Hello Jeff Mah,
If I understand you correct, you are using the RadEditor in Sitefinity, and you click on the Insert Document tool, is that correct?
This tool uses a Content Selector (to be precise, Document Selector) which takes the documents of the Document Libraries, and show a list with them to you. Unfortunately the only way to have a list of documents, sorted by some criteria, is to build your own RadEditor dialog, then register it instead of the one we use. There are special set of API functions that can work with the Images and Documents module. We are ready to assist you, if you aim to build a custom dialog. The dialog itself is a aspx page.
the Telerik team
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