did something look a little funny about his tail?
(tongue planted firmly in cheek)
That's a common condition for an older buck. It's called chronic buck-tail atrophy. In short, older bucks like that are so good at sneaking around they never get jumped or startled, which leads them to never raise the flag and flee, which leads to the muscles that control the tail weakening to the point they can no longer raise their tail. I bet the underside of his tail is brown instead of white......
GH