This is strange. Are you sure he is not clicking on those mails in his phone? Or somebody else having access to it. Change the password for the email and check again, if this continues then the problem would be either in his phone or imac.
Try with password change and we will see how it goes.
Some of it depends on what type of account @outlook.com accounts are but I am quite sure that it would be IMAP. As such, if you delete your messages, it will delete them from your live email account to, which obviously could come with unintended consequences. To avoid that, I would recommend first confirming that messages are only set to download when you click Refresh. As I don't have Outlook I cannot confirm or guide you on how to do that.
After that is set, I would delete the account from Outlook and then re-configure it. Doing so will remove messages from your computer without deleting them from the cloud. You should then be able to send emails as desired.
The other thing to consider is that unless you are running low on disk space, there is no need to worry about having some unneeded messages sitting in your Outlook application. If it were me, I would turn sync to manual and leave them there, likely.
Edit:
It took me awhile to grasp your question, and it looks like I partly failed. It looks like you don't want your messages sitting around in Apple Mail.app. As such, the above would apply. However, OS X does allow you to set default Mail programs and you can likely set Outlook to that function. With that, you could use Outlook as your primary, and only, email client and delete the account from Apple Mail.
Best Answer
It looks like your fonts got borked somehow. This is most likely to happen if you've recently installed an application that adds or changes fonts, which includes apps like Office, iWork, the Adobe suite, and many more.
I'd start out troubleshooting Font Book. Apple's KB article about Font Book has information about how to address this.
For troubleshooting, I think that you should try them in this order: 1. In Font Book, go to File > Restore Default Fonts. This is the easiest and seems the most likely to resolve your issue, since fonts in email are highly likely to be a default font. 2. In Font Book, validate your fonts (it's under the File menu).
3. In Font Book, check for duplicated font (it's under the edit menu).
Between each of these steps, quit Mail and restart it to see if it works; font changes won't show if you haven't restarted Mail.