From what I saw of him in 2004 he looked to be 3.5. So in the top pic that would put him at 4.5 and harvested at 5.5.
I've said it before, if you want to start talking about trophy status of a buck, lets start taking pics of their teeth.
No offense but you said it yourself, unless the deer was aged then we don't know how old he was in the top photo. He could have made that jump from 3.5 to 4.5 which wouldn't be unprecedented but a jump like that from 4.5 to 5.5 would be extremely rare.