I dunno, but what about losing the hyphens? Or changing to underscores?
Invalid Username

http://www.chess.com/members/view/skipper
The name without hyphens is in use so must be the hyphens, they're usually ok but maybe you can't start the name with a hyphen.

www.chess.com/members/view/-waller-
Starting a username with hyphens doesn't appear to be a problem.

They probably go tired of suffering from SQL injection attacks and changed the policy to disallow starting with certain characters. No doubt -waller- made his account before they learned this very basic web site security precaution.

Just found it on the support page: Please note that usernames are a minimum of 3 characters and a maximum of 20 and you cannot have any spaces or dots in the name, nor any special characters like ^ & * ! " £ $ % ( ) + = ? / \ |
It can be either one whole word, or use a dash (-) or underscore (_) as a separator.

I think the letters and numbers of a username must be unique, ignoring any other characters, so if Skipper is taken, you can't use -Skipper-, s.k.i.p.p.e.r, _skipper_, etc., but 0skipper0, or sk1pper would be fine.
Or maybe there is a requirement that a username starts with a letter rather than a symbol.

I sent in a ticket to chess.com support, and received the following response:
"Nate,
Thanks for writing in. The username needs to begin and end with a number or a letter."
While attempting to change my username to -Skipper-, I encountered the error message "invalid username, please try again."
Are there restrictions on the use of certain characters? I checked the members page, and this username has not yet been claimed.
-Nate