Yes, this is possible. Following are the steps to do it, but have in mind that this wors only in Internet Explorer. There are issues in other browsers with this approach, and they will be fixed in the upcoming Service Pack (end of March).
Do the following steps:
1. Upload PDF file in the Files folder in the File Manager
2. Create a page
3. Add Generic Content control
4. Edit Generic Content control
5. Insert an image in the Rad Editor
6. Select the image and click on the "Insert a link" icon
7. Click on the "Select a page from this site" link for the "URL address" field
8. Select PDF file from the File Manager and press "I'm done" button
9. Click on the "Insert" button in the "Insert a link" dialog
10. Click on the "I'm done" button for the "Generic Content" control
11. Publish the page.
If you have any problems, don't hesitate to contact us.
the Telerik team