I've got a number of incidents competing for worst, which will probably mean multiple posts, against NPCs of varying significance. Here's a small sample.

Spoiler: Stealing from Pirates
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On the total chump side, there were some space pirates that got snookered hard by the PCs in my Schrodinger's Hummingbird game. Some short preamble, necessary to understand it - the way FTL worked in that setting was with jump drives which made single large teleportations, then needed to recharge for anywhere from half an hour to an hour (depending on quality). The PCs were hired to get some valuable and volatile cargo back from some space pirates that had stolen it from Apollo Mining Company, and found that the pirates had built a temporary space station of three large ships around the cargo container, so they could warp it out and work on it at length, before some military inevitably decided to just blow both them and the cargo up. The PCs pretended to join them, and the ship engineer in particular managed to get in as a jump drive specialist engineer, working on the jump drive. So they get the container "ready" to jump with the pirate ships, modulating the drives to the new shape, while they're on their own ship ready to jump with them, having "joined" the pirates.

The pirates jump, leaving the container behind. Then, the PCs do a quick attachment and start towing the cargo away, trying to reconfigure their jump drive to the new shape while the jump drive is recharging. The pirates come back in about 45 minutes, pissed off, and fire a massive salvo of missiles at the PC's ship, which at the last minute gets the drive calibrated. They jump right before impact, and the three massive warships full of pirates watch as a tiny modified cargo ship vanishes with the equivalent of tens of millions of dollars of exotic minerals they used to have.


Spoiler: Eddie Two Shoes
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Among the space pirates the Schrodinger's Hummingbird crew pissed off was Captain Edgar Twinbarrel, an impetuous hothead. This is his story, in multiple incidents, where the PCs ran circles around him in hilarious ways. He had a small warship a bit larger than the Hummingbird, went up against it several times, and consistently lost. The fun part is how.

The first incident was a space battle. Edgar made demands that the PCs surrender the Hummingbird, they refused, and a fight started. They then proceeded to hack Edgar's ship coms, and project their insults back to the entire crew, most notably having the ship janitor repeatedly call him "Eddie Two Shoes". He gets angry and fires every single missile a little close together, the ship gunner blows them up in a chain reaction, and then they send a mocking message about how "Eddie Two Shoes" was clearly incompetent and should listen to junior officers, correctly guessing that they'd warned against him. They then proceeded to cripple the ship, loot it, and leave.

The second incident was a bit later. The PCs managed to talk some officials into putting up a bounty on Edgar that they could collect, but the way they portrayed him ended up changing the bounty on both him and his first mate, Roy Colt, such that Roy's bounty was higher. When they went to collect they immediately sent a message to the effect of "Hey Eddie, look at this" along with the two bounties. This was a mixed victory in that they were only able to get Roy and then leave, but as they did that they sent a message (again to the entire crew) about how they'd got the bigger bounty. Edgar was not pleased.

Then there was the final encounter. The Hummingbird had been upgraded pretty significantly, it's crew was better at their jobs, and most notably they had a pretty nasty computer warfare suite. They go after Edgar to collect his bounty, have a bit of a firefight, and once they've taken out the missiles and can hide from beam weapons for a while manage to not only take comms but also life support, and start venting atmosphere. They then tell the crew that they'll give life support back if they hand over Edgar, specifically if they put the new first mate who they admire professionally in charge instead. The pirates end up mutinying to get their breath back, and Edgar's last memory before a life of incarceration is his crew handing him over in chains to a bunch of gloating mercenaries.


Spoiler: A Sword and Its Fencer
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Estella Belmonte was the nice and primary enforcer of Javier Belmont, campaign primary antagonist for Port Alhabri. She's also a serious contender for the best recurring antagonist I've ever had (albeit one of two from that campaign), a menacing leader and serious thorn in the side of the PCs, who were various alchemist-adjacent people formerly of a now disbanded alchemist's guild destroyed by her uncle. She led a raid on the PC's last allies in the cities, severely wounded some of them, and eventually drove them to flee. That should have been the last they saw of her, until they came back.

But someone stole her sword. A new masterpiece made by a master smith, about to be handed to her, stolen from under her nose. She didn't know who it was until later, when following the PCs to their ship as they fled port, her moment of triumph. Then they took the sword out, and slowly waved it in the air, so that she could see it.

So like the violent, volatile, petty hothead she was she found them halfway across the world and decided to follow them. Like the surprisingly clever schemer she also was, she then wrought havoc through catspaws, and eventually ended up in a duel with the group's best swordsman, the one real combat monster in the group. It was an even match which could have gone either way, and she won, killing him in front of his second. That was the last straw.

This group, already alchemist adjacent, managed to acquire an actual foreign alchemist. They shared what trade secrets they knew to brew up a batch of alchemists fire, and by "batch" I mean something akin to "industrial sized batch reactor". They learned that she took a particular route through a wealthy neighborhood full of tall stone walls and narrow roads, and took their revenge. Hiding behind several walls with enormous amounts of alchemists fire they let her enter a T crossroad, sniper on the roof with a musket. Then they threw fire. They cut off all three escape routes one at a time with huge walls of fire, and when she tried to climb the far wall they shot her in the hand. Unable to climb she died slowly, terribly, of smoke inhalation and the heat of encroaching flames.


Spoiler: Some Mooks Are Smarter Than Others
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On top of these there were some miscellaneous one sided fights which were just hilarious, and kind of humiliating for the losing side. Sticking to the two campaigns already somewhat explained here:

The Schrodingers Hummingbird has taken a lot of attacks against it, and perhaps the most ill advised was a jetpack based boarding scheme. Done on a minimal budget the idea was to pack a bunch of jetpack equipped mercenaries in a small vehicle, give them all hull cutters and guns, and have them cut through the hull and swarm inside, where the small crew of 5 would be overwhelmed. What actually happened was a little less impressive. Half the mercenaries got shot to pieces by a turret gun, the ship gunner being an expert. One got taken by a cargo hauling harpoon, a discount tractor beam never intended as a weapon. Still, the hull cutting started, and it might have gone well - had some of these mercenaries not decided to try and go through the cargo bay doors. They were opened outwards to hit them and fling them into space, and the rest decided to just flood through before they were closed, not thinking of why, exactly, that tactic would even be tried.

That reason would be the small, single person fighter currently in the cargo bay, pointing backwards towards the cargo bay doors. By space ship standards it had a sad little laser, as befits a ship small even by fighter standards. By space suit standards, this was a machine gun nest with armor piercing rounds. So ended the boarding party.

At one point in the Port Alhabri campaign, the PCs and their allies in the civil war they accidentally got involved in* were besieged in a castle. Their resources were an alchemist trained in alchemists fire, here largely unknown (though there were rumors after what had happened to Estella), a small force of soldiers, and a roost of a lot of carrier pigeons. You know, for letters, to get reinforcements or whatever.

"Or whatever", in this context, turned out to mean that they were trained to "deliver" small vials of alchemists fire to midair, a bit above bow range and right above enemy soldiers. That whole battle ended in one stroke, and that stroke was pigeon bombing.

*Basically started, but it was long coming.




Later: I have a story from my Nomad's Gift campaign, involving magical lava artillery, a villain with a history of crimes against humanity, and transport by balloon.