I actually like Jay. He's been nothing but nice to me when I met him, never turns a fan down, had a great physique and was super professional in almost all aspects of life. I do think as he's gotten older he's become less mature (wearing backwards caps and dressing like a teenager), but I think that's his midlife crisis, especially after Kerri left him.
When I started lifting I never aspired to be big or anything close to a bodybuilder, but as I researched weight lifting more and more I came across pro bbing and the IFBB. Jay was the reigning Mr. O back then and I felt like I could relate to him. He was a blocky white guy who had structural flaws, but worked hard enough that he came in amazing conditioning with size to match. I have a blocky waist and other structural flaws, so I could never relate to guys like Flex (Lewis OR Wheeler, for that matter), Cormier, Wolf, etc.. But I could relate to Dorian, Jay, hell, even Ruhl.
Jay was great for bbing, at least I think he was, he's someone I aspired to look like, even though that probably will never happen.