Ranked-choice voting was enacted by a ballot measure passed in March 2002 and while it's been used before, this election will be a real test.
When Mayor Gavin Newsom (now Lieutenant Governor) was re-elected in 2007, it was a ranked-choice election but the field of candidates included folks like George "The Naked Guy" Davis. Newsom received more than 73 percent of the first-choice votes and no second round was necessary.
This time around it will be different. There are lots of candidates to choose from and no clear front-runner. It could be a repeat of a recent Oakland election where after a few rounds a dark horse candidate actually won the mayor's office.
Ranked-choice voting is essentially a plurality system that is designed to pick the most popular candidate.
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If you're interested in learning how ranked-choice voting works in San Francisco - click here for a short demo. The New York Times ran an article in November 2010 (after the election in Oakland, California) whose headline read "The Winning Strategy in Oakland: Concentrate on Being 2nd or 3rd Choice. California Watch ran a story in October 2010 entitled "Ranked-Choice voting complicates elections." One of the national organizations behind ranked-choice voting is Fair Vote and you can visit them here.