Until this moment I assumed .ms was a Microsoft TLD, but indeed it is not https://en.wikipedia.org/wiki/.ms
In fact, here we have the ma.tt website, where the ".tt" is Trinidad and Tobago. Is Matt Mullenweg from Trinidad? No!
And that's before we get into the really weird not-a-proper-country ones like .im or .pn.
At the time it did not break the rules. It's breaking the rules now because by the original rules it should have been phased out. What makes it survive is a special arrangement.