No one can and we won't be able to until V3 is rolled out next month.
http://www.chess.com/forum/view/help-support/unable-to-delete-messages
Can't Delete Messages?
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@DeDoler:
V3 is short for Version 3 of chess.com. Turns out that the much touted ground up redesign of V2 two years ago was just putting "lipstick on a pig" and V3 is necessary. Because all of the chess.com programming resources are focused on this, problems with V2 are being pretty much ignored. The new target date for release is August.
I've also noticed that when you archive unread messages they continue to show up on the unread badge.
Here, read this:
JUL 11, 2014 | 12:16AM PDT
Naomi replied:
Hello Jamie,
I’m very sorry for the inconvenience, we recently had to make some changes to the messaging system in preparation for the new site version release. Messages for the time being will not be shown as deleted but they will auto-delete once the messaging system is integrated completely. Everything will go back to normal when v3 is released :)
I’m recalling now that I responded to you in the forums!
What I didn’t tell you in the forums is the auto-deletion, so anything you “delete” now, will just poof away when it’s updated :)
Have a lovely day Jamie!
Naomi (Blackenne)
Member Support
This was helpful. I just hope I can start deleting messages soon cause it gets annoying of all those messages clogging up my page.
I once had a massage that I would like to delete. A painful memory now.
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Did you notice that you can't delete your messages any longer? I, personally, was regularly deleting my messages, why this option is removed? Do any of you experience the same problem?