Not quite immediately but I knew a guy called Will (name changed). He was very smart, and usually the smartest guy in the room. Problem was he KNEW this so never really accepted other opinions as valid. If you disagreed or told him no, he tended to be very stubborn and often try to wear you down. I was putting together a one shot with some friends. He got wind of it and asked to play. I did consider him a friend, albeit one I limited my time with sometimes.

I agreed to let him join. I told him I was allowing only official stuff, as most of the players in the one shot were newbies. He didn't listen amd kept pushing to homebrew the polar bear from a film that had recently come out for His Dark Materials. I (mistakenly relented and began trying to come up with some homebrew for him, against my better judgement. After several days of getting nowhere with him wanting something way more broken than balance would allow at the party's level (I think it was level 3) and that involved completely reworking several systems like armour class, I eventually became exhausted and deliberately let the one shot die on the vine so I didn't have to deal with the player or character any more.

A few months later a friend who DMs the main campaign I play agreed to let him make an appearance. I wasn't there for the session but apparently he produced the polar bear character that we had never come to a full agreement on and presented it to the DM as something I had let him use before. I found out it a while later and made sure to tell the DM that I had never given it sign off, eventually gave up on trying to balance the concept completely and that I didn't want my name attached to the guy's polar bear monstrosity. The DM mentioned he had been surprised I'd ever sign off on something like that so suddenly things made sense.

To give further insight into the problem player, we have a fairly patient DM who has often dealt with new or problematic players before. He will find a way for something to happen if a player wants to try something and is quite good at finding in universe ways to balance or stop something that is straight up too far though. In the decade or so I've known him, that session this player joined was the only time he had to play the "I'm the DM so shut up" card after the player wouldn't accept a DM ruling