This happened about 4 years ago when I was a large, strong purple belt. After a BJJ seminar at the Inosanto Academy in Los Angeles, Jean Jacques decided that he was going to roll with all the seminar participants one after another. Not surprisingly, he went through us all without really breaking a sweat.
In my match with Jean Jacques he first passed my open guard like a hot knife going through butter. I turned and came onto my knees to avoid the pin, but he got on my back with one hook in. When he started fishing for a lapel choke I was determined to defend it well: I was not going to give him an easy tap out! At one point I accidentally hit him in the face with the back of my hand. I immediately apologized and got the ubiquitous Brazilian “no problem, my friend” response.
He then switched to an armbar, with me still turtled and him balanced on his head, face down to the mat. I was defending well, I thought, but after about 20 seconds I realized that my arm was suddenly straight: somehow he had moved it into a perfect armbar position WITHOUT me recognizing it. He was holding it in that position, but not applying ANY pressure to it, waiting for me to realize that he had caught me.
My thoughts at the time went something like this: “I’m defending this, so far so good, to get out all I need to do now is…. wait a second… I’m already caught!” This was so unexpected that I was laughing as I tapped out.
As far as I’m concerned we both won that match. He won it because he got the armbar. I won it because I got to experience rolling with someone who is at a very, very high level of skill. I hope that everyone gets to experience what that feels like at least once in their grappling career.