Portland City Commissioner Amanda Fritz
I became Amanda's webmaster--developer and host--in her first campaign for Portland City Council in 2006. She was the first publicly funded candidate in Portland history, which I suppose makes me the first publicly funded webmaster of a campaign site in Portland history. :)
In 2006, Amanda lost, but I encouraged her to begin blogging at AmandaFritz.com. She did, and it may have helped her with name recognition (at least, I think so) leading up to the 2008 election, which she won.
Her current campaign website was built from scratch on Drupal 7 with CiviCRM; its look (pretty much designed by Amanda) is almost identical to her first two sites. The older websites were originally built on Drupal 4.7 and remain for the time being on Drupal 6 since they are rarely used.