Lenny was always in the crowd. He is african-american and wore a hat and sunglasses.
Yes, I remember him as well. "Lenny", whose real name is Linny Boyette, was always in the crowd and as the camera panned the crowd - he was the man in the hat who gave a thumbs-up to the camera. Meredith even gave him a kiss on the cheek a while back.
He supposedly was so upset when Ann Curry left the Today Show that he moved to Good Morning America. See link.