
Halgrin |

Halgrin approached the green Dragonborn, knowing full well that this meeting could end in someone's death. But he couldn't risk another pirate encounter with his team. Captain Pike was likely suspicious enough already and even now some of their sabotage could be discovered after the fact.
"Greetings, friend. My name is Halgrin of Waterdeep. My friends and I noticed that you weren't comfortable with the Captain's actions against Olivia. Perhaps we could talk?"

Halgrin |

"Stuck here? So you're not a member of this crew then?"

Halgrin |

Halgrin nods gravely.
"So you were press-ganged. And that means that he'll do the same to us or just kill us outright. I'm guessing you don't have any particular allegiance to Pike then, and probably wouldn't mind if he gets taken down a peg. I'm not saying I would need you to do anything dangerous. Just look the other way, as my friends and I handle him. If you do this, I can guarantee you your freedom."
I guess a Persuasion check?
CHA (persuasion): 1d20 + 0 ⇒ (16) + 0 = 16

Halgrin |

"That's fair enough. My team will handle the rest. As I said, my name's Halgrin."
He offers his hand to the dragonborn to shake.
"What's yours?"
Whether the dragonborn introduces himself or not, Halgrin nods politely and returns to the rest of the party. He then relays the situation to them.
"There's no other choice here. We have to take down Pike. And hopefully do it quickly and quietly enough to keep casualties to a minimum. Does anyone here have a different take? Because I won't lie, I'd love to hear one."

Horat "The Bulwark" |

"Horat of Unther.", Horat says as he extends his own hand and quiet presence.

Olivia "Liv" Moore |

Olivia desperately wished she could think of another way out of this situation, but she couldn't. She agreed that Halgrin was most likely correct about the captain's plans, but it also felt wrong to try for a pre-emptive when they couldn't be certain of his plans. But could she really risk the lives of these people by arguing to give the captain the benefit of the doubt? They had helped look after her thus far, so how could she repay them by questioning their wisdom when they were clearly more aware of the ways of the world than her? Sadly, she shook her head, indicating that she had no better ideas, and waited to hear what the plan would be.
I would guess either use Olivia as a distraction or try to attack him as he sleeps. As he sleeps seems less likely to involve the rest of the crew (since I'm assuming he has his own room), but it probably also means we'd be fighting in more cramped quarters. Also, the gun isn't exactly stealthy, so if we used that, we'd have to bottleneck his reinforcements.

Enizver |

Enizver was happy enough to shoot the man. Killing people without warning wasn't his way, however. "I'd suggest letting me hide, and confronting him. If he refuses to back down I'll shoot him, and we can hopefully finish him off before the rest get too involved. Or hurt. And then we own a boat!"

Pawn's Dilemma GM |

Looks like it's time for that nudge!
The sailor currently manning the crow's nest cries out "Land sighted!" Pike grunts and nods. Then he bellows to everyone on deck "Ready to make port! We're pulling into Nyanzaru, lads!"
Since it's been a long time, I'll remind you Port Nyanzaru is your destination in Chult.

Wrinil son of Pel of Waterdeep |

Huh, I was anticipating our arrival to take longer and be more arduous, Wrinil thinks to himself.

Horat "The Bulwark" |

Uncaring of the heat, Horat is in full armour.
If challenged, he will reply.

Ol' Pike |

While you're still quite distant from Nyanzaru (too far to make it out in any detail) Pike stalks over to where you stand. "Get below! And hand over your weapons and armor!" The big man stands before you, boarding pike in hand and wearing armor of his own. Several of his pirates stand around, hands near their weapons, but they look confident in their captain's ability.

Enizver |

Enacting his plan, Enizver found a place to sneak off to incase the Captain didn't see reason. He also focused on studying the captain, for a follow up shot. The Gnome did not expect the man to do this sensibly.
Stealth: 1d20 + 7 ⇒ (3) + 7 = 10
Stealth: 1d20 + 7 ⇒ (9) + 7 = 16
Insight: 1d20 + 5 ⇒ (18) + 5 = 23

Ol' Pike |

"What's this?! Raising your hand? Get below!!" Pike steps menacingly toward Wrinil.

Olivia "Liv" Moore |

"I think he just has a question?" Olivia starts slowly pulling out her weapons to hand over; it's not like she actually needed them anyway. Out of the corner of her eye, she watches for a signal from the more martial members of the group.
I'm back.

Wrinil son of Pel of Waterdeep |

"B-but," Wrinil stutters nervously, "what if I don't have any weapons or armor?"

Ol' Pike |

"THEN JUST GET BELLOW!!!!" the captain roars in Wrinil's face, spraying him as he does so. Somehow... Pike's saliva is quite salty...
Showing disposition on map in case you guys decide to try something.

Wrinil son of Pel of Waterdeep |

"O-okay," Wrinil stammers and begins going below deck.

Halgrin |

Halgrin quickly finds the face of the dragonborn Wex to see if this was the moment that they should attack.
I'm guessing an insight check here for that information. If Halgrin is unsure about what Wex's face is trying to say, his reaction will be to rush the Captain.
WIS (insight): 1d20 + 2 ⇒ (3) + 2 = 5

Olivia "Liv" Moore |

Seeing that she is not in a great position, being both squishy and right next to the very large captain, Olivia quickly pulls out her broom and flies directly upwards 30 feet before she begins casting a spell to bolster Horat and Halgrin.
Action: Disengage, Move, Bonus action: Twinned Shield of faith to give Horat and Halgrin +2 AC
Concentration: Shield of faith

Ol' Pike |

AoO: 1d20 ⇒ 16
Dam: 1d10 + 3 + 1d8 ⇒ (3) + 3 + (8) = 14
Liv str save: 1d20 ⇒ 9
Fall damage: 1d6 ⇒ 2
AoO: 2d20 ⇒ (9, 5) = 14
Dam: 1d10 + 3 ⇒ (7) + 3 = 10
Liv conc w disadv: 2d20 ⇒ (2, 7) = 9
Even though Olivia thinks she is leaving carefully, the captain still swings his pike with blistering speed, striking her hard in the side (14 damage) and pulling her down to the deck where she lands hard (2 fall damage and prone). Then when she tries to cast her spell, he strikes her again with the pike in the shoulder (10 damage). She tries to focus on the spell but the intimidating captain standing over her makes it very difficult (concentration with disadvantage failed).
Sentinel feat. Battlemaster's trip attack. Mage slayer feat.
Enizver may still go.

Enizver |

As soon as the blow landed Enizver squeezed a trigger, aiming to blow as large a hole in the captain as possible. He'd have prefered more of a warning, but he wasn't going to allow that attack either.
To Hit: 1d20 + 5 ⇒ (19) + 5 = 24
To Hit (Advantage): 1d20 + 5 ⇒ (2) + 5 = 7
Damage: 2d6 + 3 ⇒ (5, 6) + 3 = 14
Thunder Monger: 1d6 ⇒ 2
Sneak Attack: 2d6 ⇒ (1, 2) = 3

Ol' Pike |

Attack liv: 2d20 ⇒ (19, 14) = 33
Attack Horat: 1d20 ⇒ 14
Dam Horat: 1d10 + 5 ⇒ (4) + 5 = 9
Daggers Horat: 3d20 ⇒ (16, 1, 6) = 23
Daggers Halgrin: 3d20 ⇒ (6, 5, 11) = 22
Dam horat: 1d4 + 5 ⇒ (2) + 5 = 7
Cutlasses E: 2d20 ⇒ (10, 6) = 16
With a quick jab of his boarding pike, the captain stabs Liv in the side and she passes out from blood loss. He then moves past the mast while striking at Horat (hits for 9 dam). He takes up a poised position in the center of the ship and, grinning, says something to taunt Horat and Halgrin. But, oddly enough, nothing can be heard. Pike looks perplexed by this. Two of the pirates on deck rush Enizver and strike at him with their cutlasses but can't manage to land a blow. Six other pirates throw a dagger each at Halgrin and Horat but as blades fly all over the deck, only one manages to strike Horat in the leg (7 damage).
Party GO!

Wrinil son of Pel of Waterdeep |

Wrinil rushes over next to Liv, pulling out some simple cloth wraps, and saying a prayer along the way. Once he gets to Liv he quickly tends to her gash.
Casts Sanctuary on himself
Medicine: 1d20 + 7 ⇒ (5) + 7 = 12

Horat "The Bulwark" |

Distracted momentarily by Pike's brutal strikes against Olivia, Horat suffers a strike himself.
He grits his teeth, and advances upon Pike, the silvered head of his halberd glittering in the sun. He will let that speak for him.
Booming Blade: 1d20 + 5 ⇒ (1) + 5 = 6
Damage: 1d10 + 3 ⇒ (3) + 3 = 6
Halberd End: 1d20 + 5 ⇒ (11) + 5 = 16
Precision Attack: 1d8 ⇒ 5 So 23 to hit
Damage: 1d4 + 3 ⇒ (3) + 3 = 6
Halberd: 1d20 + 5 ⇒ (1) + 5 = 6
Damage: 1d10 + 3 ⇒ (3) + 3 = 6
Halberd: 1d20 + 5 + 1d8 ⇒ (15) + 5 + (7) = 27
Damage: 1d10 + 3 ⇒ (4) + 3 = 7

Ol' Pike |

Pike, growling from the bleeding wound Enizver left in his side, strikes at Horat as he steps forward.
Attack: 1d20 + 8 ⇒ (12) + 8 = 20
Dam: 1d10 + 5 ⇒ (7) + 5 = 12
He strikes the Untherite hard (12 damage). Horat returns with a blow of his own.
Looks like 21 to hit to me but that's fine.

Enizver |

Grunting, Enizver re-aimed at the pirate. He was rather hoping to have killed the seagoing bandit with a head wound, but somehow wasn't surprised. He fired again.
To Hit: 1d20 + 5 ⇒ (11) + 5 = 16
Damage: 2d6 + 3 ⇒ (4, 3) + 3 = 10
Thunder Monger: 1d6 ⇒ 5
Sneak Attack: 2d6 ⇒ (5, 1) = 6

Halgrin |

Halgrin screams in anger, and suddenly his body is awash in radiant fury. He charges at the Captain, ready to drop him.
"Pike!" he bellows as he swings his blade.
Activating Rage as a bonus action. And using Reckless Attack.
Longsword (Reckless) vs Pike: 1d20 + 5 ⇒ (7) + 5 = 12
Longsword (Reckless) vs Pike: 1d20 + 5 ⇒ (13) + 5 = 18
Slashing Damage: 1d8 + 7 ⇒ (4) + 7 = 11
Radiant: 1d6 + 1 ⇒ (1) + 1 = 2
HP 35/35. Rage. Melee weapon attacks against me have advantage.

Olivia "Liv" Moore |

Olivia cries out in pain as she knocked down and then promptly skewered. Her vision starts to go dark. She tries to fight it off but to no avail as she falls unconscious.
I believe Olivia is stable from the medicine check but she remains unconscious.

Ol' Pike |

That's right, Olivia.
AoO: 1d20 ⇒ 16
Dam: 1d10 + 5 ⇒ (6) + 5 = 11
Attacks in rear: 2d20 ⇒ (18, 1) = 19
Attacks E: 2d20 ⇒ (3, 18) = 21
Attacks W: 2d20 ⇒ (15, 16) = 31
Attacks front: 2d20 ⇒ (5, 19) = 24
Attacks H: 3d20 ⇒ (18, 20, 11) = 49
Dam H: 1d6 + 3 + 1d10 + 5 + 1d10 + 5 + 1d4 + 5 ⇒ (2) + 3 + (4) + 5 + (4) + 5 + (2) + 5 = 30
Dam E: 1d6 + 3 ⇒ (2) + 3 = 5
Wis Sanct: 2d20 ⇒ (10, 5) = 15
Dam W: 2d6 + 6 ⇒ (5, 4) + 6 = 15
Dam Hal: 1d6 + 3 ⇒ (1) + 3 = 4
Pike's signature weapon flashes out in front of him as Halgrin approaches, stopping the orc dead in his tracks before he can even reach Pike (11 damage and move speed reduced to 0).
Polearm master+sentinel leaves Halgrin 10 ft away and he doesn't have reach. Because you are stopped 10 ft away and don't have anyone to attack, your reckless attack won't be activated so I won't give enemies adv on hitting you.
Enizver has trouble shooting through the pirates swarming over him and his shot misses. While Horat lands a blow, Wrinil stabilizes Olivia. The two pirates who were aft rush down and attack in the rear. Horat lashes out at one of them as he approaches but misses.
Pike steps to the side and strikes Horat twice with his pike and once with the butt of his weapon. Pirates converge on the deck and Horat is struck again knocking him unconscious. Halgrin is struck once (4/2=2 dam) as is Enizver (5 dam) while two pirates attack Wrinil but are confused when they can't force themselves to strike the innocent-looking man.
Horat, I think your HP aren't updated. But I'm pretty sure you're unconscious at the top of this round. Let's just go with that.
Pike appears to be roaring for reinforcements but no sound is heard. There is, however, plenty of grunting and stomping coming from other parts of the deck. It can't be long before the fight is noticed by those below.
Party, GO!

Horat "The Bulwark" |

I completely missed the second hit in one of the above posts. Horat is indeed down.
Horat blacks out, slumping to the ground unconscious.

Enizver |

"You realize that we're only trying to remove that sea-going tyrant, and if he goes down the ship - and it's loot - will be yours to do as you see fit, right? We just want off the boat."
Still, ignoring them seemed the best course of action in terms of shooting, and Enizver took another crack at the salty old dog.
Persuasion: 1d20 + 0 ⇒ (10) + 0 = 10
To Hit: 1d20 + 5 ⇒ (15) + 5 = 20
Damage: 2d6 + 3 ⇒ (1, 3) + 3 = 7
Thunder Monger: 1d6 ⇒ 6
Sneak Attack: 2d6 ⇒ (4, 3) = 7

Wrinil son of Pel of Waterdeep |

Wrinil says a prayer while holding his holy symbol. Aid on himself, Liv, and Horat. He then whispers to Liv, "On my word, get your broom and you take Enizver and get to port. I'll take care of the rest." For better or worse, the timid Wrinil they once knew might be gone.

Halgrin |

While halted by Pike's attack, he was barely hurt by it otherwise. With an errant slap from his blade, he steps into the pirate's personal space. He snarls at him, and attacks.
Attack
Longsword (Reckless) vs Pike: 1d20 + 5 ⇒ (1) + 5 = 6
Longsword (Reckless) vs Pike: 1d20 + 5 ⇒ (13) + 5 = 18
Slashing Damage: 1d8 + 7 ⇒ (3) + 7 = 10
Action Surge
Longsword (Reckless) vs Pike: 1d20 + 5 ⇒ (1) + 5 = 6
Longsword (Reckless) vs Pike: 1d20 + 5 ⇒ (8) + 5 = 13
Slashing Damage: 1d8 + 7 ⇒ (2) + 7 = 9
Radiant: 1d6 + 1 ⇒ (2) + 1 = 3; Added to 1st attack that hits.
HP 33/35; Rage. Melee attacks against me have advantage.

Olivia "Liv" Moore |

I think we've been doing a 50% chance of acting in a round where we were unconscious and got healed? Going to act with that assumption, but since slides keeps track of history, we can undo that if I'm mistaken. High roll means I get to act.
1d100 ⇒ 53
Olivia groans softly as she starts to wake. Though she's surprised to see that she and her companions still seem to be in combat. That normally wasn't the case when she woke up after such blackouts. She listens to Wrinil's instructions, her grogginess making it hard to figure out what he was planning. But she nodded anyway. I'm guessing 'on my word' was more flavor text and he's not actually trying to get her to ready an action?
She stands shakily (15 ft movement), grabbing her broom before taking off (vertical 15ft movement) and then starting to circle around to where Enizver is Action to dash with broom's 50ft move speed, casting a spell as she goes. Bonus action for 2nd level healing word on Horat
Healing: 2d4 + 3 ⇒ (2, 2) + 3 = 7
If anybody shoots at me (or I suppose attacks with a polearm with 15ft reach), I'll cast Shield as a reaction

Wrinil son of Pel of Waterdeep |

Wrinil grabs her arm before she can take off, "Will you just wait a second?"

Olivia "Liv" Moore |

"You're going to have to give me more than just a vague 'wait'. I'm already about to pass out. Even with my magicks I may not last long enough to enact whatever your plan may be if I just wait around here."
Unless Wrinil actually convinces her to stay by presenting a reasonable plan of action, Olivia's probably going to stick with her stated actions. The only thing I can think of that he might be planning that requires her to be close is to cast invisibility or a cure spell, which seems a lot riskier than her just getting out of reach. I can move less far away though if that's helpful.

Wrinil son of Pel of Waterdeep |

"You, invisible." Wrinil then puts up his hands and faces toward the two crewman, "We surrender, just please don't hurt us."
Deception: 1d20 - 1 ⇒ (19) - 1 = 18
Wow! I'm getting good at this.

Horat "The Bulwark" |

Act on 51+: 1d100 ⇒ 11
Horat's wounds start to heal and he involuntarily groans softly in response.

Pawn's Dilemma GM |

AoO: 1d20 ⇒ 11
Dam: 1d10 + 5 ⇒ (5) + 5 = 10
Attacks E: 2d20 ⇒ (3, 10) = 13
Attacks W: 2d20 ⇒ (20, 17) = 37
Attacks H: 2d20 ⇒ (1, 8) = 9
Attack Hal: 1d20 ⇒ 17
Attacks Horat: 4d20 ⇒ (20, 7, 14, 6) = 47
Dam hal: 1d4 + 5 ⇒ (4) + 5 = 9
AoO Horat: 2d20 ⇒ (3, 12) = 15
Dam W: 3d6 + 6 ⇒ (3, 1, 6) + 6 = 16
Dam Hal: 1d6 + 3 ⇒ (2) + 3 = 5
Dam Horat: 3d6 + 6 ⇒ (3, 5, 1) + 6 = 15
Once again, Pike's skill stops Halgrin 10 ft away where he can't attack the pirate captain (19 to hit for 10 damage).
Map squares are now 5 ft to eliminate confusion.
Unable to reach the captain, Halgrin knocks out one of the nearby sailors. Pike strikes at Halgrin twice more but misses. Then he brings the butt of his weapon to bear and lands a blow on the half-orc (9 bludg before resist). Then he steps back, reeling somewhat from Enizver's last blow, and shouts again at his men "Finish off that gnome!"
His men attempt to comply, stabbing at the gnome, but miss. Two attack Wrinil, both landing solid blows (7 and 9 damage respectively). One sailor lands a blow on Halgrin (5 dam before rsst) and two sailors approach the newly-conscious Horat. Horat tries to stop their approach but misses. Together, they knock Horat back into darkness.
Party, GO!

Olivia "Liv" Moore |

Seems a little game-y to try retconning Olivia's action after the DM updated, so going to stick with Olivia flying away.
Olivia once again attempts to heal Horat before shooting a blast of energy at the captain and moving towards Enizver. "Want a lift?" Wouldn't have enough movement to get Enizver on the broom and move away this round, so I can do that next round. Though I'm also not really sure how getting Enizver on the broom would work mechanically in terms of our actions.
Bonus action: Healing word on Horat. Action: Eldritch blast the captain. Then move (still while 15ft above the deck of the ship).
Healing: 2d4 + 3 ⇒ (4, 4) + 3 = 11
To hit, captain: 1d20 + 5 ⇒ (5) + 5 = 10 Going to assume that misses
Once again, will cast Shield if attacked