re: What's the most amount of money you have ever loaned someone?

800$. I busted this guy in 2-5 no-limit hold em game at Winstar casino in Oklahoma. He asked me for his full buy in + 300 to play in a bigger game. It was a no-brainer. The guy has lifetime earnings that dwarf mine. He repaid it + 200 that same night after winning 2600$ in a 5-10 no-limit hold em game later on.