozen pirates (CR 1/8 bandits), five thugs including the tavern keeper (CR 1/2), the tavern keeper’s pet deinonychus Knuckles (CR 1), Laskilar’s sea priest (CR 2), half-orc first mate (CR 5 gladiator), and the Captain himself (CR 2).

Other than the hulking half-orc, none of these enemies were noteworthy; a bunch of cannon fodder. But a funny thing happened – the dice were on fire for me. These lowly +3 and +4 attacks were hitting left and right, even versus the AC 17/18 party members, and often doing close to max damage every time. The close quarters of the bar meant they were all getting attacks off and could utilize half to 3/4 cover with the tables and bar.

Khaless smartly took out the priest with her powerful assassin strike, removing him before he could even get a turn. But the real power lie in the gladiator, whose shield bash and spear combo nearly downed Gillian in the first round, causing her to turn invisible, flee, and heal rather than shut down the hordes of pirates.


Mannix kept the pirate captain busy via some illusion trickery in a nearby room, while Therin summoned apes on each table. His concentration was broken after several attacks, and he responded by summoning an allosaurus right in the middle of the bar, which would hang around for several rounds tanking and dishing lots of damage.

But these pirate were a hardened crew. They knew to focus on the spellcasters.

After wild shaping Therin was forced back to his dwarf form from the onslaught of attacks and retreated outside. Mannix had do dive threw a window to avoid the pirate captain. Both would end up going down later in the fight. George would go down as well when the bartender joined the battle, and both Therin and Gillian were forced to use most of their spell slots and turns simply healing and keeping the team alive.

The DM was supremely satisfied to see multiple one-use potions and scrolls get used.

We haven’t had a fight where the majority of the party goes down since like, week 2 of Storm King’s Thunder when we were level 1.

That half-orc had over 100 hit points, three powerful melee attacks, and a 16 AC. At one point he was fighting George, Khaless, and the summoned Allosaurus all at once. Once Khaless was able to carve her way through the bar the tide began to shift in their favor, and she could help defeat the enemies who chased Therin outside while George and Gillian dove behind the bar and to mop up the rest.

The captain was never attacked at all. Despite the heavy injuries on the party’s side, most of his crew lie dead, strewn around the bar. He swept his magical cloak around him and vanished in a puff of smoke, but the rest of the pirates died to a combination of Khaless’ blades, George’s bow, and a potion of fire breath from Gillian.


Nobody made it out of that fight with more than about 20% hit points remaining, and Mannix sustained a crippled arm lingering injury. It was a hell of a fight made fun for how tense it was, and how close to disaster the party came. Even then, Laskilar was able to escape, creating some interesting consequences.

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