Thanks for everyone's insights and opinions, I think I'll try and have a long conversation with him about a middle ground we can both get behind, that way he can still play how he wants and I can get what I want out of our games. Just a few thoughts, first and foremost, I may have misused the phrasing "That guy" I know it means different things to different people, and to me and my friend group it just meant more that someone was more interested in winning rather than having fun. Not that he has ever cheated or done anything wrong, but his focus is almost always on winning rather than having what I would consider a "good game." He has literally ran army lists he openly admits aren't fun to play against or are fun for him to play, but he runs them anyways because they win. Another example would be there have been times where I would obviously be the winner due to a double turn, and I've just given it to my opponent to make it more enjoyable for the both of us. Most, if not all the time where that was the case for him, he would just take the double turn and I would lose to no one's surprise. There are other small things like that, and again, he didn't do anything wrong, it's just...boring sometimes. As for the folks suggesting just not playing with him, I'm not sure if you missed the part where I talked about how small my gaming group is? I don't live in a podunk town, but our AoS group around here is fairly small, before he joined my group of friends I'd get in, maybe 2-3 games a year, now, we play almost every week. So if I choose not to play with him, I might as well just be choosing not to play AoS (40k is much more popular around here and even then that group is small). As for skill levels, I'd say he definitely has more of a mindset for competition than I do, I mentioned he watches a number of podcasts and reads a lot about tournaments and such, he actively enjoys doing the math on values of units and who is best at what. So in that regard, he probably is better than me, he see's what is best from a numbers standpoint and goes for that. I, on the other hand, live by the rule of cool. Not to say I can't tell what is and isn't good for list building and see synergies and all that, but when I see Archaon or a Hellpit Abomination, I'm of the mindset that it'd be cool to see those on the table, not whether they are the most competitive models. I love running fluffy lists that have my favorite models and characters in them knowing full well they aren't the most competitive, but they make for a fun game assuming they dont all die turn 1. So yeah, main point being, I just need to hash out some of this with him so we can both find some enjoyment from our matches, I appreciate the input of those who read my post and understood what was happening and your words of advice!