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Read his diaries and he was a very busy young cat. Also realized you were Canadian as soon as I saw the reference to Boxing Day. I was born there and now live in the US. No one here knows what Boxing day is.
That cast came off dozens of times! He would shake his paw and it would fall off and I'd thread it back on and within minutes it would be off again! But you're right: he was very content in that picture and most of the time, he's a very laid back cat. You can read his diaries on my website: www.thedailymews.com Click on the picture of him when he was a kitten on the home page where it says 'Kitten Diaries' and you'll read all about his exploits.
The good thing is that cats have a very high tolerance for pain. He looks content.
Poor baby. He has gorgeous markings.