Chiafalo supported the 2016 presidential campaign of Bernie Sanders. He publicly stated he might not vote as pledged for Democratic presidential nominee Hillary Clinton and vice presidential nominee Tim Kaine.
When the Electoral College voted on December 19, 2016, Chiafalo became one of four electors from Washington (along with Levi Guerra, Esther John, and Robert Satiacum Jr.), not to vote for Clinton. Instead, he voted for former U.S. Secretary of State Colin Powell.
Chiafalo considered himself a member of an ad hoc group known as the "Hamilton electors". Their plan was to find enough electors, on each side, to deadlock the Electoral College, so it failed to elect either Donald Trump or Hilary Clinton. If the Electoral College was deadlocked they believed they next US President would be elected by the Representatives elected to the lower house of the US Congress.
- Faithless electors in the United States presidential election, 2016
- List of United States presidential electors, 2016
- Mike Padden, 1976 Washington faithless elector
- Raftery, Isolde (December 15, 2016). "This 19-year-old elector is prepared to take down Donald Trump". KUOW. http://kuow.org/post/19-year-old-elector-prepared-take-down-donald-trump. Retrieved December 20, 2016.
- O'Donnell, Lilly (November 21, 2016). "Meet the 'Hamilton Electors' Hoping for an Electoral College Revolt". The Atlantic. http://www.theatlantic.com/politics/archive/2016/11/meet-the-hamilton-electors-hoping-for-an-electoral-college-revolt/508433/. Retrieved December 20, 2016.
- Brunner, Jim (December 19, 2016). "Four Washington state electors break ranks and don’t vote for Clinton". The Seattle Times. http://www.seattletimes.com/seattle-news/politics/four-washington-electors-break-ranks-and-dont-vote-for-clinton/. Retrieved December 19, 2016.
- Jim Camden (2019-01-23). "Washington Electoral College electors who shunned Hillary Clinton to stop Trump fight fines in Supreme Court". The Spokesman Review (Olympia, Washington). https://www.spokesman.com/stories/2019/jan/22/washington-has-one-fight-left-from-the-2016-electi/. Retrieved 2020-05-08. "Chiafalo, who supported Democrat Bernie Sanders during the primary process but signed the pledge to vote for Clinton after he was named an elector during the state Democratic convention, became part of a group calling itself the Hamilton Electors. They said they were willing to vote for someone other than Clinton if enough Republican electors in other states would vote for someone other than Trump. Without a majority for either candidate in the Electoral College, the election would have been sent to the U.S. House of Representatives."
- Jim Camden (2016-11-30). "Washington Electoral College elector willing to switch his vote". The Spokesman Review (Olympia, Washington). https://www.spokesman.com/stories/2016/nov/30/washington-electoral-college-elector-willing-to-sw/. Retrieved 2020-05-08. "There are, at this point, six Hamilton Electors, by Chiafalo’s count. But all are Democrats, so if they cast their vote for someone other than Clinton on Dec. 19, Trump still wins. To keep the Republican nominee from being declared president, they will need to persuade at least 37 Republican electors in states that gave a majority of their votes to Trump to switch to someone else."
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