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Even better is when that one guy is the DM
I try to win as the DM.
"Winning" in this case being that everyone had a good time.
You sound like a good DM
WIN AT ALL COSTS
FUN IS MANDATORY AT MY TABLE
I SPECIFICALLY REQUESTED IT
So says Friend Computer.
Oh, you don't want to take a path with an obvious trap? Well a level 20 red dragon swoops from the sky and attacks your level 1 party. Roll initiative!
And as a player who wants to do that too, I keep in mind that the DM is also playing the game and wants to have a good time.
Thank you! This is something that many people forget, both players and DMs.
It's really the crux of a lot of issues with D&D, from table problems to game problems to publisher problems.
I've been playing in a game with my 11 year old nephew as the dm for the last few months and he's like this. He's great at the storytelling aspects of it but he gets pissed when we try to strategize before a fight and I somehow get critted at the beginning of every encounter.... I ignore it because he's a kid and I want to support him but I'd be lying if I said it wasn't getting old.
Talk to him till he is still young and malleable. People sometimes transform into the worst and if that happens only thing I can do is walk away with regret I didn’t nudge them before
I talk to my brother about it and he's working with him but I don't feel comfortable being too hard on him myself. He doesn't have a lot of interests and I don't want to be the one that screws this one up for him.
One way you could maybe handle it is by discussing fudging roles in a way that isn't directed at him. Just talk to the group out loud about the temptation to fudge rolls, but that it takes away from the fun of the game for everyone. He'll hear it and likely understand, but it won't be calling attention to him.
I agree with you, but there have absolutely been games (specifically in Pathfinder 1E) that I had to approach from a mindset of trying to win. PCs can get so ridiculously overpowered in that game that it can be difficult to balance combat properly and sometimes requires you to pull out all the stops to make combat encounters engaging.
Ugh, I've played with DMs who think it's a game between them and the players, where their objective is to kill all the players without making it obvious that they're doing that. Look, man. You're literally God of this world, you don't need to try to prove that you're tougher. Frickin weirdos.