Content of the article: "Party Assassinates Hobgoblin Leader with Magic Pineapple"
We were a level 8 party of 7 tasked with eliminating a Hobgoblin leader who wielded a magic gem which although powerful, made the user turn insane. Earlier in the campaign we'd purchased a magic pineapple which supposedly turned the head of whomever consumed it into a pineapple which retained the aforementioned magic property. Originally we'd purchased it as a joke, the DM clearly intending it to be a joke, but we soon found a use for such an item.
The Hobgoblins were encamped in the outskirts of a major city in our DM's homebrew setting, and we did not want to fight or sneak our way through. This is when one of the party members, I forget who, suggested we use the magic pineapple. We agreed, and continued building on the idea, the DM clearly surprised with the evolving plan. We'd been given a wagon to ride to the city by a baron who we'd helped previously and decided to covert the wagon from one that carries passengers, to that of a merchant's cart, peddling exotic goods.
Our party's Tabaxi bard and myself (a human warlock) would play the role of merchants (for we were the only ones with fine clothes), 2 of the less charismatic party members (and the two NPCs we had in tow) would wait a predetermined location in some woods approximately 500 ft. away from the encampment. The remainder of the party would be wearing common clothing and playing the role of whatever travel companions accompanied travelling merchants.
We'd loaded the newly converted wagon with a bunch of items we'd no need of or didn't ever use, such as a magic +1 dagger, a circlet of blasting, various books we'd picked up. Some of the party members also contributed unused martial weapons and I dumped a collection of mundane items I had been carrying (whetstones, soap, insect repellent).
Because pineapples did not grow in the local climate, they were relatively exotic, hence we planned to offer a sample of pineapple to their leader and watch his head transform into a pineapple, and afterwards we'd make our escape.
As we made our approach to the camp we were stopped and, as expected, asked to explain ourselves. We said we were travelling merchants from far away, selling exotic goods and magic items. After a short wait we were allowed to come inside and their leader arrived to greet us. Initially he was only interested in our martial weapons, but later grew an interest in our magic items. We sold the +1 dagger and circlet of blasting, alongside many mundane items. The Hobgoblin leader even purchased one of our books.
After a while, we felt it appropriate to offer him our exotic snack, and gave him a sample. We were under the impression that a small sample would suffice enough to transform his head into a pineapple. However, the Hobgoblin ate it all without such a transformation occurring. Thankfully he had liked the pineapple enough to warrant a purchase.
Supplied with more magic pineapple, he began to eat more bit-sized chunks while we were debating amongst ourselves whether the 'magic' pineapple was a scam. We were relieved when on his fifth piece, the Hobgoblin froze, and in the blink of an eye his head was a pineapple.
Our plan sprung into motion, and Tabaxi bard grabbed the Hobgoblin leader and used dimension door to teleport to the predetermined location. I did the same with another party member, while the two who couldn't teleport used call stead and rode away unscathed. In the confusion and surprise, the Hobgoblins were unable to offer any kind of resistance, and we escaped. What's more, we easily pried their leader's pineapple head off and got another magic pineapple, alongside the magic gem we were trying to retrieve. We even earned a large amount of gold from the items we sold, and all it cost us was a wagon we'd gotten for free.
TL;DR: Party disguised as merchants turned a Hobgoblin leader's head into a pineapple by selling him a magic pineapple which turns peoples heads into a pineapple. The party then teleported away and escaped to safety.
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