<meta itemprop="image" content="http://www.caskeybeats.com/uploads/3/9/6/9/39697620/youtube_orig.jpg>
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Unfortunately because the tag immediately before the Twitter cards markup is malformed (there is no closing " in the content attribute), the rest of the document is malformed from the perspective of our crawler, so the cards tags are ignored. If you fix that, it should work fine.