I have run into this in two places now. In a search result summary and also in Blog Summary. Here is the scoop:
When a content editor places an Image to be the first item in the Content Window in the WYSISWYG, when you try and use one the of the methods like $Content.Summary() etc...it does not really act as you may like. I have toyed with the idea of a new method that would parse out the <img> or a <div> etc...
Has anyone else run into this issue? What did you do for a solution.
PS: For the blog as a quick work-around I created a new field call "Excerpt". This is manual solution on the part of the content editor though as they would have to complete the field. This solution doesn't work for the Search Results though.