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

$10,000 to a friend to keep his business afloat. He repaid me over the course of 36 months. If he ever missed a payment the contract we had drawn up stated that I would get the business. That SOB never missed, which I thought he would. But I was glad it worked out for him. I didn't charge him interest though, because I'm cool like that.