The first time we heard anything about there being a problem was on February 1, 2001:
On February 15, 2001, the following letter arrived, addressed to Todd Fries, holder of the OpenSSH.com domain. Other than holding that domain, Todd Fries has nothing to do with the OpenSSH project. The domain is in the process of being transferred to an OpenSSH developer.
Note that the US trademark is on a logo; that logo being a graphic containing the lowercase letters "ssh" in a special font.
The United States Patent and Trademark Office also has a web friendly entry about this trademark at: http://tarr.uspto.gov/servlet/tarr?regser=registration&entry=2141991. Unfortunately, that search engine provides incomplete information and does not detail the actual mark status, but other unlinkable searches engines in the USPTO database will show the mark to be listed like this:
"(5) WORDS, LETTERS, AND/OR NUMBERS IN STYLIZED FORM"
OpenSSH doesn't use that particular style (Hey — we've got style, just not that kind of style).