I just found out about Stu Rasmussen, America's first openly trans / genderqueer mayor. That right there is cool enough--in fact, I'd be delighted that somewhere some big city had elected a handsome, f2m guy, but it gets better.
First of all, Rasmussen's identity is complicated and difficult to ignore--he identifies as male, is biologically male, wears "female" clothing and had breast augmentation surgery (see here for his very funny description of it). So these aren't folks turning a blind eye to something that they'd rather not notice, these are folks clearly and unambiguously voting for someone who is Not Like Them.
The other thing I really like is that it wasn't a big city at all--it was Silverton, Oregon, population 7,400. He* was elected after running a campaign based on small town values--damn right. Here's the Coilhouse entry with a video interview.
*I really hate the current gender-neutral pronoun options, and unless the person in question expresses a preference I'd rather find another possibility. Rasmussen identifies as male in the video, so I stuck with "he". She uses "she" in the Tapestry article, though. I wish I felt more comfortable with ziring people...