Dungeons & Dragons Online

How do I handle a player who prepared too much?

This require a little bit of context I think. Gonna do the best I can to summarize without leaving a book of text. Minor TOA spoilers ahead. Running TOA with some homebrew mixed in. My group had multiple backstory plot line hooks in Jahaka Anchorage, so they were going there to fake as slave buyers, buy one of my characters mother's out from slavery, and then allow my other player to renounce his pirate background and burn the port to the ground. He has been working as a double agent, feeding the info the pirates and Liara have given him back into Port Nyanzaru, working against his childhood best friend turned pirate captain.

They get to the port and everything is basically empty. I've laid a trap with Xandala, a character from the module who was with the party for a few sessions but had been kicked out for being shady. She went and betrayed the group to the pirates so they knew the group was coming. My group splits themselves, one player to talk with his pirate contact, the others to go look at the slaves. I then reveal that they've been tricked, have Xandala drop her disguise, tell them that they'll make great slaves for the Yuan Ti when they come back to buy, and end the session.

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We pick up the next week, and my player stops me before I go outside with him bound and gagged to the rest of the group. He has written a giant monologue to say to try to convince his pirate contact that he is not the rat, but Xandala is. I'm very flattered that he would have done this I listen to part of it, and tell him to roll deception. I would've normally given him disadvantage because of the situation, but I made it neutral because of the effort put in. It's bad. I tell him to step with me outside and proceed with what my plan was, but I whisper in his ear that we will speak later away from Xandala, since she was right in front of us. My player gets very frustrated after all this happens, telling the rest of the table that everything he wrote was for nothing, and that he is bad at the game. I brought him back in for questioning alone and had good rp at that point, but I could tell his enthusiasm for the situation had been destroyed. T

On one hand, bravo for putting that much effort into the game. I am extremely flattered, but I couldn't just have a pirate who has just been double crossed immediately change tune with a good monologue. The game, at its core, is about dice, and in certain situations I might allow it, but this dude is ruthless. I was going to tie the PC to the front of the ship and sail him out to sea without that speech. Instead his heart was softened and he put him into jail with the rest of the party (the party surrendered and was arrested by the pirates shortly after the failed monologue). Should I just tell the player that his words definitely had an impact on my decisions, even though it might not have been evidenced at the table? How do I encourage this type of planning in the future even though it might not come to fruition? I kind of felt like my player had a small taste of dming when his brilliant monologue didn't go to plan.

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