I have known Matt from the start of his attending search conferences in the early 2000s. He was always helpful and quick witted in the numerous conversations we have had. I loved watching the gaggle of Cuttlets follow him around every show - and his patience and generosity amazed.
My best memory was when I had written an article for Search Engine Watch - Matt Cutts: Can You Help A Brother Get A lap Dance. It was a post asking about how to legitimately do SEO for the adult industry. I outlined my thoughts on how to be successful and after it posted Matt wrote a reply which was as long if not longer than my article. It went live during a SES San Jose conference and he came up and asked me why I had not approved his comment.
I raced to a laptop to read and approve it... after a few months and the article started to rank his name with adult terms SEW removed the comment - which I fully understood and approved.
I don't think Matt cared, but it was a time when we were much more supportive of each other.