Hi,
Does the Trash you mentioned refer to the Junk E-Mail folder?
Assuming it does, please test this issue using web access of your email. Will the deleted message go to Junk E-Mail folder using web access?
In addition, please try to run Outlook in safe mode and test if its caused by add-ins.
To do this, press Windows key + R, type outlook.exe /safe in the Run box and press Enter.
If the issue would be gone in safe mode, please go to File > Options > Add-ins and disable the suspicious add-ins.
Also, please try to create a new mail profile to test the issue.
http://support.microsoft.com/kb/829918/en-us
If I have misunderstood something about the Trash, please feel free to let me know and provide more information about this issue, Ill follow up on this issue.
Thanks.
Steve Fan
TechNet Community Support